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Chicago
🇺🇸 United States · Central and South

Chicago

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📌State
Illinois (Chicago, United States). It is the third most populous city in the country, with about 2.7 million inhabitants (more than 9 million in its metropolitan area), on the shore of the huge Lake Michigan, in the heart of the Midwest. It is the great metropolis of the central United States: birthplace of the skyscraper, capital of modern architecture, city of blues and jazz, of the Cubs and the Bulls, and a major financial, cultural and transport hub. They call it the 'Windy City'
📌Service city
Chicago itself has everything. It has two airports: O'Hare International (ORD), one of the busiest in the world, and Midway (MDW), smaller and closer in. It has the 'L' public transport system (a partly elevated metro, run by the CTA), commuter trains (Metra), buses, Union Station, hospitals, tourist offices and a wide range of hotels. It is a major rail and air hub for the country, and a base for exploring the Great Lakes region
📌Best time to go
Summer (June to August) is the best and liveliest time: warm weather, festivals, beaches on the lake, terraces and outdoor life, although it is high season. Late spring (May) and autumn (September to October) offer pleasant weather and fewer people. Winter (December to March) is very cold, windy and snowy —Chicago is famous for its harsh winters beside the lake—, with Christmas charm but tough conditions
📌Suggested days
Two to three days covers the essentials: Millennium Park with the 'Cloud Gate' (the Bean), the Riverwalk and an architecture tour along the river, the observation decks (Willis Tower or 360 Chicago), the Art Institute, Navy Pier and a walk along the lake. With four to five days you can add more museums (Field, Science and Industry, the Aquarium), neighborhoods like Wicker Park or Pilsen, a baseball or basketball game, and a night of blues and jazz
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🌤️ Weather in Chicago
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Chicago is the great surprise of the United States: an imposing yet surprisingly friendly metropolis, looking out over a lake so big it feels like a sea. Here, in the heart of the Midwest, the skyscraper was born, and the city became a kind of open-air museum of the best architecture in the world, with work by Sullivan, Mies van der Rohe, Frank Lloyd Wright and so many others. Its skyline reflected in the river and in Lake Michigan is one of the most spectacular on the planet, and seeing it from a river cruise is one of the finest urban experiences there is.

But Chicago is not only architecture. It is Millennium Park with its shining 'Bean' reflecting the whole city; it is the Riverwalk and the urban beaches along the lake; it is one of the world's great art museums, with masterpieces of Impressionism and American art. It is also a city of deep popular culture: birthplace of electric blues and of a legendary jazz scene, a city of sporting passions (the Cubs, the Bears, Michael Jordan's Bulls), and of its own flavors like the famous deep dish pizza and its hot dog. It has the hard-working, warm character of the Midwest.

This guide covers the essentials of Chicago with a practical and warm eye: how to enjoy Millennium Park and the Riverwalk, which architecture tour to choose, which observation deck to go up, which museums to visit, how to get around on the iconic elevated 'L' train and how to experience its music and food scene. Chicago tends to win over whoever visits: it is big, beautiful, cultured and deeply enjoyable.

📖 History of Chicago

The name 'Chicago' comes from a word in the Miami-Illinois language ('shikaakwa'), which referred to a plant of the onion or wild garlic family that grew in the marshy area beside the lake. Before the Europeans, the region was home to peoples of the Illinois Confederation and, later, the Potawatomi. The first permanent non-Indigenous settler was, notably, a trader of Afro-Haitian origin, Jean Baptiste Point du Sable, who settled at the mouth of the Chicago River in the late 18th century and is recognized as the city's founder. Its strategic location, at the point where the Great Lakes system almost connects with the Mississippi basin, made it a key hub. The city was incorporated in 1837 and grew explosively with the railroads and the grain and meat trade, becoming the great center of the Midwest. In 1871, the devastating Great Chicago Fire destroyed much of the city; its rebuilding gave rise to extraordinary architectural innovation and to the birth of the skyscraper. In 1893 it hosted the dazzling World's Columbian Exposition. In the 20th century it received great waves of migration —among them the Great Migration of African Americans from the South, which brought the blues—, lived through the gangster era of Prohibition (Al Capone) and established itself as the cultural, architectural and financial capital of the country's center. The full story is on our history page.

Read the full history ↓

🏛️ Chicago is in Illinois

The 'prairie state': heart of the Midwest, land of the great prehistoric city of Cahokia and of the Illinois confederation, home of Lincoln and of Chicago, cradle of the skyscraper on the shore of Lake Michigan.

Read the history of Illinois →

🗺️ What to see

1
Millennium Park and Cloud Gate (the 'Bean')
Chicago's most famous park, with the mirrored 'Cloud Gate' sculpture that reflects the whole skyline.
Millennium Park is the most celebrated and best-loved public space in Chicago, a modern park full of art right downtown, beside Lake Michigan and bordering the great Grant Park. Opened in 2004, it has become the city's tourist heart and meeting place, a must for any visitor. Its star attraction is Cloud Gate, the sculpture by artist Anish Kapoor that everyone knows as 'The Bean' because of its shape. It is an enormous surface of polished stainless steel, with no visible seams, that reflects the Chicago skyline, the sky and the people who come near like a curved mirror, creating distorted, fascinating images. Walking under its arch and seeing yourself reflected in its surface is great fun and the city's obligatory photo. The park also holds other gems: the Jay Pritzker Pavilion, a spectacular open-air amphitheater designed by Frank Gehry, with its characteristic burst of steel ribbons, where free concerts are held in summer; the Crown Fountain, two glass towers that project the faces of local residents and spout water (kids get soaked in summer); and the Lurie Garden, a beautiful garden. In winter, there is an ice-skating rink. Getting there: right downtown (the Loop); by 'L' train to several nearby stations, or on foot. Best time: summer for the concerts and outdoor life; any time for the Bean. Tips: go early to photograph Cloud Gate with fewer people; combine it with the Riverwalk, the Art Institute (next door) and a walk along the lake. It is free and open all day.
ℹ️ Distance: Downtown (the Loop), beside the lake; 'L' train to nearby stations or on foot · Best time: Summer for the concerts; any time for the Bean · Admission: Free (open access); winter skating separate · Duration: 1 to 2 hours
2
Architecture cruise on the Chicago River
The best outing in the city: a river cruise taking in the skyscrapers with expert guides.
The architecture cruise on the Chicago River is, for many, the city's best experience and an unmissable activity. Chicago is the birthplace of the skyscraper and one of the world capitals of architecture, and there is no better way to appreciate it than sailing along the river that crosses downtown, surrounded by spectacular buildings rising on both sides, while an expert guide tells the history, styles and stories behind each one. Over the course of the trip (about an hour and a half) you see dozens of architectural landmarks spanning more than a century of design history: from the first skyscrapers of the Chicago School to modern glass towers, taking in art deco gems, buildings by Mies van der Rohe and contemporary high-rises. The river offers a unique perspective, looking up at those canyons of steel, glass and stone, along a route of drawbridges that is part of the spectacle in itself. There are several operators; the most prestigious are the cruises guided by the Chicago Architecture Center, with very well-trained guides, although there are other, more touristy or party-oriented options. It's an activity that appeals to architecture enthusiasts as much as to anyone who simply wants to enjoy the views and understand the city. Getting there: the cruises leave from docks on the river or the lake, downtown (near the Riverwalk or Navy Pier). Best time: spring to autumn (cruises usually don't run in the depths of winter because of the cold and ice); sunset is especially lovely. Tips: book ahead in high season, choose an operator with a quality guide if architecture interests you, bring a light jacket (it's cooler on the water) and a charged camera. It's a perfect introduction to the city.
ℹ️ Distance: Leaves from river/lake docks downtown (near the Riverwalk or Navy Pier) · Best time: Spring to autumn (does not run in the depths of winter); sunset ideal · Admission: US$ 46-56 adult depending on the operator (Chicago Architecture Center US$ 55; Shoreline from US$ 46; 2025; check); book online · Duration: 1.5 hours
3
Art Institute of Chicago
One of the world's great art museums, with Impressionists, 'American Gothic' and 'Nighthawks'.
The Art Institute of Chicago is one of the most important and complete art museums in the United States and the world, and an essential visit. It occupies an imposing building in the heart of downtown, next to Millennium Park, guarded by two famous bronze lion statues at the entrance. Its collection spans thousands of years of art from every culture, but it shines especially for a handful of masterpieces that are universal icons. The museum has one of the best collections of Impressionist and Post-Impressionist painting outside France, with celebrated works by Monet (several of his haystack and Rouen Cathedral paintings), Renoir, Degas, Caillebotte ('Paris Street; Rainy Day') and the hugely famous 'A Sunday Afternoon on the Island of La Grande Jatte' by Georges Seurat, the great pointillist canvas. And it holds two of the most recognizable images in American art: Grant Wood's 'American Gothic' (the farmer and his daughter with the pitchfork) and Edward Hopper's 'Nighthawks' (the lonely night-time diner), so widely reproduced that they are recognized instantly. Beyond these stars, the museum covers early European art, modern and contemporary art, Asian art, armor, miniatures and much more, with a modern contemporary wing. It is a vast museum of the very highest quality. Getting there: downtown, next to Millennium Park; 'L' train to Loop stations. Best time: any day; midweek there are fewer people. Tips: the museum is big, so prioritize the masterpieces that interest you most (the Impressionists, American Gothic, Nighthawks); buy your ticket online; and it pairs perfectly with Millennium Park, right next door. There is usually a day or time slot with free or reduced admission (check).
ℹ️ Distance: Downtown, next to Millennium Park; 'L' train to the Loop · Best time: Midweek (fewer people) · Admission: US$ 32 adult non-Illinois resident (2025; Illinois residents and under-14s get discounts/free entry; check) · Duration: Half a day or more
4
Observation decks: Willis Tower (Skydeck) and 360 Chicago
The highest views in the city, with glass platforms over the void for the brave.
Chicago, birthplace of the skyscraper, offers some of the most spectacular observation decks in the United States, with views that on clear days reach several states and the immense Lake Michigan. There are two main ones, each with its own appeal. The Willis Tower (still known to many by its old name, Sears Tower) was for years the tallest building in the world and is still one of the tallest in the country. Its observation deck, the Skydeck, on the 103rd floor (about 412 meters up), offers a stunning panorama of the whole city and the lake. Its big draw is 'The Ledge', a set of balconies with completely transparent glass floors and walls that jut out from the building: standing on the glass, with the street more than four hundred meters below your feet, is a vertiginous experience and the most sought-after photo. The other great observation deck is 360 Chicago, at the top of the former John Hancock building, above the elegant Magnificent Mile. From its windows you see the city and the lake, and its adrenaline attraction is 'TILT', a platform whose windows tilt outward, leaving visitors 'hanging' over the avenue. It also has a bar up high. Getting there: the Willis Tower is in the west of the Loop; 360 Chicago is in the Magnificent Mile area (north). Best time: a clear day is essential for the views; sunset is magical (you see both day and night), though busier. Tips: buy timed tickets online to avoid queues, pick a day with no clouds or fog, and choose between them based on the view (the Willis, higher and to the south; the 360, over the lake and the Magnificent Mile). The glass platforms are not for anyone with a strong fear of heights.
ℹ️ Distance: Willis Tower in the west of the Loop; 360 Chicago on the Magnificent Mile (north) · Best time: Clear days; sunset (magical but busy) · Admission: Willis Tower Skydeck from US$ 32 adult / US$ 24 child; 360 Chicago from US$ 30 adult (TILT +US$ 14) (2025; check); buy online · Duration: 1 to 2 hours each
5
Navy Pier
Chicago's most famous pier on the lake, with its big Ferris wheel, promenades and entertainment.
Navy Pier is one of the most popular and most visited places in Chicago: a long pier reaching out into Lake Michigan, turned into a large complex of leisure, promenade and entertainment. Originally a cargo and recreation pier from the early 20th century, today it is a festive, family destination, especially lively in summer, with views of both the lake and the city skyline. Its symbol is the Centennial Wheel, a big Ferris wheel giving panoramic views of the lake and the city. The pier also brings together amusement rides for kids, restaurants, shops, gardens, theaters, an IMAX cinema and the Chicago Children's Museum, ideal for families. Many lake and river cruises leave from here too, including sightseeing trips and the architecture cruises. In summer there are fireworks displays over the lake on some nights. It is a very touristy and commercial area, but the walk along the pier, with the lake breeze and the skyline views, is very pleasant, and it makes a good plan for a relaxed afternoon, especially with children. Getting there: on the lake, east of downtown; by bus, taxi/app or a walk from downtown/the Magnificent Mile. Best time: summer, when it is in full swing; sunset for the views. Tips: it's ideal to combine with a cruise (many leave from here); the wheel and the rides are paid separately; in summer it can be very busy. Nice for families and for seeing the skyline from the lake.
ℹ️ Distance: On the lake, east of downtown; bus, taxi/app or on foot from the Magnificent Mile · Best time: Summer (in full swing); sunset for the views · Admission: Access to the pier free; Centennial Wheel US$ 19,50 adult; cruises and rides separate (2025; check) · Duration: Half a day (more with cruises)
6
The Riverwalk and downtown (the Loop)
The riverside promenade and the historic heart of Chicago, with its elevated train and skyscrapers.
Downtown Chicago, known as 'the Loop' (for the circuit the elevated train forms around it), is the historic and financial heart of the city, a forest of skyscrapers alongside architectural gems from every era. Walking it means admiring the birthplace of the skyscraper: buildings of the Chicago School, art deco, works by Mies van der Rohe and contemporary towers, plus public sculptures by artists such as Picasso, Miró and Calder scattered across the plazas. One of the city's great recent improvements is the Chicago Riverwalk, a lovely pedestrian promenade at water level along the bank of the Chicago River as it passes through downtown. Going down to the Riverwalk and walking beside the river, under the skyscrapers and the drawbridges, with cafés, bars and docks along the way, is a delightful urban experience, especially at sunset. It is one of the best places to feel the pulse of the city and have a drink with a view. The Loop is also home to lively State Street (with the historic Marshall Field's store, today Macy's), the Chicago Theatre with its famous illuminated sign, and the iconic elevated train ('L'), whose iron tracks running between the buildings are one of the most characteristic images of Chicago. Getting there: it is downtown itself; the 'L' train loops right around it. Best time: spring to autumn for the Riverwalk; any time for the Loop. Tips: combine an architectural walk around the Loop with some time on the Riverwalk at sunset; ride the elevated 'L' at least once for that very Chicago experience; and don't miss the public sculptures downtown. It's all walkable.
ℹ️ Distance: The city center (the Loop); the 'L' train loops around it · Best time: Spring to autumn for the Riverwalk; any time for the Loop · Admission: Free (walking is free); Riverwalk bars and cruises separate · Duration: Half a day
7
The Field Museum of Natural History and the Museum Campus
The museum of 'Sue', the most complete T. rex in the world, alongside the aquarium and the planetarium, facing the lake.
The Museum Campus is a green area on the shore of Lake Michigan, south of downtown, that brings together three of Chicago's great museums in a spectacular setting, with skyline views. It is an essential visit, especially for families and lovers of science and nature. The jewel is the Field Museum of Natural History, one of the largest natural history museums in the world. Its absolute star is 'Sue', the most complete and best-preserved Tyrannosaurus rex skeleton ever found, an impressive specimen. The museum also holds other dinosaurs, animal halls, gems, Egyptian mummies, a recreated tomb, and exhibitions about the cultures and peoples of the planet. It is enormous and fascinating. Next to the Field Museum are the Shedd Aquarium, one of the largest and most renowned aquariums in the country, with thousands of aquatic animals, from belugas and dolphins to coral reefs; and the Adler Planetarium, the first planetarium in the western hemisphere, with exhibitions about space and privileged skyline views from its position out into the lake. The whole campus, surrounded by lawns and waterside paths, makes a perfect day out. Getting there: south of downtown, beside the lake; by bus, taxi/app or a walk from downtown. Best time: any day; midweek there are fewer people. Tips: each museum charges separately (there are combos and city passes that may be worth it if you visit several); choose according to your interests (the Field for dinosaurs, the Shedd for marine life, the Adler for space); and make the most of the skyline views from the Museum Campus, among the best in the city.
ℹ️ Distance: South of downtown, beside the lake (Museum Campus); bus, taxi/app or on foot · Best time: Midweek (fewer people) · Admission: Field Museum from US$ 30 adult non-resident; Shedd Aquarium US$ 39,95 adult non-resident; Adler Planetarium US$ 25-38; combos/CityPASS available (2025; check) · Duration: Half a day to a day (depending how many museums)
8
The Magnificent Mile and the Gold Coast
Chicago's great shopping avenue and the elegant residential neighborhoods beside the lake.
The Magnificent Mile is Chicago's most famous and elegant avenue for shopping and strolling: a stretch of North Michigan Avenue, north of the river, packed with luxury stores, department stores, vertical malls, hotels and restaurants. It is Chicago's equivalent of the world's great shopping avenues, lively and eye-catching, especially pretty at Christmas, when it is decorated and lit up. Along the avenue and around it there are also architectural landmarks. The most curious and best loved is the historic Chicago Water Tower, a small neo-Gothic stone tower that was one of the few buildings to survive the Great Fire of 1871, today a symbol of the city's resilience. Nearby is the former John Hancock building, with the 360 Chicago observation deck at the top. North of the Magnificent Mile lies the Gold Coast, one of Chicago's most elegant and expensive neighborhoods, beside the lake: tree-lined streets with historic mansions, stately buildings and a distinguished residential feel, very pleasant for a stroll. From there you reach the lake's urban beaches (like Oak Street Beach), where in summer Chicagoans sunbathe with the skyline as a backdrop. Getting there: north of the river; 'L' train to nearby stations, bus or on foot from downtown. Best time: any day for shopping; especially lovely at Christmas; summer to combine with the lake beaches. Tips: combine shopping with a walk around the Gold Coast and, in summer, some time on the urban beach; remember that prices are shown without tax; and take the chance to go up to the 360 Chicago deck, which is right on the avenue.
ℹ️ Distance: North Michigan Avenue, north of the river; 'L' train, bus or on foot · Best time: Any day; lovely at Christmas; summer for the lake beaches · Admission: The stroll is free; shopping depends on your budget. Tax is added to the price · Duration: Half a day
9
Neighborhoods with character: Wicker Park, Pilsen and Chinatown
The most authentic and diverse Chicago, with art, murals, ethnic food and neighborhood life outside downtown.
Beyond the skyline and the big museums, Chicago is a city of neighborhoods with enormous personality, where you feel the most authentic and diverse pulse of the metropolis. Exploring them is discovering another side of the city, full of art, immigrant culture, food and local life. Wicker Park and neighboring Bucktown are the fashionable, young, creative neighborhoods: former working-class immigrant districts (mainly Polish) now turned into the city's 'hipster' epicenter, with design boutiques, record and vintage clothing shops, specialty coffee bars, bars, restaurants and a lively music and nightlife scene. It's ideal for wandering, eating well and soaking up Chicago's alternative vibe. Pilsen is the heart of Chicago's Mexican community, a vibrant, colorful neighborhood famous for its Chicano murals covering the walls, its Mexican taquerías and bakeries, its galleries and the National Museum of Mexican Art (free and excellent). It is a neighborhood with huge identity and Latin flavor. And Chinatown, south of downtown, offers its traditional gate, its dim sum restaurants, its shops and its atmosphere, one of the most authentic Chinatowns in the country. Each neighborhood is almost a city in itself, a reflection of the enormous migrant diversity that built Chicago. Getting there: by 'L' train (each neighborhood has its own lines/stations) or taxi/app. Best time: any day during the day for wandering; evenings for the Wicker Park bars. Tips: give an afternoon to whichever neighborhood appeals most; in Pilsen, walk the murals and eat authentic tacos (and visit the Mexican art museum, free); in Chinatown, try the dim sum. It's the best way to get to know the real Chicago beyond downtown.
ℹ️ Distance: Outside downtown; 'L' train (lines depending on the neighborhood) or taxi/app · Best time: Daytime for wandering; evenings for the Wicker Park bars · Admission: Free (wandering the neighborhoods is free); the Mexican art museum in Pilsen is free; food separate · Duration: Half a day per neighborhood
10
Baseball at Wrigley Field and a night of blues and jazz
The historic Cubs ballpark and the legendary music scene that made Chicago the capital of the blues.
Chicago lives sport and music with a passion that is part of its identity, and experiencing either is unforgettable. On the sporting side, the great temple is Wrigley Field, home of the Chicago Cubs (baseball), opened in 1914 and the second oldest ballpark in the Major Leagues. With ivy climbing the outfield walls, its old manual scoreboard and its neighborhood atmosphere (lively Wrigleyville surrounds it, full of bars), it is one of the most charming stadiums in the country. Going to a Cubs game, even if you don't understand baseball, is diving into the soul of Chicago. The city also has other legendary teams: the White Sox (baseball), the Bears (American football) and, above all, the Bulls in basketball, Michael Jordan's team in the mythical 1990s. Musically, Chicago is nothing less than the birthplace of electric blues. When African Americans from the South migrated to the city in the first half of the 20th century (the Great Migration), they brought the blues with them, and here it was electrified and gave rise to the sound that would influence all the rock that followed; legendary figures such as Muddy Waters defined it. Today, the city keeps an extraordinary live blues and jazz scene: in the blues clubs you can hear live music every night, an essential experience. Summer also brings big free blues and jazz festivals. Getting there: Wrigley Field is to the north ('L' red line to Addison); the blues clubs are spread around the city (taxi/app). Best time: baseball season (spring to autumn) for a game; music all year; summer for the free festivals. Tips: buy game tickets through official channels; for the blues clubs, pick one with a good reputation and check the lineup; and make the most of the summer festivals if they coincide with your trip.
ℹ️ Distance: Wrigley Field to the north ('L' red line, Addison); blues clubs spread around (taxi/app) · Best time: Baseball season for a game; music all year; summer for the free festivals · Admission: Cubs game from US$ 20-60 (depending on opponent/seat); blues club cover US$ 10-20; summer festivals free (2025; check) · Duration: An afternoon/evening each
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What nobody tells you

💵 Prices

Tickets

TypePrice
Millennium Park (Cloud Gate / the Bean)Free (open access); winter skating separate (US$ 15-19 with skate rental)
Architecture cruise on the riverUS$ 46-56 adult depending on the operator (Chicago Architecture Center US$ 55; Shoreline/Wendella from US$ 46; 2025; check); book online
Art Institute of ChicagoUS$ 32 adult non-Illinois resident (2025; Illinois residents and under-14s get discounts/free entry; check)
Willis Tower Skydeck (The Ledge)From US$ 32 adult / US$ 24 child 3-11 (2025; check); buy online
360 Chicago (TILT)From US$ 30 adult / US$ 20 child; TILT +US$ 14 (2025; check); buy online
Navy Pier (access)Free; Centennial Wheel US$ 19,50 adult; rides and cruises separate (2025; check)
Field Museum (Sue, the T. rex)From US$ 30 adult non-resident; less for Illinois residents; free Wednesdays for Illinois residents (2025; check)
Shedd AquariumUS$ 39,95 adult non-resident, US$ 29,95 child 3-11; US$ 19,95 adult Chicago resident (2025; check)
Adler PlanetariumUS$ 25-38 adult depending on the package (2025; check)
National Museum of Mexican Art (Pilsen)Free (open access)
Cubs game at Wrigley Field (MLB)US$ 20-60+ depending on the opponent and seat (2025; official channels)
Live blues and jazz clubsCover US$ 10-20 (plus a drink); summer festivals free (2025; check)
🔄 updated monthlyOfficial / reference values · double-check when buying

Activities and tours

ActivityPriceDurationOperator
Architecture cruise on the Chicago RiverUS$ 46-56 adult (2025)1.5 hChicago Architecture Center, Shoreline, Wendella
Architecture walking tour of the LoopUS$ 30-40 pp (2025)2 hChicago Architecture Center and guides
Cubs game (MLB) at Wrigley Field or Bulls game (NBA)Cubs from US$ 20-60+; Bulls from US$ 30-100+ (2025)An afternoon/eveningOfficial ticket channels (MLB/NBA)
A night of live blues or jazzCover US$ 10-20 plus a drink (2025)An eveningBuddy Guy's Legends, Kingston Mines and other clubs
Food tour (deep dish pizza, hot dog, etc.)US$ 60-90 pp with tastings (2025)2-3 hFood tour operators (Chicago Food Planet, etc.)
Tour of the murals and food of PilsenUS$ 40-70 pp (2025)2-3 hLocal guides and agencies
A day cycling along the lake (Lakefront Trail)Divvy: US$ 18,10 day pass (Divvy 2025)Half a dayDivvy (bike share) and rental shops
Trip to Frank Lloyd Wright's house (Oak Park)Home & Studio Tour US$ 25-30 adult (2025)Half a dayFrank Lloyd Wright Trust
🔄 updated monthlyOfficial / reference values · double-check when buying
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🚌 How to get there and distances

Getting around

ModePriceDurationNotes
The 'L' train (CTA, elevated and underground metro)US$ 2,75 per ride; day pass US$ 6; 7-day pass US$ 25 (the 3-day pass was discontinued in 2026). From O'Hare, a special fare of US$ 5 (source: CTA transitchicago.com/fares, verified July 2026)VariableChicago's iconic elevated train, with color-coded lines that loop around the Loop and connect the whole city and both airports (Blue Line to O'Hare 24 h, Orange Line to Midway). HOW TO PAY: with a Ventra card (rechargeable, from station machines), or by tapping a contactless credit/debit card or your phone with the Ventra Card loaded into Apple Pay / Google Pay directly on the reader. To check timetables and see the train in real time, people use the Ventra app, the Transit app or Google Maps
City bus (CTA Bus)US$ 2,50 per ride; same Ventra card or contactless tap (source: CTA, verified July 2026)VariableA wide network that complements the train and reaches areas with no 'L' station, such as Navy Pier or the Museum Campus. Pay with Ventra, a contactless card or your phone; transfers with Ventra cost only US$ 0,25 within 2 hours. Real-time tracking with the Transit or Ventra app
Commuter train (Metra)US$ 3,75-6,75 depending on zones; day pass US$ 14 (Metra 2025; check)VariableConnects downtown with the suburbs and day-trip destinations (such as Oak Park, for Frank Lloyd Wright). Departs from stations like Union Station and Ogilvie
Taxi and apps (Uber, Lyft)City ride US$ 12-25; to the airport US$ 40-60 (2025)VariableHandy for one-off trips, at night or for poorly connected areas. Widely used in the city
Bike share (Divvy) and walkingDivvy: day pass US$ 18,10; walking is free (2025)VariableDowntown is very walkable. Divvy is the bike-share system, ideal for riding the lovely Lakefront Trail beside Lake Michigan
Walking downtown (the Loop) and the RiverwalkFreeVariableDowntown Chicago is compact and very walkable; the Riverwalk and the lakefront paths are the best way to explore it and enjoy the architecture
🔄 updated monthlyOfficial / reference values · double-check when buying

How to get there

RouteAirlines / operatorsAvg. priceDuration
O'Hare Airport (ORD) → downtown ('L' train)CTA Blue Line (station at the airport, 24 h) to the LoopUS$ 5 from O'Hare (special fare; source: CTA, verified July 2026)45 min to 1 h
O'Hare Airport (ORD) → downtown (taxi or app)Taxis and apps (Uber, Lyft)US$ 45-65 depending on traffic (2025)30 min to 1 h depending on traffic
Midway Airport (MDW) → downtownCTA orange line, taxi or appCTA train US$ 2,75; taxi/app US$ 30-45 (2025)30 to 45 min
Arriving by train (Union Station)Amtrak (national routes and to other Midwest cities)From Detroit US$ 35-65; from St. Louis US$ 30-55 (2025; depending on the date)Depends on origin
Arriving by long-distance busFlixBus, Greyhound, MegabusFrom Midwest cities US$ 15-50 (2025; depending on origin)Depends on origin
🔄 updated monthlyOfficial / reference values · double-check when buying

🏨 Where to stay

No exact prices: a scale from $ (budget) to $$$$$ (luxury), with 2-3 options per category.

CategoryPriceRecommended options
Luxury / iconic (Magnificent Mile, beside the lake)$$$$$US$ 300-600 a night; grand luxury hotels on the Magnificent Mile, in the Gold Coast and beside the lake, such as The Peninsula, Four Seasons or The Langham, some in skyscrapers with spectacular views (2025; check)
Mid-range downtown (the Loop) and River North$$$$$US$ 150-280 a night; a good choice of mid-range hotels in the Loop and River North (Hampton Inn, Hyatt, Kimpton), very well connected by the 'L' train and steps from the attractions (2025; check)
Characterful and boutique (River North, Wicker Park)$$$$$US$ 200-350 a night; boutique hotels with character in River North or near Wicker Park (The Robey, Ace Hotel), with good food and neighborhood life (2025; check)
Budget / hostels (near the 'L')$$$$$US$ 40-70 a bed in a hostel (HI Chicago, Freehand); budget hotels US$ 100-150 a night in areas well connected by the 'L' train (2025; check)

🍴 Where to eat

TypePriceOptions / signature dish
Chicago-style pizza (deep dish)$$$$$US$ 18-35 a pizza (2-3 people); the deep-pan pizza, thick and filled with cheese and sauce. Classics like Lou Malnati's, Giordano's and Pizzeria Uno
Chicago-style hot dog and street food$$$$$US$ 4-10 each; the Chicago-style hot dog (never with ketchup, according to tradition) and the Italian beef sandwich. Portillo's, The Wieners Circle, Al's Beef
Pilsen's Mexican cooking and Latin food$$$$$US$ 8-20 per person; some of the best Mexican taquerías and bakeries in the country in Pilsen and La Villita; authentic and cheap
Fine dining and award-winning restaurants$$$$$US$ 100-400+ per person (tasting menus); a top-tier scene with restaurants such as Alinea, Oriole or Smyth (several Michelin stars). Book well in advance
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📖 History of Chicago

Origins, formation and what the sources say.

The origin of the name and the Indigenous peoples

The name 'Chicago' has its roots in the languages of the region's Indigenous peoples. It comes from a word in the Miami-Illinois language, usually transcribed as 'shikaakwa', which referred to a wild plant of the onion or garlic family (sometimes translated as 'wild onion', 'wild leek' or 'skunk', because of its pungent smell), which grew in abundance in the marshy, damp ground beside the lake and the river. That humble name tied to a swamp plant ended up christening one of the world's great metropolises.

Before the Europeans arrived, the region of present-day Chicago was inhabited by Algonquian-speaking peoples. At different times, nations of the Illinois Confederation lived there and, later, the Potawatomi, along with other peoples. They lived by hunting, fishing, gathering and farming, making the most of a rich area where the Chicago River flowed into the immense Lake Michigan.

The location was extraordinarily strategic, something the Indigenous peoples knew well and which would prove decisive in the city's history: very close by, a short stretch of land (a 'portage') separated the Great Lakes basin from that of the Mississippi River. Whoever controlled that point controlled one of the great natural crossroads of the continent, linking the Atlantic east with the heart of the continent and, downriver, with the Gulf of Mexico. That privileged geography would be the key to Chicago's destiny.

The meaning of 'shikaakwa'
Linguists connect the place name 'Chicago' to the Miami-Illinois word 'shikaakwa', referring to a strong-smelling wild plant of the onion/garlic family (or, in some interpretations, to the skunk). There are nuances between the translations ('wild onion', 'wild leek'), so it should be taken as an approximation.
Source: https://en.wikipedia.org/wiki/Chicago
The Chicago Portage
Historians stress the geographical importance of the 'Chicago Portage', the short stretch of land connecting the Great Lakes basin with that of the Mississippi, known and used by the Indigenous peoples and the French explorers, and key to understanding why the city became a great transport hub.
Source: https://en.wikipedia.org/wiki/Chicago_Portage

Du Sable, the first settler, and the city's incorporation (1837)

The story of the first permanent non-Indigenous settlement in Chicago has a remarkable and often overlooked protagonist: Jean Baptiste Point du Sable, a fur trader of African descent, connected to Haiti and to French heritage. Toward the end of the 18th century (in the 1780s), Du Sable established a thriving trading post and his home at the mouth of the Chicago River, becoming the first permanent settler in the place. Today he is officially recognized as the founder of the city, a significant fact: the great metropolis of the Midwest was founded by a Black man.

In the early 19th century, the US Army built Fort Dearborn there, and a small settlement began to grow around the fort and the trade. The place stayed modest for decades, but its strategic position at the crossroads of the continent's great waterways drew more and more interest. The signing of treaties with the Indigenous peoples (which meant their displacement from the region) opened the way to mass settlement.

In 1833, the settlement was organized as a small 'town' with barely a few hundred inhabitants. And growth was so dizzying that only four years later, in 1837, Chicago was officially incorporated as a city, already with several thousand inhabitants. What followed would be one of the fastest and most spectacular episodes of urban growth in history: within a few decades, that swampy settlement would become one of the world's great cities.

Du Sable, Chicago's founder of African descent
Jean Baptiste Point du Sable, a trader of Afro-Haitian origin and French heritage, is recognized as the first permanent non-Indigenous settler and founder of Chicago, established at the mouth of the river around the 1780s. His figure is today claimed as a foundational part of the city's identity.
Source: https://en.wikipedia.org/wiki/Jean_Baptiste_Point_du_Sable

Railroads, grain and the great growth (19th century)

Chicago's growth in the 19th century was, quite simply, explosive, and it came from its role as the great transport hub of the center of the continent. First came water: the opening of the Illinois and Michigan Canal in 1848 finally connected the Great Lakes to the Mississippi River system by navigable water, exactly what the geography had promised. But the real engine was the railroad: Chicago became the largest rail hub in the United States, the point where the lines linking the industrialized east with the vast agricultural and ranching west converged.

That position turned it into the great market and processing center for the riches of the Midwest. Chicago became the world capital of grain (with its enormous silos and its commodities exchange), of timber and, above all, of meat: its gigantic slaughterhouses and packing plants (the famous Union Stock Yards) processed livestock from across the west and distributed it around the country in the new refrigerated cars. The city drew hundreds of thousands of European immigrants —Germans, Irish, Poles, Italians, Scandinavians and many more— who came to work in its industries, factories and slaughterhouses.

Within a few decades, Chicago went from a few thousand inhabitants to being one of the biggest and most dynamic cities in the country, a thriving, industrial, cosmopolitan metropolis that symbolized the energy and ambition of the young, expanding nation. It was a city growing at a dizzying, almost chaotic speed, on the marshy ground beside the lake.

Chicago, hub of the Midwest
Economic historians (such as William Cronon in 'Nature's Metropolis') explain Chicago's rise through its role as the great intermediary between the agricultural/ranching west and the industrial east, thanks to its unmatched rail network and its grain, timber and meat markets, which made it the economic heart of the Midwest.
Source: https://en.wikipedia.org/wiki/History_of_Chicago

The Great Fire of 1871 and the birth of the skyscraper

The most dramatic event in Chicago's history, and at the same time the origin of its architectural glory, was the Great Fire of 1871. In October of that year, a fire broke out in the city (popular legend, with no solid basis, blamed a cow that was said to have knocked over a lantern in a barn) and, fed by the wind and by a city built largely of wood after years of disorderly growth, it burned for days. The fire razed much of downtown, left tens of thousands of people homeless and killed hundreds. It was a catastrophe of colossal proportions.

But Chicago turned the tragedy into an extraordinary opportunity. Rebuilding the city almost from scratch drew a generation of brilliant, daring architects who, with new techniques and new materials (steel frames, elevators, fireproof concrete), revolutionized the way things were built. Out of that ferment came the so-called Chicago School of architecture and, with it, an invention that would change cities across the world: the skyscraper. Chicago put up the first tall buildings with steel frames, freed from thick load-bearing walls.

That innovative tradition continued throughout the following century, with figures such as Louis Sullivan, Frank Lloyd Wright and, later, Mies van der Rohe, making Chicago one of the world capitals of architecture, a role it holds to this day. The splendor of the rebuilt city was dazzlingly displayed in 1893, when Chicago hosted the World's Columbian Exposition, a magnificent world's fair that showed the world the city's rebirth.

The legend of Mrs. O'Leary's cow
The popular explanation that the Great Fire of 1871 started because Mrs. O'Leary's cow knocked over a lantern has no evidence behind it and is considered a legend (indeed one that unfairly pinned the blame on an immigrant family). The exact origin of the fire was never determined with certainty.
Source: https://en.wikipedia.org/wiki/Great_Chicago_Fire
Chicago, birthplace of the skyscraper
Architectural historians place the birth of the modern skyscraper and of the 'Chicago School' in the Chicago that followed the 1871 fire, thanks to the pioneering use of steel frames, elevators and new techniques. The debate over which was 'the first skyscraper' continues, but Chicago's foundational role is undisputed.
Source: https://en.wikipedia.org/wiki/Chicago_school_(architecture)

The Great Migration, the blues and the gangster era (20th century)

The 20th century brought Chicago new waves of people and new memorable chapters. One of the most profound was the Great Migration: from the First World War onward, and through the following decades, hundreds of thousands of African Americans from the rural South migrated to Chicago (as to other northern cities) fleeing segregation and poverty, in search of work in industry. That migration transformed the city's demographics and culture, and had an extraordinary artistic consequence: Black musicians from Mississippi brought the blues with them, and in Chicago it was 'electrified' (with the electric guitar and a full band) and gave rise to the famous Chicago blues, embodied by legendary figures such as Muddy Waters, which would decisively influence the birth of rock and roll.

The other great image of the Chicago of that era is darker and more cinematic: the Prohibition years (the ban on alcohol, in the 1920s). Prohibition set off bootlegging and organized crime, and Chicago became the setting par excellence for gang wars. The mythic figure of those years is Al Capone, the famous mobster who controlled much of the city's illegal business, in an era of shootouts, bribes and famous episodes like the St. Valentine's Day Massacre of 1929. That gangster image marked the popular imagination about Chicago forever.

Beyond the dark legend, 20th-century Chicago consolidated itself as a thriving industrial, financial and cultural metropolis, with great institutions, universities, museums and a rich artistic life, the undisputed capital of the American Midwest.

Chicago blues and the Great Migration
Musicologists link the birth of 'Chicago blues' (electric blues) to the arrival of African American musicians from the South during the Great Migration of the 20th century. Figures such as Muddy Waters turned the acoustic Delta blues into an electric band sound that would be fundamental to the rock that followed.
Source: https://en.wikipedia.org/wiki/Chicago_blues
Al Capone and the gangster myth
The Prohibition era (the 1920s) made Chicago a byword for organized crime, with Al Capone as its emblematic figure. Although there is a great deal of legend and cinematic mythmaking, the boom in alcohol smuggling and the gang wars of those years are historical facts.
Source: https://en.wikipedia.org/wiki/Al_Capone

Capital of architecture and modern metropolis

In the second half of the 20th century and into the 21st, Chicago consolidated its identity as one of the world's great capitals of architecture and as a modern, cultured, vibrant metropolis. The tradition begun after the 1871 fire continued with the arrival of the architect Mies van der Rohe, a master of the modern movement, whose steel and glass towers defined much of the skyline and of 20th-century architecture. Later, Chicago went on putting up ever taller skyscrapers, such as the Willis Tower (formerly the Sears Tower), for years the tallest building in the world. Today a cruise along its river is a tour through the best architecture of the last hundred and fifty years.

The city also renewed its Lake Michigan waterfront, one of its greatest treasures, with kilometers of parks, urban beaches and publicly accessible promenades (a vision inherited from Daniel Burnham's city plan, which sought to preserve the shore for the people). The great symbol of that renewal is Millennium Park, opened in 2004, with its famous mirrored sculpture Cloud Gate (the 'Bean'), which became the city's new icon. The Riverwalk, along the river, completed that transformation of public space.

Chicago today is the third city of the United States, an important financial center (with one of the world's largest futures exchanges), transport hub (its O'Hare airport is among the busiest on the planet), and educational and cultural center. It keeps its hard-working, warm Midwestern character, its architectural pride, its passion for sport and music, and an identity of its own that sets it apart from the coastal metropolises. Out of that swampy 'wild onion' settlement grew one of the great cities of the world.

The legacy of preserving the lakefront
Public access to the shore of Lake Michigan, today one of Chicago's great attractions, is largely credited to the vision of the planner Daniel Burnham and his 1909 'Plan of Chicago', which argued for keeping the shoreline open to citizens rather than privatizing it, a decision of enormous long-term value.
Source: https://en.wikipedia.org/wiki/Burnham_Plan_of_Chicago

📚 Bibliography

  • Wikipedia (ES) — «Chicago»: https://es.wikipedia.org/wiki/Chicago
  • Wikipedia (EN) — «Chicago»: https://en.wikipedia.org/wiki/Chicago
  • Wikipedia (EN) — «History of Chicago»: https://en.wikipedia.org/wiki/History_of_Chicago
  • Wikipedia (EN) — «Jean Baptiste Point du Sable»: https://en.wikipedia.org/wiki/Jean_Baptiste_Point_du_Sable
  • Wikipedia (EN) — «Great Chicago Fire»: https://en.wikipedia.org/wiki/Great_Chicago_Fire
  • Wikipedia (EN) — «Chicago school (architecture)»: https://en.wikipedia.org/wiki/Chicago_school_(architecture)
  • Wikipedia (EN) — «World's Columbian Exposition»: https://en.wikipedia.org/wiki/World%27s_Columbian_Exposition
  • Wikipedia (EN) — «Chicago blues»: https://en.wikipedia.org/wiki/Chicago_blues
  • Wikipedia (EN) — «Al Capone»: https://en.wikipedia.org/wiki/Al_Capone
  • Wikipedia (EN) — «Burnham Plan of Chicago»: https://en.wikipedia.org/wiki/Burnham_Plan_of_Chicago
  • Chicago Architecture Center: https://www.architecture.org/

❓ Frequently asked questions

When is the best time to visit Chicago?+
Summer (June to August) is the best and liveliest time: warm weather, festivals, beaches on the lake, terraces and outdoor life (it is high season). Late spring (May) and autumn (September-October) offer pleasant weather and fewer people. Winter is very cold, windy and snowy —Chicago is famous for its harsh winters beside the lake—, with Christmas charm but tough conditions.
Why is it called the 'Windy City'?+
Chicago is known as the 'Windy City', and although it is usually put down to the wind blowing off Lake Michigan (which is real enough), many historians believe the nickname actually came from the reputation of its politicians and boosters for being 'full of wind' — big talkers and braggarts — especially around the time of the 1893 Exposition. Both explanations coexist; what is certain is that it can be very windy beside the lake, above all in winter.
How many days do I need?+
Two to three days covers the essentials: Millennium Park and the Bean, an architecture cruise, an observation deck, the Art Institute, Navy Pier and the Riverwalk. With four to five days you add more museums (the Field, the Shedd, the Adler), neighborhoods like Wicker Park or Pilsen, a game or a night of blues, and time to enjoy the lake. Chicago tends to be a pleasant surprise and rewards several days.
How do I get around Chicago and how do I pay for transport?+
The 'L' train (the CTA, partly elevated and partly underground) is the best option: fast, connecting the whole city and both airports, and an experience in itself (US$ 2,75 a ride; day pass US$ 6, 7-day pass US$ 25). There are three ways to pay: buy a rechargeable Ventra card from the station machines, or tap a contactless credit/debit card directly on the reader, or use your phone with the Ventra Card in Apple Pay or Google Pay. To see the train or bus in real time, download the Ventra app or the Transit app (Google Maps works too). There are also CTA buses, Metra commuter trains for day trips (Oak Park, etc.), taxis and apps. Downtown and the lakefront are very easy to cover on foot and on Divvy bike share. Verified July 2026.
Is the architecture cruise worth it?+
Absolutely. For many it is the best activity in Chicago: a boat ride along the river taking in the skyscrapers, with a guide telling the story of the birthplace of modern architecture. It lasts about an hour and a half and gives a unique perspective on the city. It's worth booking ahead in summer and choosing an operator with good guides (such as the Chicago Architecture Center).
Do I need a visa or authorization to enter the United States?+
It depends on your nationality. Many countries use the ESTA electronic authorization (Visa Waiver Program); others, such as Argentina, require a tourist visa (B2), applied for at the embassy or consulate in advance. Always check the current requirements for your passport before traveling; this guide does not replace official information.
Is Chicago safe for tourists?+
The tourist areas (downtown/the Loop, the Magnificent Mile, the Gold Coast, the lakefront, the fashionable neighborhoods) are safe and very busy. Chicago has a reputation for crime in certain outlying neighborhoods, but those are not the areas tourists visit. As always, common sense helps: look after your belongings, travel by taxi/app at night and don't venture into distant neighborhoods without information. The usual areas can be enjoyed without worry.
Sources consulted (23)
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Image credits
Photos from Wikimedia Commons, each under its own licence (CC BY, CC BY-SA or public domain). Open each file to see its author and licence.
Chicago River ferry b