Illinois · United States
The city that invented the skyscraper, rebuilt itself after burning down, and put 42 kilometres of public beach on a freshwater sea.
In October 1871 a fire destroyed about nine square kilometres of Chicago and left a third of the population homeless. The rebuilding that followed produced, within fifteen years, the first steel-framed skyscraper in the world, and the city has been arguing about buildings ever since. Louis Sullivan, Frank Lloyd Wright, Mies van der Rohe and Frank Gehry all worked here, and the result is the most architecturally serious city in the United States.
It sits on Lake Michigan, which is 494 kilometres long and behaves like a sea — it has waves, storms and a horizon. An unusual 19th-century decision kept almost the entire waterfront in public hands, so Chicago has 42 kilometres of lakefront parks, beaches and a continuous cycling path where most cities would have private development and a motorway.
The third thing is the music. The Great Migration brought hundreds of thousands of Black Americans north from the Mississippi Delta between the 1910s and 1970s, and the blues they brought was electrified here, in South and West Side clubs, and became the direct ancestor of rock and roll. Chess Records was a mile from the Loop. That lineage is still audible in clubs across the city most nights of the week.
Why visit
Chicago is consistently under-visited by international travellers relative to its quality, and it is a considerably better city than its reputation abroad suggests.
The skyscraper was invented here in 1885. The Loop holds work by Sullivan, Burnham, Mies van der Rohe and Jeanne Gang within a few blocks, and Frank Lloyd Wright's home, studio and 25 of his buildings are in Oak Park, half an hour away.
The second-largest art museum in the United States, with a French Impressionist collection second only to Paris — Seurat's La Grande Jatte, Caillebotte's Paris Street, six Monet haystacks — plus Hopper's Nighthawks and Wood's American Gothic.
Parks, beaches and a continuous walking and cycling trail along the entire city shoreline, kept public by a 19th-century campaign. In summer Chicago has genuine city beaches on freshwater.
Muddy Waters, Howlin' Wolf and Buddy Guy all recorded in this city, and the clubs that carry that tradition still run live music most nights, on the South and West Sides and in the North Side venues.
Hotels, restaurants and drinks run 25–40% below New York or San Francisco for equivalent quality, and the food scene is one of the strongest in the country.
Main attractions
The Loop and the lakefront cover most of it, and both are walkable. The neighbourhoods need the L train.
Ninety minutes on the Chicago River through the heart of the Loop with a trained docent explaining the buildings on both banks. It is the single best introduction to any American city and there is no close competitor.
Tip The Chicago Architecture Center's own tours have the best-trained guides. Book ahead in summer and sit on the open upper deck.
Two million square feet of galleries holding Seurat's A Sunday on La Grande Jatte, Hopper's Nighthawks, Grant Wood's American Gothic, and one of the great Impressionist collections outside France. The Thorne Miniature Rooms are an unexpected delight.
Tip Enter through the Modern Wing on Monroe Street rather than the lion entrance — it is quieter and better organised.
A park built over a railway yard, holding Anish Kapoor's mirrored Cloud Gate — universally called the Bean — Frank Gehry's Pritzker Pavilion, and the Crown Fountain's video faces that spout water at children in summer.
Tip The Bean at dawn, with the skyline reflected and nobody in the frame, is worth the early start.
The Rookery with Frank Lloyd Wright's light court, the Monadnock's load-bearing brick walls, the Chicago Board of Trade, and Mies van der Rohe's Federal Center. Most are free to walk into the lobbies.
Tip The Chicago Architecture Center runs excellent walking tours of the Loop. The Rookery lobby alone is worth ten minutes.
Forty-two kilometres of path along Lake Michigan from the far north to the far south side, passing Oak Street and North Avenue beaches, Navy Pier and the Museum Campus.
Tip The stretch from the Museum Campus north to Lincoln Park is the classic ride, with the skyline on one side and the lake on the other.
The Field Museum of natural history with Sue the Tyrannosaurus, the Shedd Aquarium and the Adler Planetarium, on a lakefront peninsula south of the Loop. The view of the skyline from the Adler's point is the best in the city.
Tip Walk out to the Adler even if you skip the planetarium. The skyline view from there is the classic Chicago photograph.
Half an hour west on the Green Line, holding Wright's own home and studio plus 25 buildings from his Prairie School years, the largest concentration of his work anywhere.
Tip The home and studio tour is the essential one and sells out. The Unity Temple nearby is his masterpiece of the period.
Wicker Park and Logan Square for bars and restaurants, Pilsen for Mexican food and murals, Chinatown for one of the largest in the country, Hyde Park for the university and Obama's old neighbourhood.
Tip Pilsen's 16th Street murals and the National Museum of Mexican Art, which is free, are both underrated.
Things to do
Chicago rewards a mix of the Loop, the lake and one neighbourhood a day.
Do this on your first afternoon. Ninety minutes on the river gives you the city's history, geography and buildings in one go, and everything you see afterwards makes more sense.
Tip Late afternoon light on the buildings is best. Several operators run it — the Chicago Architecture Center's is the most substantive.
Forty-two kilometres of separated path along Lake Michigan. The stretch from the Museum Campus north past the beaches to Lincoln Park is about 10 km and is the best free thing in the city.
Tip Divvy bike-share docks are everywhere along the route. Go early — it is busy with runners and cyclists by 08:00 in summer.
Chicago blues is electrified Delta blues and the city's clubs still play it seven nights a week. The North Side venues are easiest to reach; the South and West Side clubs are closer to the source.
Tip Buddy Guy's Legends downtown is the famous one. Ask locally about the smaller South Side rooms if you want the real thing.
Deep-dish is the famous one and locals eat it rarely. Tavern-style thin crust cut into squares is what Chicago actually eats. The Italian beef sandwich — thin sliced beef, gravy, hot giardiniera — is the true local dish.
Tip Order the beef 'dipped, hot' and eat it leaning forward. Deep-dish takes 45 minutes to bake — order when you sit down.
The elevated railway that gives the downtown its name runs on tracks above the street, through the middle of the buildings. The Brown or Pink line circuit costs one fare and is a genuine sightseeing ride.
Tip Sit at the front of the first carriage. The stretch around the northeast corner of the Loop is the best.
Willis Tower's Skydeck has glass boxes projecting from the 103rd floor; 360 Chicago at the John Hancock has a tilting window and, crucially, a view that includes the Willis Tower.
Tip 360 Chicago has the better view because Willis is in it. The Signature Lounge one floor up charges nothing but the price of a drink.
Local food
Chicago is one of America's great eating cities and its reputation abroad rests on the wrong dish. Deep-dish is real; it is not what people here eat most weeks.
Thin-sliced slow-roasted beef in seasoned gravy on a French roll, with sweet peppers or spicy pickled giardiniera. Ordered 'dipped' means the whole roll goes into the gravy. This, not deep-dish, is the genuine Chicago sandwich.
Where to try it Beef stands across the city, most of them counter-service and unglamorous. Ask for it dipped and hot.
Deep-dish is a buttery high-sided crust filled with cheese, toppings and chunky tomato on top, baked for 45 minutes. Tavern-style is thin, crisp and cut into squares — and is what Chicagoans actually order.
Where to try it Deep-dish downtown; tavern-style at neighbourhood bars across the North and Southwest sides.
An all-beef frankfurter in a poppy-seed bun with mustard, onion, relish, tomato, a pickle spear, sport peppers and celery salt. Never ketchup — the prohibition is genuine and enforced socially.
Where to try it Hot dog stands everywhere. Ask for it 'dragged through the garden' for all the toppings.
Chicago has one of the largest Mexican populations in the United States, and the taquerías, bakeries and torta shops of Pilsen and Little Village are the everyday result.
Where to try it 18th Street in Pilsen and 26th Street in Little Village. Birria and al pastor are the specialities.
Chicago has the largest Polish population outside Poland, and pierogi, kielbasa and Polish bakeries are a genuine part of the city's food landscape, mostly on the northwest side.
Where to try it Avondale, Jefferson Park and Archer Heights. Milk bars and delis rather than restaurants.
Chicago has been one of the most innovative restaurant cities in the world for two decades, with a cluster of tasting-menu restaurants that reshaped American cooking. Reservations open months ahead.
Where to try it West Loop and Fulton Market hold most of them. Book the day reservations open.
Accommodation
The Loop and River North are central and convenient; the neighbourhoods north and west are cheaper and considerably more interesting in the evening.
Transport
Chicago is the transport hub of the American interior, with two airports and the country's busiest rail junction.
The L train and walking cover almost everything. Chicago is flat, gridded and easy to navigate.
When to go
Chicago has extreme seasons. Summers are hot and humid, winters are severely cold with lake-effect wind, and the shoulder months are excellent.
The city coming back outdoors, at 12–24°C, with the lakefront reopening and the festival season starting. May and June are ideal; April can still be raw.
Hot and humid at 26–32°C, with the beaches open, free festivals almost every weekend and the lakefront at its liveliest. Also the busiest and most expensive period.
Arguably the best window: clear, 12–24°C, with the humidity gone and the crowds thinning. October brings colour to the parks and the lake is still swimmable early in the month.
Cold — often below −10°C with wind off the lake that makes it feel far worse. The compensation is that hotel rates fall by half, the museums are empty, and everything you came for is indoors.
Worth planning around: January and February if cold bothers you at all. The wind off Lake Michigan through the downtown street grid is the reason for the city's nickname, and it is not an exaggeration.
Itinerary
Architecture first, because everything afterwards makes more sense. Then one museum, one neighbourhood and the lake.
Start with the buildings, from the water and then on foot.
One great museum, then the shoreline.
Out of downtown, which is where the city actually lives.
Bikes, beaches and the last of the buildings.
Travel tips
Chicago specifics, including two things about food that locals will thank you for knowing.
FAQ
It is the single best hour and a half of sightseeing in any American city, and it should be the first thing you do. Ninety minutes on the river with a trained docent explaining the buildings on both banks gives you the city's history and geography at once. The Chicago Architecture Center's own tours have the best-trained guides; book ahead in summer.
Three to four. One for the river cruise and the Loop's architecture, one for the Art Institute and the lakefront, one for a neighbourhood such as Pilsen or Wicker Park, and optionally one for Oak Park's Frank Lloyd Wright houses or more of the lakefront. The city is compact and well connected, so days are efficient.
Deep-dish pizza is the famous answer and locals eat it rarely. The genuine Chicago dishes are the Italian beef sandwich — thin-sliced beef in gravy with hot giardiniera, ordered 'dipped' — tavern-style thin-crust pizza cut into squares, and the Chicago hot dog with its specific set of toppings and its absolute prohibition on ketchup.
May to June and September to October. Summer is hot, humid and busy but has the beaches and constant free festivals. Winter is severe — wind off Lake Michigan regularly produces chills below −20°C — though hotel rates halve and the museums empty. Autumn is the pick: clear, mild and much quieter than summer.
The areas visitors use — the Loop, River North, the Gold Coast, Lincoln Park, Wicker Park, Pilsen and the lakefront — are safe with normal city precautions. Chicago's violent crime statistics are heavily concentrated in specific South and West Side neighbourhoods that visitors have no particular reason to be in, and the citywide figure gives a misleading picture of the tourist experience.
No. The L train covers the city with eight lines, two of which run 24 hours, and the Blue Line reaches O'Hare in 45 minutes for about $5. The Loop is walkable, the grid is logical, and the 42 km lakefront trail is best by bike. Downtown parking is expensive and unnecessary.
Live blues runs most nights across the city. Buddy Guy's Legends downtown is the best-known and reliably good. The North Side clubs are easiest to reach, while the South and West Side rooms are closer to where the music was electrified in the 1940s and 1950s. Ask locally — the smaller South Side venues are where the tradition is most alive.
Keep exploring
Places that pair well with Chicago, whether you have a few spare days or are building a longer route.
New York, United States
The densest, most walkable American city, where five distinct boroughs, a 24-hour subway and a century of immigration produce something no other city in the country resembles.
Don't miss The Metropolitan Museum — two million works across 5,000 years, and you could go every day for a month.
Explore Destination — New York CityLouisiana, United States
A city that was French, then Spanish, then French again before it was American, and which turned that inheritance into a food and music culture found nowhere else on the continent.
Don't miss Live brass and jazz on Frenchmen Street, seven nights a week, with no cover charge in half the rooms.
Explore Destination — New OrleansDistrict of Columbia, United States
A planned capital of low neoclassical buildings and wide avenues, holding the largest museum complex in the world and charging nothing to enter almost any of it.
Don't miss The National Air and Space Museum and the National Museum of African American History and Culture — free, and among the best of their kind anywhere.
Explore Destination — Washington, D.C.Lombardy, Italy
The city most Italian itineraries skip, holding one of Europe's great cathedrals, a Leonardo fresco you must book months ahead, and a design culture that shapes how the world looks.
Don't miss The roof of the Duomo, among 135 marble spires, with the Alps on the horizon on a clear day.
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