United States · Illinois
Chicago
The birthplace of the skyscraper, with a public lakefront, a serious eating city and the blues, all at a fraction of the coastal cities' swagger.
Chicago is the American city that invented the skyscraper and then spent a century arguing with itself about how to build the next one, which is why walking its downtown feels like reading a textbook at full scale. It sits on an inland sea, and the shoreline was kept public rather than sold off, so a continuous ribbon of beaches, parks and pathway runs the length of the city. Beyond the towers it is a city of neighbourhoods built by successive waves of migration, each with its own kitchens, churches and bar strips, and it carries the music those migrations produced.
Suggested stay
3–5 days
Language
English
Currency
USD
Timezone
UTC-5
Why you'll love Chicago
Architecture the city that invented the tall building and never stopped experimenting, best read from the river cutting through the middle of it
The lakefront an inland sea with a shoreline kept public, giving the city beaches, parks and a path that runs its whole length
Eating a working city's food, from immigrant neighbourhood kitchens to a restaurant scene that punches well above its billing
Music and stage where electrified blues and modern improv comedy were both born, and both still play nightly in small rooms
Best time to visit
Apr, Jul, Sep-Oct
16-29° days
41.876° N, 87.624° W
UTC-5 · America/Chicago
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Weather & when to go to Chicago
Month by month: typical highs and lows, rainfall and rain days.
✓ Best Apr, Jul, Sep-Oct
Cards tinted by calculated verdict · big number = typical daily high, small = low · hover for conditions
When to avoid Chicago
December to February. Wind coming off the lake across a flat city turns already-cold air punishing, the shoreline ices over and the short grey days push everything indoors. It is survivable, and the museums, theatres and bars are built for exactly that, but nothing about it is comfortable.
Top things to do in Chicago
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Millennium Park and Cloud Gate - the Bean, the Gehry bandshell and the video fountain
culture arts 👍 PopularAnish Kapoor's polished steel Cloud Gate warps the skyline and everyone standing under it, which is why it is the photograph everyone leaves with. The same park holds Frank Gehry's ribboned Pritzker Pavilion for free summer concerts, the Crown Fountain's giant video faces that spit water at children, and the quieter Lurie Garden behind them.
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Art Institute of Chicago - American Gothic, Nighthawks and the Impressionists
culture arts 👍 PopularThe bronze lions out front guard one of the great encyclopaedic collections: Grant Wood's American Gothic, Hopper's Nighthawks, Seurat's pointillist Sunday on La Grande Jatte and a room of Monet haystacks. The Modern Wing has its own bridge straight across to Millennium Park.
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Chicago Architecture Center river cruise - the skyline explained from the water
culture arts scenic ⭐ Highly recommendedA docent-led boat down all three branches of the Chicago River, with the buildings named and argued over as they pass overhead. It is the single best way to understand why this city looks the way it does, and the bridges opening above you are worth the ticket on their own.
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Willis Tower Skydeck - the glass ledges on the 103rd floor
scenic 👍 PopularGlass boxes cantilevered off the side of what was the world's tallest building for a quarter of a century, so you stand on nothing with the street a long way beneath your shoes. The rival view from 360 Chicago in the old Hancock tower is arguably better, because it looks back at this skyline instead of standing in it.
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Chicago Riverwalk - the promenade under the bridges
scenicA continuous walkway along the south bank of the main branch, running from the lake back into the Loop past bars, kayak docks and the historic bridgehouses. It turned a working waterway into the city's best evening stroll, and the architecture stacks up above you the whole way.
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Chicago Cultural Center - the world's largest Tiffany dome
culture arts history ⭐ Highly recommendedThe former public library is free to walk into, and Preston Bradley Hall upstairs sits under a stained-glass dome of roughly thirty thousand pieces of Tiffany glass. Locals call the building the city's front room; there are usually exhibitions and lunchtime concerts on, and almost nobody queues.
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Museum Campus - the Field Museum, Shedd Aquarium and Adler Planetarium
culture arts nature wildlifeThree institutions on one lakefront headland: Sue, the most complete Tyrannosaurus rex ever found, at the Field; beluga whales and a Pacific reef at the Shedd; and the Adler out on its point, which happens to give the best straight-on view of the skyline in the city.
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Deep-dish, tavern-style and the Italian beef - eating the city's inventions
foodDeep-dish is the famous one, a buttery pan pie with the sauce on top, though what Chicagoans actually eat most is tavern-style thin crust cut into squares. Round it out with an Italian beef dipped in its own gravy and served with hot giardiniera, and a Chicago dog dragged through the garden with no ketchup anywhere near it.
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Lakefront Trail and the city beaches - North Avenue, Oak Street and Montrose
nature wildlife scenicClose to thirty kilometres of path along the shore, shared by runners, cyclists and anyone drifting between the beaches. North Avenue Beach has the boat-shaped beach house and the volleyball nets, Oak Street sits right under the towers, and Montrose out north has the harbour and a bird sanctuary on the point.
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Chicago blues and jazz - Buddy Guy's Legends, Kingston Mines and the Green Mill
nightlife musicElectric blues was built here by musicians who came north in the Great Migration, and the clubs still run late seven nights a week. Buddy Guy's Legends in the South Loop is the institution, Kingston Mines on Halsted runs two stages until dawn, and the Green Mill up in Uptown is a Prohibition-era jazz room with its original fittings intact.
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Wrigley Field - ivy walls and the hand-turned scoreboard
culture artsThe second-oldest ballpark in the major leagues, opened in 1914, with ivy growing on the outfield brick and a scoreboard still changed by hand. The baseball season runs spring to autumn and the neighbourhood around it turns into an all-day party on game days; tours run when the team is away.
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Museum of Science and Industry - a captured U-boat and a coal mine indoors
culture arts historyHoused in the only major building left from the 1893 world's fair, out in Hyde Park. Inside sits a captured German submarine hauled up from the Atlantic, a working replica coal mine you descend into, a streamlined 1930s train and a giant walk-through model heart.
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Wicker Park, Logan Square and Pilsen - the neighbourhood city
food off beaten pathThe Blue Line out west reaches the strips where Chicagoans actually spend their evenings: vintage shops and bars around the Milwaukee Avenue crossroads in Wicker Park, boulevards and beer halls in Logan Square, and Pilsen's Mexican bakeries, taquerias and mural-covered walls along 18th Street.
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The Second City - the improv stage that stocked American comedy
culture arts nightlife musicThe Old Town theatre where improvisational comedy was formalised, and where a startling share of the last sixty years of American television comedy learned the craft. Shows run most nights, and the free improv set after the mainstage revue is a Chicago tradition.
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Navy Pier - the Centennial Wheel over the lake
scenicA former shipping and naval training pier now given over to a Ferris wheel, a stained-glass museum, a Shakespeare theatre and the boats that leave for the lake. It is unashamedly touristy, but the wheel gives you the skyline side-on and the summer fireworks over the water are genuinely good.
Best areas to stay in Chicago
$ Budget $$ Mid-range $$$ Premium
River North
Best all-round base $$Dining, galleries and hotels, walk everywhere
Explore hotels in River North →
The Loop
First-time visitors $$Skyscraper canyons, theatres, museums at the door
Explore hotels in The Loop →
Streeterville & the Gold Coast
Lakefront & shopping $$$Lakefront towers, boulevard shopping, old money
Explore hotels in Streeterville & the Gold Coast →
West Loop & Fulton Market
Food-first stays $$Converted warehouses, restaurant row, design hotels
Explore hotels in West Loop & Fulton Market →
Lincoln Park & Old Town
Leafy & family-friendly $$Leafy brownstones, free zoo, beach nearby
Explore hotels in Lincoln Park & Old Town →
Live nightly prices from Booking.com, Agoda and others, centred on Chicago
Getting to & around Chicago
Getting there
Fly into O'Hare, then the Blue Line train runs into the Loop in around three quarters of an hour, around the clock
Flight
O'Hare International Airport (ORD)
About 27 km northwest of downtown, and one of the busiest airports in the world. The Blue Line train leaves from beneath the terminals and runs into the Loop in roughly three quarters of an hour, all day and all night, which reliably beats the Kennedy Expressway; a taxi or rideshare takes about the same when traffic is clear and well over an hour in peak. Midway, the second airport and the base for much low-cost domestic flying, sits about 16 km southwest with the Orange Line running to the Loop in around half an hour.
Train
Union Station
The national long-distance rail network converges here, including the transcontinental services west and the corridor trains to Milwaukee, St Louis and Detroit; the station sits just west of the Loop across the river
Train
Millennium Station
The South Shore Line runs in from northwest Indiana and the dunes, terminating underground at the top of Grant Park
Coach
West Loop bus terminal
Long-distance and intercity coaches from across the Midwest arrive west of the Loop, within walking distance of Union Station and the Blue Line
Drive
Interstates converge from every direction: the Kennedy and Dan Ryan from the northwest and south, the Eisenhower west, the Stevenson down towards St Louis and the Skyway east into Indiana. Downtown parking is scarce and costly
Getting around
The 'L' train
Eight colour-coded lines, elevated on the ring of track that gives the Loop its name and underground beneath it; the Red and Blue lines run 24 hours
TBC
Bus
A dense grid that covers what the radial train lines miss, including the lakefront, the cross-town routes and Museum Campus
TBC
Metra
Commuter rail out to the suburbs from four downtown terminals, useful for Oak Park, the North Shore and the summer concerts at Ravinia
TBC
Walking
The centre is flat and gridded with the lake as a permanent compass, and the Riverwalk and lakefront path link most of what you came for
Free
Divvy bike share
Docks all over the city and the Lakefront Trail to ride them on, which is the fastest way to cover the shoreline in good weather
TBC
Water taxi
Seasonal river service linking Union Station, the Loop, River North and Chinatown; a commute that doubles as a sightseeing trip
TBC
Taxi & rideshare
Plentiful downtown, though the train usually wins during rush hour or after a game lets out
TBC
Day trips from Chicago
Oak Park
Half dayFrank Lloyd Wright suburb
Frank Lloyd Wright lived and worked here for twenty years, and left the densest concentration of his Prairie School houses anywhere. His Home and Studio runs tours, Unity Temple down the road is World Heritage listed, and Hemingway was born a few streets away.
Getting there
train | car
About half an hour on the Green Line, or a short drive west
Indiana Dunes National Park
Full dayDunes & lake beaches
Sand mountains, oak savanna and bog wedged between steel mills on the Indiana shore, with long swimming beaches and a climb up Mount Baldy. On a clear day the Chicago skyline floats on the horizon across the water.
Getting there
train | car
About 1 hr on the South Shore Line train from Millennium Station, or a similar drive around the bottom of the lake
Milwaukee
Full dayBrewing city & lakefront art
Calatrava's winged art museum opens and closes its brise soleil over the lake each day, the Historic Third Ward is full of warehouses turned into bars and a market hall, and the brewing and motorcycle museums cover the rest of the city's history.
Getting there
train | car
About 1.5 hr on the Hiawatha train from Union Station, or a similar drive north
Starved Rock State Park
Full daySandstone canyons & waterfalls
Eighteen narrow canyons cut into sandstone bluffs above the river, with seasonal waterfalls that run hardest after spring melt and freeze into ice columns in deep winter. The most genuine hiking within reach of the city.
Getting there
car | tour
About 2 hr drive southwest along the Illinois River
Lake Geneva
Full dayLake resort town
The resort lake where Chicago's industrial families built their summer estates after the Great Fire. A public shore path walks right past their lawns, and the mail boat still delivers post to the piers with a jumper leaping ashore at each one.
Getting there
car
About 1.5 hr drive north into Wisconsin
Galena
1-2 daysGilded-age river town
A lead-mining boom town frozen in the 1850s, its main street of brick storefronts running below hills that the last glaciers never flattened. Ulysses S. Grant's house is preserved here, and the Mississippi bluffs are half an hour further on.
Getting there
car
About 3 hr drive northwest
A little history of Chicago
The site was a portage: a low, marshy strip where the Chicago River nearly meets the waters that drain to the Mississippi, long used and long known by the Potawatomi and the other peoples of the Council of Three Fires. Jean Baptiste Point du Sable, a trader of Haitian descent, built the first permanent non-Indigenous settlement there in the 1780s. Once the canal and then the railroads made that portage permanent, everything the American interior grew, mined or slaughtered passed through Chicago, and the city built the grain elevators, stockyards and commodity exchanges to handle it.
The Great Fire of 1871 burned the centre out and, brutally, cleared the ground for the rebuilding that produced steel-framed towers and the first real school of American architecture. The World's Columbian Exposition of 1893 announced the result to the world. From 1916 the Great Migration brought hundreds of thousands of Black Americans north to the South and West Sides, transforming the city's politics and giving it gospel, electrified blues and a share of modern jazz. The twentieth century added engineering nerve on the same scale: the river reversed, the lakefront held in public hands, and the first controlled nuclear chain reaction achieved under a university sports stand.
Jean Baptiste Point du Sable establishes a trading post at the mouth of the Chicago River
Chicago is incorporated as a city, with a few thousand residents
The Illinois and Michigan Canal opens and the first railroad arrives, linking the Great Lakes to the Mississippi basin
The Great Chicago Fire destroys the centre of the city over two days
The Home Insurance Building rises on a metal frame, generally credited as the first skyscraper
The World's Columbian Exposition draws millions to the White City in Jackson Park
Engineers reverse the flow of the Chicago River, sending the city's sewage away from its drinking water
The Great Migration begins bringing Black Americans north in huge numbers, remaking the South Side and seeding Chicago blues
The first self-sustaining nuclear chain reaction is achieved beneath the stands at the University of Chicago
Millennium Park opens over former rail yards at the top of Grant Park
Know before you go
Payment
Cards everywhere
English
Everywhere
Wifi
Reliable
Power
Type A / B
120 V, 60 Hz
Dialing
+1
The months our climate read flags to avoid: the wettest, lowest-rated weather of the year.
Mobile network & SIM card
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FAQs about Chicago
▸ When is the best time to visit Chicago?
Roughly April to October. April is when the city comes back outdoors and the lakefront reopens, midsummer runs hot and busy with the festivals and beaches at full tilt, and September into October is the local favourite: warm days, cool nights and the shoreline without the crowds. December to February is the stretch to avoid unless you are specifically coming for the indoor city.
▸ Is Chicago really that cold in winter?
Yes. The city is flat and open to a very large body of water, so wind arrives with nothing to slow it and cold snaps can be genuinely severe for days at a stretch. The nickname is more likely a jab at nineteenth-century politicians than a weather report, but the wind off the lake is real enough. Chicagoans handle it by living indoors and dressing properly, and visitors can do the same.
▸ How many days do you need in Chicago?
Three full days covers the architecture, one or two of the big museums, the lakefront and a couple of neighbourhoods. Five lets you add a ball game or a blues club, get out to Hyde Park or Oak Park, and eat your way properly through the West Loop and Pilsen.
▸ Do I need a car in Chicago?
No, and it is more hindrance than help. The trains, buses and your own feet cover the centre and the inner neighbourhoods comfortably, and downtown parking is both scarce and expensive. Hire a car only for the day trips that trains do not reach, like Starved Rock, Lake Geneva or Galena.
▸ Deep-dish or thin crust?
Try deep-dish once, because it is a genuine local invention and worth understanding, but know that most Chicagoans eat tavern-style thin crust cut into squares far more often. The deep-dish places downtown are aimed squarely at visitors; the thin-crust ones in the neighbourhoods are not.
▸ Is Chicago safe for visitors?
The city's reputation is driven by violence that is heavily concentrated in particular South and West Side neighbourhoods, well away from where visitors spend their time. The Loop, River North, Streeterville, Lincoln Park, the West Loop and the lakefront feel like any other major American downtown, and normal city sense is enough: mind your phone on crowded train platforms and stay alert around the busy shopping strip late at night.
▸ Is Chicago expensive?
Less than New York or San Francisco, more than most of the Midwest. Hotels are the volatile part and swing hard with the season and the convention calendar, so a summer weekend costs far more than the same room in February. The lakefront, the beaches, the zoo, the Cultural Center and a good deal of the neighbourhood eating cost little or nothing.
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