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Chicago, United States, top 10 things to do (Wimup travel guide)
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Top 10 Things To Do in Chicago

Country
United States
Best months
May · Jun · Sep · Oct
Population
2.75
Language
English
Budget / day
$190–340
Quick answer

Give the first day to the Loop and the lakefront: the Art Institute, Millennium Park and an architecture cruise on the river, in that order, because the boat explains everything you walked past. Day two goes south to the Museum Campus and Hyde Park, or north to Lincoln Park and Wrigley Field. Keep the third for the neighborhoods, which is where Chicago is itself: Pilsen, Logan Square, Bronzeville.

Chicago Travel Guide

▶ Video guideOpen the film page (28:07) →

Chicago is the American city that takes its buildings seriously. The skyscraper was worked out here after the fire of 1871, and the result is a downtown you read like a timeline. The lake does the rest: the public shoreline is a beach and an 18.5-mile path rather than a wall of private frontage.

The 10 best things to do in Chicago

The Art Institute of Chicago, Chicago, United States
1

The Art Institute of Chicago

Museum· 111 S Michigan Ave, The Loop

The second-largest art museum in the United States, and the one American collection that can hang Impressionism, the Chicago School and contemporary work in a single afternoon. Seurat's La Grande Jatte, Hopper's Nighthawks and Wood's American Gothic are all here, in rooms quieter than their fame suggests.

Time2 to 4 hours
CostTicketed
Best atWeekday mornings
TipUse the Modern Wing entrance on Monroe Street when the Michigan Avenue lions have a queue under them.
Map↗ Website
Take the architecture cruise on the river, Chicago, United States
2

Take the architecture cruise on the river

Tour· 112 E Wacker Dr, The Loop

Ninety minutes on the Chicago River with a Chicago Architecture Center docent, and the best hour of orientation the city sells. You pass the Wrigley Building, Marina City, the Merchandise Mart and Studio Gang's rippling towers from water level, which is the angle they were drawn to be seen from. The dock is at the Michigan Avenue Bridge.

Time90 minutes
CostTicketed
Best atLate afternoon
TipTake the open upper deck and bring a layer. The river runs colder than the street.
Map↗ Website
Millennium Park and Cloud Gate, Chicago, United States
3

Millennium Park and Cloud Gate

Park· 201 E Randolph St, The Loop

Built over a rail yard and opened in 2004, this is the civic engineering that changed how Chicago treats its front yard. Kapoor's Cloud Gate throws the skyline back at itself, Plensa's Crown Fountain spits water at children all summer, and Gehry's Pritzker Pavilion carries the free concerts.

Time1 hour
CostFree
Best atEarly morning or after dark
TipCloud Gate is empty at seven in the morning and surrounded by ten. Photograph it early.
Map↗ Website
Skydeck Chicago at Willis Tower, Chicago, United States
4

Skydeck Chicago at Willis Tower

Viewpoint· 233 S Wacker Dr, The Loop

The 103rd floor of the tower the city still calls Sears, and the highest observation deck in the country. The Ledge is a set of glass boxes cantilevered off the side at 1,353 feet, and standing in one is a physical experience rather than a photo opportunity. 360 Chicago looks back at this skyline instead of down on it.

Time1 to 2 hours
CostTicketed, timed entry
Best atThe hour before sunset
TipBook a timed slot. The queue in the lobby is where the time goes.
Map↗ Website
The Field Museum, Chicago, United States
5

The Field Museum

Museum· 1400 S DuSable Lake Shore Dr, Museum Campus

Natural history on the scale of a city that built itself around a world's fair. Sue, the most complete Tyrannosaurus rex ever found, has a hall upstairs; the titanosaur Máximo fills the ground floor. The Ancient Egypt rooms are built around a mastaba you walk into. One of three buildings on the Museum Campus.

Time3 hours
CostTicketed
Best atWeekday mornings
TipIllinois residents get free days through the year
Map↗ Website
A game at Wrigley Field, Chicago, United States
6

A game at Wrigley Field

Sport· 1060 W Addison St, Lakeview

Opened in 1914 and home to the Cubs since 1916, which makes it the second-oldest ballpark in Major League Baseball. The ivy on the outfield wall, the hand-turned scoreboard and the rooftop bleachers across Sheffield are reasons to go even if the sport means nothing to you. The neighborhood is half the event.

Time3 to 4 hours
CostTicketed
Best atA weekday afternoon game
TipBallpark tours run on selected non-game days and get you onto the warning track and into the dugout.
Map↗ Website
Griffin Museum of Science and Industry, Chicago, United States (Wimup)
7

Griffin Museum of Science and Industry

Museum· 5700 S DuSable Lake Shore Dr, Hyde Park

The largest science museum in the Western Hemisphere, in the one building left standing from the 1893 World's Columbian Exposition. A German U-boat captured in 1944 sits in a purpose-built hall below ground, a full-size coal mine runs under the floor, and a model railway covers Chicago to Seattle.

Time3 to 4 hours
CostTicketed
Best atWeekday mornings
TipGoing aboard the U-505 is a separate ticket from museum entry, and it is the one to add.
Map↗ Website
Frederick C. Robie House, Chicago, United States (Wimup)
8

Frederick C. Robie House

Architecture· 5757 S Woodlawn Ave, Hyde Park

Frank Lloyd Wright finished this house in 1910 and it remains the clearest statement of the Prairie style anywhere: horizontal to the point of provocation, with a roof that reaches far past the walls and art glass that pulls the outside in. In 2019 it became one of eight Wright buildings on the UNESCO World Heritage List.

Time1 hour
CostTicketed, guided tours
Best atMorning
TipIt is a fifteen-minute walk from the Griffin museum
Map↗ Website
Buddy Guy's Legends, Chicago, United States (Wimup)
9

A blues night at Buddy Guy’s Legends

Music· 700 S Wabash Ave, South Loop

Chicago electrified the blues, and this is the room that keeps the fact current rather than commemorated. Buddy Guy owns it, the bookings run seven nights a week, and the lunchtime acoustic sets happen without the crowd the evening brings. The club moved to this South Loop address in 2010, and Guy has played a January residency here for years.

TimeAn evening
CostTicketed for evening sets
Best atLate evening
TipKingston Mines up in Lincoln Park runs two stages and later hours if the night is not finished.
Map↗ Website
Lincoln Park Zoo, Chicago, United States (Wimup)
10

Lincoln Park Zoo

Free· 2001 N Clark St, Lincoln Park

Opened in 1868 and still free to walk into, which is rare enough in the United States to be the headline. It sits inside Lincoln Park, so a visit folds into a lakefront afternoon: the conservatory next door, the Alfred Caldwell Lily Pool behind it, the Chicago History Museum at the south end. Small enough to do properly in two hours rather than endure for four.

Time2 hours
CostFree
Best atMorning
TipThe Lily Pool is a Caldwell prairie-style landscape hidden behind a fence
Map↗ Website

All 10, mapped

Chicago · 10 spots

Chicago travel FAQ

How many days do you need in Chicago?+
Three. One for the Loop, the Art Institute and an architecture cruise, one for the Museum Campus or Hyde Park, and one for the neighborhoods and a long dinner. A fourth day buys you Oak Park or the Indiana Dunes without rushing either.
What is the best time of year to visit Chicago?+
May to October. June and September are the sweet spot: warm, long evenings, and the festival calendar running without August’s humidity. Winter is genuinely cold off the lake, and while the museums and the music do not care, walking between them becomes work.
Is Chicago walkable?+
The Loop, the lakefront and any single neighborhood are walkable. The distances between neighborhoods are not, because the city is flat and enormous. Walk within an area and take the L or a bus between them; the Red and Blue Lines run 24 hours.
Where should you stay in Chicago?+
The Loop and River North put you inside walking distance of the museums, the river and the theatre district, which suits a first visit. The West Loop trades that for the best eating in the city. Wicker Park and Logan Square are cheaper, livelier at night and about 20 minutes from downtown on the Blue Line.
Do people in Chicago actually eat deep-dish pizza?+
Not often. Deep-dish is worth doing once and it is genuinely good, but the everyday Chicago pizza is tavern-style: thin, crisp, cut into squares and ordered from the bar down the street. Have both and decide.
Where Chicago eats out

Best restaurants in Chicago

Ten kitchens worth planning a night around, from the only three-star tasting menu in the city to a Filipino counter in Ukrainian Village.
Three stars
West Loop

Smyth

Restaurant · 177 N Ada St

John Shields and Karen Urie-Shields cook a tasting menu around produce from one Kentucky farm. The only three-star restaurant in the 2026 Chicago Michelin guide.

Map↗ Website
Two stars
Lincoln Park

Alinea

Restaurant · 1723 N Halsted St

Grant Achatz has been rewriting what a tasting menu can be here since 2005. Seats are bought in advance like concert tickets.

Map↗ Website
Oriole
Two stars
Fulton River District

Oriole

Restaurant · 661 W Walnut St

Noah Sandoval cooks a New American tasting menu at the end of a freight corridor off Walnut Street. Two Michelin stars, and a James Beard award in 2025.

Map↗ Website
Two stars
West Loop

Ever

Restaurant · 1340 W Fulton St

Curtis Duffy's room after Grace, holding two stars in every guide since 2021. Deliberately calm, and a fixed run of precise small courses.

Map↗ Website
Two stars
Ukrainian Village

Kasama

Restaurant · 1001 N Winchester Ave

Tim Flores and Genie Kwon run a Filipino bakery by day and a tasting menu by night from one storefront.

Map↗ Website
One star
River North

Topolobampo

Restaurant · 445 N Clark St

Rick Bayless opened this beside Frontera Grill in 1989 and it has held a Michelin star for years. Regional Mexican researched properly, with a seasonal mole list.

Map↗ Website
Southern
Hyde Park

Virtue

Restaurant · 1462 E 53rd St

Erick Williams cooks modern Southern food in Hyde Park, and this is the restaurant that made the South Side a dinner destination for the whole city.

Map↗ Website
Girl & the Goat
Sharing plates
West Loop

Girl & the Goat

Restaurant · 809 W Randolph St

Stephanie Izard’s West Loop room, open since 2010 and still the hardest ordinary reservation in Chicago. Wood fire, sharing plates, and goat on the menu in several forms.

Map↗ Website
Pasta
West Loop

Monteverde

Restaurant · 1020 W Madison St

Sarah Grueneberg makes the pasta in a glass-walled pastificio at the front of the dining room. Open since 2015 and the reason Madison Street has a queue on a Tuesday.

Map↗ Website
Neighborhood
Logan Square

Lula Cafe

Restaurant · 2537 N Kedzie Blvd

The restaurant that started Logan Square’s run, cooking seasonal, mostly organic food since 1999. Brunch is the meal people plan their weekend around.

Map↗ Website
After dark

Best bars in Chicago

Ten rooms for a drink: a cocktail laboratory in Fulton Market, a whiskey bar with a film night, and taverns that have not changed since the 1950s.
The Aviary
Cocktails
Fulton Market

The Aviary

Bar · 955 W Fulton Market

Grant Achatz's cocktail laboratory in Fulton Market, where drinks arrive in purpose-made glassware and the ice is engineered rather than scooped.

Map↗ Website
Japanese
West Loop

Kumiko

Bar · 630 W Lake St

Julia Momose's Japanese-influenced bar on Lake Street, precise about ingredients and about pacing. The non-alcoholic list is built with the same seriousness.

Map
Tiki
River North

Three Dots and a Dash

Bar · 435 N Clark St

A tiki basement down an alley off Hubbard Street, pouring rum drinks in ceramic mugs since 2013. A party rather than a quiet room.

Map
Amaro
Logan Square

Billy Sunday

Bar · 3143 W Logan Blvd

An amaro-led bar on Logan Boulevard with a back bar of bottles most places do not stock, named after the evangelist who campaigned for Prohibition.

Map
Tavern
Logan Square

Longman & Eagle

Bar · 2657 N Kedzie Ave

A Logan Square tavern with a whiskey list, a kitchen that has held a Bib Gourmand, and six rooms upstairs if the evening goes long.

Map
Dive
Old Town

Old Town Ale House

Bar · 219 W North Ave

Open since 1958 across the street from Second City, papered with the owner’s own paintings of politicians and regulars. It opens early and closes very late.

Map
Whiskey
Lincoln Park

Delilah’s

Bar · 2771 N Lincoln Ave

A Lincoln Park punk bar with one of the deepest whiskey lists in the city, a serious beer selection and a film night upstairs. Loud, dark and unbothered.

Map
Beer
Bucktown

Map Room

Bar · 1949 N Hoyne Ave

A Bucktown beer bar with a wall of atlases, a very long tap and bottle list and coffee in the morning. It calls itself a travellers’ tavern and behaves like one.

Map
Brewery
North Center

Half Acre Beer Company

Bar · 4257 N Lincoln Ave

A Chicago brewery with a taproom on Lincoln Avenue in North Center, pouring its own beer next to a kitchen. The tap list moves faster than the cans reach shops.

Map
Rooftop
The Loop

Cindy’s

Bar · 12 S Michigan Ave

The rooftop of the Chicago Athletic Association hotel, under a glass gable looking straight across Michigan Avenue at Millennium Park. Arrive before sunset.

Map
Beyond the big three

Best museums and galleries in Chicago

The collections past the Art Institute, the Field and the Griffin, several of which cost nothing to walk into.
Museum of Contemporary Art Chicago
Contemporary
Streeterville

Museum of Contemporary Art Chicago

Museum · 220 E Chicago Ave

A block off Michigan Avenue, with a collection that runs from Warhol and Sherman to work made this year, and a theatre and a terrace behind it.

Map↗ Website
Shedd Aquarium
Family
Museum Campus

Shedd Aquarium

Museum · 1200 S DuSable Lake Shore Dr

The middle building of the Museum Campus, holding an oceanarium that looks out at Lake Michigan through a glass wall. Illinois residents get free days through the year.

Map↗ Website
Adler Planetarium
Science
Museum Campus

Adler Planetarium

Museum · 1300 S DuSable Lake Shore Dr

The first planetarium in the Western Hemisphere, on a spit of land with the best free skyline view in Chicago behind it. Illinois residents get free days here too.

Map↗ Website
National Museum of Mexican Art
Free
Pilsen

National Museum of Mexican Art

Museum · 1852 W 19th St

The largest Mexican art collection of its kind in the United States, in the middle of Pilsen, and free every day of the year.

Map↗ Website
Chicago History Museum
History
Lincoln Park

Chicago History Museum

Museum · 1601 N Clark St

The city explained in one building at the south end of Lincoln Park, from the fire and the stockyards to the 1968 convention and house music.

Map↗ Website
DuSable Black History Museum and Education Center
History
Washington Park

DuSable Black History Museum and Education Center

Museum · 740 E 56th Pl

The oldest independent African American museum in the country, founded in 1961 and named for the Haitian trader who settled the mouth of the river. Free on Wednesdays.

Map↗ Website
Driehaus Museum
House museum
River North

Driehaus Museum

Museum · 40 E Erie St

A restored Gilded Age mansion off Michigan Avenue, kept as an interior rather than a gallery, with Tiffany glass and the decorative arts of the 1880s in place.

Map↗ Website
Free
Hyde Park

Smart Museum of Art

Museum · 5550 S Greenwood Ave

The University of Chicago’s art museum in Hyde Park, small, sharply curated and free, and a ten-minute walk from Robie House.

Map↗ Website
Free
South Loop

Museum of Contemporary Photography

Museum · 600 S Michigan Ave

Columbia College’s photography museum on South Michigan Avenue, free, and the most consistently interesting small gallery in the Loop.

Map↗ Website
Free
South Shore

Stony Island Arts Bank

Museum · 6760 S Stony Island Ave

Theaster Gates turned a derelict 1923 savings bank into an archive and gallery for the South Side, holding record collections and a library. Free.

Map↗ Website
Read the skyline

The buildings worth a detour in Chicago

Eight buildings that carry the argument, from an 1891 load-bearing brick tower to a balcony line that behaves like water.
1888
The Loop

The Rookery

Building · 209 S LaSalle St

Burnham and Root finished it in 1888 and Frank Lloyd Wright remodelled the light court in 1905, so one building carries two eras at once. The lobby is open.

Map↗ Website
Chicago Cultural Center
Free
The Loop

Chicago Cultural Center

Building · 78 E Washington St

The old public library, free to walk into, holding the largest stained-glass Tiffany dome in the world under a staircase of Carrara marble.

Map↗ Website
Auditorium Theatre
1889
The Loop

Auditorium Theatre

Building · 50 E Ida B. Wells Dr

Adler and Sullivan’s 1889 hall, with Sullivan’s gold ornament and Adler’s acoustics, built inside a block that also held a hotel and offices. Still a working theatre.

Map↗ Website
1891
The Loop

Monadnock Building

Building · 53 W Jackson Blvd

Two halves of an argument in one block: the north half of 1891 is load-bearing brick six feet thick at the base, the south half of 1893 is steel frame.

Map
Marina City
1964
River North

Marina City

Building · 300 N State St

Bertrand Goldberg’s corn cobs of 1964, two concrete towers with petal balconies and a marina underneath, designed to bring people back downtown when nobody lived there.

Map
Aqua Tower
2009
Lakeshore East

Aqua Tower

Building · 225 N Columbus Dr

Jeanne Gang’s 2009 tower, where each floor slab steps out by a different amount to create a rippling surface that behaves like water and also shades the glass.

Map
1899
The Loop

The Sullivan Center

Building · 1 S State St

Louis Sullivan's 1899 department store, with cast-iron ornament wrapped around the corner at State and Madison. Look at two floors, then look up.

Map
Tribune Tower
1925
Streeterville

Tribune Tower

Building · 435 N Michigan Ave

The neo-Gothic winner of a 1922 competition, with fragments of the Parthenon, the Great Wall and dozens of other sites set into its base at street level.

Map
What the city sounds like

Best live music and comedy in Chicago

Eight rooms covering the blues, jazz, indie rock, the orchestra and the theatre that invented modern improv.
Green Mill Cocktail Lounge
Jazz
Uptown

Green Mill Cocktail Lounge

Venue · 4802 N Broadway

An Uptown jazz room open since 1907, with its booths, its ceiling and its rules: quiet during the sets. The Sunday poetry slam started here in 1986.

Map↗ Website
Blues
Lincoln Park

Kingston Mines

Venue · 2548 N Halsted St

Two stages running alternating sets so the blues never stops, in Lincoln Park since 1968. It closes later than almost anything else in the city.

Map↗ Website
Comedy
Old Town

The Second City

Venue · 1616 N Wells St

The improv theatre that produced most of the cast lists of American comedy since 1959, still running multiple stages a night on Wells Street.

Map↗ Website
Comedy
Near North Side

iO Theater

Venue · 1501 N Kingsbury St

The home of long-form improv, where the Harold was worked out, with four stages and a training centre on Kingsbury Street.

Map↗ Website
Metro
Rock
Wrigleyville

Metro

Venue · 3730 N Clark St

A 1,100-capacity rock club by Wrigley Field, open since 1982, where Chicago bands play the room they grew up wanting to play. Smart Bar is in the basement.

Map↗ Website
Live music
Pilsen

Thalia Hall

Venue · 1807 S Allport St

An 1892 hall in Pilsen modelled on the Prague opera house, restored into one of the best-sounding mid-size venues in the country, with a bar and a restaurant attached.

Map↗ Website
Indie
Ukrainian Village

Empty Bottle

Venue · 1035 N Western Ave

A storefront on Western Avenue that has booked touring and local indie acts since 1992, cheap and unpolished on purpose.

Map↗ Website
Symphony Center
Classical
The Loop

Symphony Center

Venue · 220 S Michigan Ave

Home of the Chicago Symphony Orchestra since 1904, in a Daniel Burnham hall on Michigan Avenue across from the Art Institute.

Map↗ Website
Where the city lives

Chicago neighborhoods worth your time

Ten of the 77 community areas, each with a reason to spend an afternoon and a train that gets you there.
Pink Line
Lower West Side

Pilsen

18th St & Ashland Ave

Mexican Chicago on the Lower West Side, with murals along 16th Street, the National Museum of Mexican Art and taquerias on 18th. Pink Line to 18th.

Map
Logan Square
Blue Line
Logan Square

Logan Square

Logan Blvd & Kedzie Ave

A boulevard neighborhood that turned into the city's restaurant belt without losing its Sunday farmers market. Lula Cafe and Longman & Eagle are here.

Map
Blue Line
West Town

Wicker Park and Bucktown

Milwaukee Ave & Damen Ave

The 1990s music scene grew here and the shopping stayed. The six-corner junction at Milwaukee, North and Damen is the centre of it. Blue Line to Damen.

Map
Green Line
Near West Side

West Loop and Fulton Market

Randolph St & Halsted St

Meatpacking warehouses turned into the densest restaurant strip in Chicago, with Randolph Street as the spine. Green or Pink Line to Morgan.

Map
Metra
Hyde Park

Hyde Park

53rd St & Lake Park Ave

The University of Chicago, Robie House, the Griffin museum and Promontory Point, all within a mile of each other on the lake. Metra Electric beats the bus.

Map
Red Line
Edgewater

Andersonville

Clark St & Foster Ave

A Swedish neighborhood on Clark Street that became one of the city's main LGBTQ+ districts, with independent bookshops and no chains to speak of.

Map
Chinatown
Red Line
Armour Square

Chinatown

Wentworth Ave & Cermak Rd

One of the few American Chinatowns still growing, with a riverside park, dim sum on Wentworth and a library architects come to look at.

Map
Green Line
Douglas

Bronzeville

35th St & King Dr

The centre of Black Chicago during the Great Migration, where Louis Armstrong, Gwendolyn Brooks and Ida B. Wells lived and worked. Greystones and jazz history.

Map
Brown Line
Lincoln Square

Lincoln Square

Lincoln Ave & Lawrence Ave

The old German quarter around Lincoln Avenue, with a pedestrian block, the Old Town School of Folk Music and a beer garden. Brown Line to Western.

Map
Blue Line
West Town

Ukrainian Village

Chicago Ave & Damen Ave

Golden-domed churches, low two-flats and a quiet grid that holds Kasama and the Empty Bottle within a few blocks of each other. Blue Line to Division, then walk west.

Map
Out of town

Best day trips from Chicago

Six trips within reach, four of them by train, including a national park on the lake and Frank Lloyd Wright’s own front door.
By train
West suburbs

Oak Park

About 25 minutes by train

Frank Lloyd Wright lived and worked here for twenty years, and the suburb holds his Home and Studio, Unity Temple and two dozen other Wright buildings within a walk.

Map↗ Website
Indiana Dunes National Park
By train
Indiana lakeshore

Indiana Dunes National Park

About 90 minutes by train

Fifteen miles of dunes, beach and marsh on the far shore of Lake Michigan, with the skyline visible on a clear day. The South Shore Line runs to Dune Park.

Map↗ Website
Milwaukee
By train
Wisconsin

Milwaukee

About 90 minutes by Amtrak

North on Amtrak’s Hiawatha, for the Santiago Calatrava wing on the art museum, the Historic Third Ward and a beer culture that predates Chicago’s.

Map↗ Website
Evanston and the Bahá’í House of Worship
By train
North shore

Evanston and the Bahá’í House of Worship

About 45 minutes by L

The Purple Line ends at Linden, a short walk from the only Bahá'í temple in North America, a nine-sided dome of cast concrete lace finished in 1953.

Map↗ Website
Starved Rock State Park
By car
Illinois River valley

Starved Rock State Park

About 2 hours by car

Sandstone canyons and seasonal waterfalls above the Illinois River. There is no useful train, and it fills up on summer weekends.

Map↗ Website
By car
Northwest Illinois

Galena

About 3 hours by car

A nineteenth-century lead-mining town in the hills near the Mississippi, with a main street that was never rebuilt and Grant's house above it.

Map↗ Website
What's on

Festivals & annual events in Chicago (2026)

Time your trip around the dates the city plans its year on.
March

St. Patrick's Day and the river dyeing

The Chicago River is dyed green from a boat on the Saturday of the holiday weekend, ahead of the downtown parade.

June

Chicago Blues Festival

The largest free blues festival in the world, run by the city since 1984 and centred on Millennium Park.

July

Taste of Chicago

The city's food festival in Grant Park, restaurants and food trucks over five days with free concerts alongside.

July

Lollapalooza

Four days and eight stages across Grant Park, with the skyline behind the main stage. Book a hotel months out.

August

Chicago Air and Water Show

Military and civilian aerobatics over the lakefront, watched free from North Avenue Beach and the rooftops around it.

September

Chicago Jazz Festival

Four free days in Millennium Park over the Labor Day weekend, and one of the largest free jazz festivals anywhere.

October

Bank of America Chicago Marathon

One of the six World Marathon Majors, run through 29 neighborhoods on a flat course that produces records.

November

Christkindlmarket

A German Christmas market on Daley Plaza, open daily from 20 November to 24 December, with further markets elsewhere.

Getting around

Chicago transport & airports

How to arrive, and how to move once you have.
ORD

O'Hare International Airport (ORD)

Seventeen miles northwest of the Loop and one of the busiest airports in the world. The CTA Blue Line runs from under Terminal 2 into downtown around the clock, in about 45 minutes.

Map↗ Website
MDW

Midway International Airport (MDW)

Ten miles southwest of downtown, smaller and quicker to move through, and the base for most low-cost flying into Chicago. The Orange Line reaches the Loop in half an hour.

Map↗ Website
CTA

CTA 'L' trains and buses

Eight colour-coded rail lines built around the elevated Loop, plus buses filling the gaps. The Red and Blue Lines run 24 hours. Tap a Ventra card or a contactless bank card.

Map↗ Website
Rail

Metra and Amtrak at Union Station

Metra runs 11 commuter lines out to the suburbs, and Union Station is also Amtrak's Midwest hub. Metra Electric from Millennium Station is the quick way to Hyde Park.

Map↗ Website
Traditional food

Must-try dishes in Chicago, United States

The plates to order before you leave town.
Deep-dish pizza, Chicago (Wimup travel guide)

Deep-dish pizza

A buttery crust pressed up the side of a pan, cheese under the sauce, and a 40-minute bake. Eat it once.

Italian beef, Chicago (Wimup travel guide)

Italian beef

Thin-sliced roast beef in seasoned jus on a French roll, with sweet peppers or giardiniera. Order it dipped.

Jibarito, Chicago (Wimup travel guide)

Jibarito

A sandwich invented in Humboldt Park in the 1990s, using flattened fried plantains in place of bread.

Maxwell Street Polish, Chicago (Wimup travel guide)

Maxwell Street Polish

A grilled Polish sausage buried under fried onions and mustard, named for the market street it came from.

Tavern-style thin crust

The pizza Chicago actually eats: cracker-thin and cut into squares rather than wedges. Ask for it party cut.

Chicago-style hot dog

Mustard, onion, relish, a pickle spear, tomato, sport peppers and celery salt on a poppy seed bun.

Flaming saganaki

Kefalograviera set alight at the table in Greektown, put out with lemon and eaten with bread.

Rainbow cone

Chocolate, strawberry, Palmer House, pistachio and orange sherbet stacked in slices, sold here since 1926.

Chicago fact sheet

Chicago at a glance

The essentials worth knowing before you go.
Country
United States
Region
Illinois · Cook County
Population
2.75M in the city, 9.6M in the metropolitan area (2020 census)
Founded
Incorporated as a town in 1833 · as a city in 1837
Nickname
The Windy City · The Second City · Chi-Town
Language
English
Currency
US dollar (USD)
Time zone
UTC-6 · UTC-5 from March to November
Calling code
+1 312 · 773 · 872
Airports
ORD · MDW
Power
120V · Type A & B
Emergency
911 police, ambulance and fire
Ideal length
3 days
Getting around
'L' trains, buses & walking
Tourism board
Official site

Interesting facts

  • The fire of 1871 cleared the centre, and the rebuilding produced the 1885 Home Insurance Building, credited as the first skyscraper.
  • Chicago is divided into 77 community areas, drawn in the 1920s and still the units the city uses to publish its own data.
  • Engineers reversed the flow of the Chicago River in 1900 so the city's sewage ran towards the Mississippi rather than into Lake Michigan.
  • Robie House and Unity Temple were among eight Frank Lloyd Wright buildings inscribed on the UNESCO list in July 2019.
  • The Chicago Cultural Center holds the largest stained-glass Tiffany dome in the world, and charges nothing to walk in and stand under it.

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Photo credits (19)