Chicago is a big city that is easy to read: a lakefront of parks and beaches, a compact downtown ringed by elevated trains, and neighbourhoods strung out along the 'L'. Deep-dish pizza at Lou Malnati's is covered on the USA page; this page adds the rest of a first trip: the Art Institute and Millennium Park, the view from the Skydeck, a ride around the Loop, the lake by bike and by boat, Frank Lloyd Wright's Oak Park, and the blues, comedy and baseball that fill the evenings.
Most of it sits in three areas. The Loop has the Art Institute, Millennium Park, Willis Tower and the elevated tracks; the lakefront south of it has the Field Museum, and to the north Navy Pier and the beaches; the North Side has Second City, Kingston Mines and Wrigley Field. Oak Park is a train ride west.
See Nighthawks and La Grande Jatte at the Art Institute
Art Institute of Chicago, 111 South Michigan Avenue
3 hours to a full dayBook ahead
Stand in front of Nighthawks, American Gothic and Seurat's La Grande Jatte in a museum many visitors give a whole day.
What it is
The Art Institute, behind the two bronze lions at 111 South Michigan Avenue, holds more than 300,000 works, and its Impressionist and Post-Impressionist galleries are why many visitors give it a whole day: Monet, Cassatt, Renoir, Degas and Seurat's A Sunday on La Grande Jatte. Two American paintings everyone knows hang here too, Grant Wood's American Gothic and Edward Hopper's Nighthawks. The Modern Wing, opened in 2009, covers Picasso, Matisse, Dalí and Magritte. The main building itself went up for the 1893 World's Fair.
How to do it
Buy tickets online, where the Fast Pass skips the entrance queues. The Modern Wing has its own entrance at 159 East Monroe Street. The free daily gallery tours help if you only have a morning.
Good to know
Children 13 and under go free, and Illinois residents get free days.
Walk under Cloud Gate and picnic at a free Millennium Park concert
Millennium Park, 201 East Randolph Street
1 to 2 hoursFree
Walk under the Bean to see your reflection multiplied, then picnic on the lawn at a free summer concert.
What it is
Millennium Park, at 201 East Randolph Street, is free. Cloud Gate is Anish Kapoor's 110-ton mirror of 168 stainless steel plates that everyone calls the Bean; under its arch is the omphalos, the hollow 27 feet up that multiplies your reflection. Nearby, Jaume Plensa's Crown Fountain shows giant video faces on two glass towers, and in summer children splash in the pool between them. Frank Gehry's Jay Pritzker Pavilion hosts free concerts, among them the Grant Park Music Festival orchestra several evenings a week from June to August.
How to do it
It is open daily from 6 am to 11 pm. Start at Cloud Gate and walk under its arch. For the concerts, bring a picnic for the lawn. In winter McCormick Tribune Plaza becomes a free ice rink, with skates to rent.
Good to know
Cloud Gate reopened in June 2024 after almost a year of plaza works.
Ride along Lake Michigan with the lake on your right and the towers on your left, on a trail just for bikes.
What it is
Chicago's front yard is an 18-mile path along Lake Michigan, from Ardmore Avenue in the north to 71st Street in the south, and since 2018 it has been split into a bike trail and a separate pedestrian trail, so riding it is relaxed. The classic stretch runs north from Museum Campus past Navy Pier to North Avenue Beach, with the lake on your right and the towers on your left.
How to do it
Rent a Divvy bike in the app: in 2026 a single ride costs $1 to unlock plus 20 cents a minute on a classic bike, and a $19.90 day pass gives each classic-bike ride three free hours.
Good to know
In autumn 2026 the Park District is patching the asphalt section by section between 63rd Street and Foster Avenue, so expect short work-zone detours.
Time needed
2 to 3 hours
Best time
A dry morning; October is usually the driest month
Step into a glass box 1,353 feet above the street, with 1.5 inches of glass between your feet and the city grid.
What it is
The Skydeck, on the 103rd floor of Willis Tower, looks over the whole grid of the city, with sunrises over Lake Michigan to the east and sunsets to the west. The draw is The Ledge: glass boxes 1,353 feet up that stick out 4.3 feet from the tower, with 1.5 inches of glass between your feet and the street. On the way up you pass The Chicago Museum, on the city's rise.
How to do it
Enter on Jackson Boulevard, on the south side. In 2026 general tickets start at $32 for adults and $22 for ages 3 to 11; Expedited Entry, from $55, lets you pick a time slot and take an express line to the lift. Quincy station, on the 'L', is a block away.
Good to know
From 1 October to 28 February it opens 9 am to 8 pm, Saturdays to 9 pm, with last entry 30 minutes before closing.
Hear Chicago blues at Kingston Mines and Buddy Guy's Legends
Kingston Mines, Lincoln Park, and Buddy Guy's Legends, South Loop
An eveningNo booking needed
Two bands trading hour-long sets until 4 am at Kingston Mines, or Buddy Guy's own club in the South Loop.
What it is
Two rooms cover Chicago's electric blues. Kingston Mines, at 2548 North Halsted Street in Lincoln Park, has been a blues club since 1968: on the nights it opens, two bands trade hour-long sets on two stages until 4 am, or 5 am on Saturdays. Buddy Guy's Legends, 700 South Wabash in the South Loop, is the guitarist's own club: a free, all-ages dinner set in the early evening, then the over-21 show. For jazz, the Green Mill in Uptown has live sets every night from 8 pm.
How to do it
Kingston Mines opens Thursday to Saturday, for a $15 cover on Thursday and $20 at weekends. Legends opens Wednesday to Sunday, with the over-21 show from 9 or 9:30 pm, for $15, or $25 on Fridays and Saturdays.
Good to know
Neither takes reservations, Legends' tables fill by 7:30 pm on weeknights, and both ask for photo ID.
Wrigley Field, 1060 West Addison Street, Wrigleyville
An afternoon or eveningBook ahead
Watch the Cubs under outfield ivy planted in 1937, beside a scoreboard still turned by hand, in a ballpark opened in 1914.
What it is
Wrigley Field opened in 1914, which makes it the oldest ballpark in the National League and the second-oldest in the majors after Boston's Fenway Park. Much of what makes it famous is old too: the ivy on the outfield walls, planted in 1937, and the scoreboard, still turned by hand. The Cubs, World Series winners in 2016, play their home games here through the regular season in front of up to 41,649 fans.
How to do it
The park sits in a mainly residential neighbourhood with no parking lots, so take the Red Line to Addison, beside the ballpark. Buy tickets ahead for weekend games. Guided ballpark tours take you through the seating bowl, the bleachers and onto the field.
Meet SUE the Tyrannosaurus rex in its own suite, then walk into an Egyptian tomb and past the man-eating lions of Tsavo.
What it is
The Field Museum, on the lakefront Museum Campus, is home to SUE, the Tyrannosaurus rex skeleton unveiled in 2000 and moved in 2018 to its own suite in the Griffin Halls of Evolving Planet. Inside Ancient Egypt takes you into the mastaba tomb of Unas-Ankh, with 23 human mummies, and the Mammals of Africa hall holds the man-eating lions of Tsavo.
How to do it
It is at 1400 South DuSable Lake Shore Drive. From the Loop, take the Red, Orange or Green Line to Roosevelt and walk east to the lake. In 2026 general admission is $30, Chicago residents pay $21, and Illinois residents get in free on Wednesdays. Buy online before you go.
Good to know
It opens daily from 9 am to 5 pm, with last entry at 4 pm, and closes on Thanksgiving and Christmas Day.
Tour Frank Lloyd Wright's Home and Studio in Oak Park
Oak Park, 11 miles west of the Loop
Half a dayBook ahead
See where Frank Lloyd Wright developed the Prairie style, then walk to Unity Temple, his World Heritage public building.
What it is
Frank Lloyd Wright lived and worked in Oak Park, 11 miles west of the Loop, from 1889 to 1909, and the village holds the largest collection of his buildings. At the Home and Studio, 951 Chicago Avenue, he and his associates developed the Prairie style. Unity Temple, 875 Lake Street, built in 1905 to 1908, is Wright's only surviving public building of the Prairie period and a World Heritage Site.
How to do it
Start at the Home and Studio; entry is by guided tour only, 60 minutes for $24, daily from 10 am to 4 pm. The $38 Inside and Out ticket adds a 45-minute self-guided audio walk past the houses of the historic district, in eight languages. Then walk to Unity Temple, with 45-minute guided tours for $20, Monday to Saturday. Two CTA lines and Metra run to Oak Park.
Good to know
Book ahead; interior tours are not recommended for children under 8.
Chicago's everyday food comes from a counter: an all-beef dog that never sees ketchup, and an Italian beef dipped bread and all.
What it is
Deep dish gets the fame, but Chicago's everyday food comes from a counter. The Chicago dog is an all-beef frank on a poppy seed bun with yellow mustard, chopped white onion, sweet relish, a dill pickle spear, tomato, sport peppers and a dash of celery salt, and never ketchup. The Italian beef, which had a starring role in The Bear, is sliced beef scooped from its jus onto a roll.
How to do it
Portillo's in the Loop and South Loop is the easy start for a dog, and family-owned Dave's Red Hot, open since 1938, is one of the city's oldest stands. Order the beef sweet, with roasted peppers, or hot, with giardiniera, pickled vegetables, or both; then wet, with extra jus, or dipped, bread and all. Al's began in 1938 as a beef stand on a Little Italy corner, and Mr. Beef in River North is another classic.
The cheapest sightseeing in the city: a window seat on a train circling downtown on elevated tracks that have carried trains since 1897.
What it is
The elevated tracks that gave the Loop its name have carried trains around downtown since 1897: about 1.79 miles of steel on stilts above the streets, with eight stations. The ride is the cheapest sightseeing in the city. Quincy station, a block from Willis Tower, opened in 1897 and was renovated in the 1980s to look much as it did then.
How to do it
Board a Brown Line train heading into the Loop and sit by a window: it circles the outer track counterclockwise before turning back north. In 2026 a ride costs $2.50, paid by tapping a contactless card or phone at the gate, with up to two free transfers within two hours, and a 1-day pass costs $5.
Good to know
Get off at Quincy: you can look round the platform and board the next train without paying again.
Ride the Centennial Wheel and sail Lake Michigan from Navy Pier
Navy Pier, 600 East Grand Avenue
Half a dayBook ahead
Turn three times on a 196-foot wheel with the skyline in front of you, then sail Lake Michigan on a four-masted schooner.
What it is
Navy Pier opened in 1916 and runs about 3,300 feet into Lake Michigan from 600 East Grand Avenue; entry is free all year. The Centennial Wheel, 196 feet high, turns three times in a 12-minute ride with the skyline in front of you. To get out on the lake, the Tall Ship Windy is a 148-foot four-masted schooner on the south dock, and Seadog speedboats run past Buckingham Fountain and Museum Campus.
How to do it
In 2026 the Windy sailed Wednesday to Sunday at 1, 3, 5 and 7 pm until 27 September, so check the 2027 season first. CTA buses 29, 65, 66 and 124 stop at the pier, and water taxis run from May to September.
Good to know
In summer, free fireworks go off over the lake on Wednesdays at 9 pm and Saturdays at 10 pm, from late May to early September.
Time needed
Half a day
Best time
A summer Wednesday or Saturday night, for the fireworks
Sketches, improv and live music on the stage that trained Bill Murray, Tina Fey, Steve Carell and Stephen Colbert.
What it is
The Second City staged its first revue on 16 December 1959, and its Chicago stages trained Bill Murray, John Belushi, John Candy, Mike Myers, Steve Carell, Tina Fey, Amy Poehler and Stephen Colbert. Since 1967 it has played from 1616 North Wells Street. The show to see is the Mainstage revue, in 2026 the 114th, Pandemonium, Please Hold: sketches, improv and live music from a six-person cast. The smaller e.t.c. Theater stages other shows.
How to do it
It runs 120 minutes with a 15-minute interval, and seating opens 45 minutes before. Tickets start at $40, and the theatre serves small bites and local craft beers. Parking is at Piper's Alley Self Park, 230 West North Avenue, and is not validated.
Good to know
It is rated R for language, for ages 13 and up, minors with an adult.
Order the Chicago Classic deep dish at Lou Malnati's
Chicago, Illinois
1 to 1.5 hoursBook ahead
Deep dish from a recipe traced back to 1943: sausage, extra cheese and tomato sauce on a flaky, buttery crust, eaten with knife and fork.
What it is
Lou Malnati's has been making deep dish since 1971, when the first pizzeria opened in suburban Lincolnwood, and the family traces the recipe back to 1943 and Chicago's first deep-dish pizzeria. The pizza to order is the Malnati Chicago Classic: lean sausage, extra cheese and tomato sauce on the chain's Buttercrust, a flaky, buttery base. The thin crust is good too, but nobody comes for it.
How to do it
Today it has branches all over the city, including downtown. Lou's takes reservations through its website, worth doing for a weekend evening downtown. Deep dish is baked to order and takes a while, so order as soon as you sit down, or order ahead online and collect it.
Good to know
Eat it with a knife and fork, and give it a few minutes on the plate, because the cheese arrives molten.
O'Hare (ORD) is linked to the Loop by the CTA Blue Line, which runs 24 hours a day; the fare from O'Hare is $5, or nothing extra with an unlimited pass. Midway (MDW), 11 miles from downtown, is on the Orange Line at the normal $2.50 fare. Taxis, Uber and Lyft pick up at both airports. Amtrak trains from across the country arrive at Union Station, opened in 1925 just west of the Loop, which also serves the Metra commuter lines.
Getting around
Downtown is walkable and laid out on a grid: addresses count out from State and Madison streets, eight blocks to the mile. The 'L' does the rest. Tap a contactless card or phone at the gate: a ride costs $2.50, with up to two free transfers within two hours, and passes cost $5 for one day, $15 for three and $20 for seven. Divvy bikes and two water taxi services, Wendella's and Shoreline's, link the river, Museum Campus and Navy Pier.
How many days
In must30's view, four days is right for a first visit: one for the Loop, Millennium Park, the Art Institute and the 'L', one for the lakefront by bike with the Field Museum and Navy Pier, one for Oak Park, and one for the North Side, Wrigley Field and the clubs. Evenings go to the blues, comedy or deep dish. With a weekend, keep to the Loop and the lakefront.
When to go
Late May to September is the high season: summer temperatures average 78 to 92°F (26 to 33°C), cooler by the lake, Millennium Park hosts free concerts and Navy Pier fires its fireworks twice a week. April runs in the 50s°F (10 to 15°C) and May reaches about 70°F (21°C). October is usually the driest month and still mild. Winters are cold, with daily highs of 30 to 38°F (-1 to 3°C) and about 37 inches of snow a year, but the museums, the clubs and the Millennium Park ice rink carry on.
Where to base yourself
The Loop puts you between the 'L', the Art Institute and Millennium Park, and close to Union Station, but it is quiet at night. River North, just across the river, has many hotels and restaurants within walking distance of Michigan Avenue and Navy Pier. Lincoln Park and Lakeview, on the Red and Brown lines, are calmer, near the lake and close to Kingston Mines, Second City and Wrigley Field.
Questions travellers ask
How do you get from O'Hare to downtown Chicago?
Take the CTA Blue Line, which runs 24 hours a day from the airport to the Loop. The fare from O'Hare is $5, paid at the gate with a Ventra card or a contactless bank card, and an unlimited pass covers it at no extra cost. Taxis and ride-hail cars use marked pick-up points.
What are the best free things to do in Chicago?
Millennium Park, with Cloud Gate and the summer concerts at the Pritzker Pavilion, Navy Pier with its summer fireworks, and the 18-mile Lakefront Trail are all free. Buddy Guy's Legends plays a free acoustic dinner set most evenings it is open, and Illinois residents get free days at the big museums.
How many days do you need in Chicago?
In must30's view, four: two for the Loop, the museums and the lakefront, one for Oak Park, and one for the North Side, Wrigley Field and the clubs. A weekend covers the Loop and the lake.
When is the best time to visit Chicago?
Late May to September for the beaches, outdoor concerts and fireworks, or early October for mild and usually dry days. Winters are cold and snowy, with highs around freezing, but the museums, blues clubs and theatres keep going.
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