StayAreasThe best things to do in Chicago
Chicago's centre is the Loop, the grid of skyscrapers ringed by the elevated 'L' tracks, with Millennium Park and the Art Institute on its lake side. The Chicago River curls around its north and west edges; across it are River North's restaurants, the Magnificent Mile's shops and the Gold Coast's mansions by the lake. The West Loop's food scene and Wicker Park's bars are a short train ride west, and the Museum Campus sits on the lake just south of the Loop.
Here are the 20 things we'd put on a first trip, grouped by part of the city, with the area to stay in if that part of Chicago matters most to you. Summer and early autumn are the best time to visit, when the river boats run and the beaches are open; winters are long and very cold.
The Loop and the river
1.The architecture river cruise
A 75-minute boat ride along the Chicago River between the city's landmark skyscrapers, with a guide explaining how Chicago invented the tall building.
Tip: The Chicago Architecture Center's own cruise has the best guides. Boats run from spring to late autumn; take an evening sailing for the skyline lights.
Stay nearby: The Loop · ~$240/night2.Millennium Park and Cloud GateFree
The city's showpiece park, with Anish Kapoor's mirrored 'Bean', the Crown Fountain's video faces and Frank Gehry's Pritzker Pavilion.
Tip: The Grant Park Music Festival puts on free classical concerts at the Pritzker Pavilion on summer evenings.
Stay nearby: The Loop · ~$240/night3.The Art Institute of Chicago
One of the great art museums of the world, with Seurat's 'A Sunday on La Grande Jatte', Hopper's 'Nighthawks' and Grant Wood's 'American Gothic'.
Tip: It's closed on some weekdays, so check the days before you go. Head straight for the Impressionist galleries before they fill up.
Stay nearby: The Loop · ~$240/night4.The Chicago Cultural CenterFree
The city's grand former public library across from Millennium Park, with the world's largest Tiffany glass dome.
Tip: Entry is free, and there are free exhibitions and lunchtime concerts; the dome is on the third floor.
Stay nearby: The Loop · ~$240/night5.Skydeck at Willis Tower
The 103rd-floor observation deck of what was once the world's tallest building, with glass boxes called The Ledge sticking out from the wall.
Tip: Queues are longest in the afternoon. On a clear day you can see four states.
Stay nearby: The Loop · ~$240/night6.The Chicago RiverwalkFree
A promenade along the main branch of the river, below street level, with cafés, wine bars and kayak hire.
Tip: Walk it from Lake Street to the lake end on a summer evening, when the bars spill out onto the water.
Stay nearby: The Loop · ~$240/night7.The Field Museum and Shedd Aquarium
Two of the city's big museums on the Museum Campus by the lake: the Field has Sue, the most complete T. rex ever found, and the Shedd has beluga whales and a coral reef.
Tip: Walk out to the Adler Planetarium at the tip of the campus afterwards for the classic view of the skyline across the water.
Stay nearby: The Loop · ~$240/night
River North, the Magnificent Mile and the Gold Coast
8.Chicago deep-dish pizza
The city's own pizza, baked in a deep pan with the cheese under the tomato sauce. River North has several of the famous names.
Tip: A deep-dish takes around 45 minutes to bake; some places let you order while you wait for a table.
Stay nearby: River North · ~$260/night9.The Magnificent MileFree
The stretch of Michigan Avenue north of the river, lined with flagship stores and landmarks like the Wrigley Building and the Gothic Tribune Tower.
Tip: Start at the DuSable Bridge over the river and walk north to the old Water Tower, which survived the 1871 Great Fire.
Stay nearby: Magnificent Mile · ~$260/night10.360 Chicago
The observation deck on the 94th floor of 875 North Michigan, the old John Hancock Center, looking down the lakeshore.
Tip: Its view takes in the lake and the beaches, which the Skydeck doesn't. TILT tips you out over the street for an extra fee.
Stay nearby: Magnificent Mile · ~$260/night11.Navy Pier
A long pier out into Lake Michigan with a big Ferris wheel, boat tours and views back to the skyline.
Tip: In summer there are fireworks over the lake on some evenings; check the pier's calendar.
Stay nearby: Magnificent Mile · ~$260/night12.Oak Street and North Avenue beachesFree
City beaches on Lake Michigan right next to the Gold Coast's high-rises, linked by the 18-mile Lakefront Trail.
Tip: Hire a Divvy bike and ride the Lakefront Trail north to Lincoln Park; swimming is only allowed in summer when lifeguards are on duty.
Stay nearby: Gold Coast · ~$300/night13.Lincoln Park ZooFree
One of the oldest zoos in the country and one of the last free ones, with lions, gorillas and polar bears in a lakeside park.
Tip: Walk on to the Lincoln Park Conservatory next door, which is also free.
Stay nearby: Gold Coast · ~$300/night14.Second City
The improv comedy theatre in Old Town where Bill Murray, Tina Fey and Steve Carell started out.
Tip: Stay after the main show on some nights for a free improv set built on audience suggestions.
Stay nearby: Gold Coast · ~$300/night
West Loop and Wicker Park
15.Fulton Market and Randolph Street
Old meatpacking streets that became Chicago's restaurant row, with some of the most talked-about kitchens in the city.
Tip: Book the popular places weeks ahead for weekend dinners, or go for a weekday lunch.
Stay nearby: West Loop · ~$270/night16.Wicker Park and The 606Free
A neighbourhood of vintage shops, record stores, bars and music venues, crossed by The 606, an old railway line turned into a raised park trail.
Tip: Walk or cycle The 606 west from Wicker Park at sunset, then come back for dinner on Milwaukee Avenue.
Stay nearby: Wicker Park · ~$220/night
Further out
17.A Chicago blues club
Chicago's electric blues was born on the South Side; clubs like Kingston Mines in Lincoln Park and Buddy Guy's Legends in the South Loop still have live bands every night.
Tip: Kingston Mines has two stages and plays until very late; arrive early on weekends for a seat.
18.A Cubs game at Wrigley Field
Baseball in a 1914 ballpark with ivy-covered outfield walls, in the middle of the Wrigleyville bar district.
Tip: The season runs from April to September. The Red Line stops right outside at Addison.
19.Museum of Science and Industry
A huge science museum in Hyde Park with a captured German U-boat, a coal mine you go down into and a full-size Boeing 747.
Tip: Allow most of a day. The Metra Electric train from downtown stops a short walk away.
20.Garfield Park ConservatoryFree
One of the largest greenhouse conservatories in the US, with palms, ferns and a desert house under glass on the West Side.
Tip: Entry is free but you need to reserve a time online. It's a warm escape on a winter day.
Written by the StayAreas editorial team · Updated Oct 2026 · How we research our guides