Chicago · Illinois, USA
Things to Do in Chicago: Tours, Tickets & Day Trips
The best things to do in Chicago, ranked by real traveller reviews: ride the architecture river cruise, step onto the glass Ledge 1,353 feet up the Willis Tower, walk Millennium Park and the Bean for free, eat deep-dish on a food tour and follow Al Capone on a gangster bus. Compare 520+ tours, tickets and day trips side by side — most with free cancellation.
524 experiences Free cancellation Top-rated tours Instant booking
Sunset tours in Chicago
Departures that are under way when the sun sets in the coming weeks — start times checked against the local sunset.
Good for families in Chicago
Children can join from a young age and pay less than adults — taken from each operator’s price list.
Browse
Explore Chicago by interest
Whatever brings you to Chicago — world-class museums, the river, or a long lunch — start with the experiences travellers love most.
What to see
Top attractions in Chicago
The landmarks that define the city — and the tickets and tours that get you in, often skipping the line.
Chicago River
Architecture cruise.
160+ toursView tours
Willis Tower
Skydeck Ledge.
90 toursView tours
The Bean
Millennium Park.
110 toursView tours
360 Chicago
TILT deck.
80 toursView tours
Deep-Dish Pizza
Food tours.
80 toursView tours
Lake Michigan
Lakefront cruises.
70 toursView tours
Gangster Sites
Capone history.
60 toursView tours
Magnificent Mile
Shopping & sights.
70 toursView tours
1 day
Chicago in 1 day
- 1Architecture cruise
- 2Millennium Park
- 3Willis Tower
- 4Deep-dish dinner
3 days
Chicago in 3 days
- 1Day 1: river & skyline
- 2Day 2: museums
- 3Day 3: food & history
- 4Lakefront
For foodies
Chicago for foodies
- 1Deep-dish pizza
- 2Italian beef
- 3Chinatown tour
- 4Neighbourhood eats
Architecture cruise
Chicago architecture cruise
- 1Architecture river cruise on the Chicago River
- 2Willis Tower Skydeck or 360 Chicago
- 3Lake Michigan skyline cruise
- 4Sunset walk along the Riverwalk
Gangsters & crime
Chicago gangsters & crime
- 1Al Capone & mob bus tour
- 2Prohibition & speakeasy history
- 3Haunted Chicago after dark
- 4River North & the Loop on foot
20 min by L train awayOak Park
Frank Lloyd Wright Home & Studio.
from $24View trips
90 min by Amtrak awayMilwaukee
Breweries & the lakefront.
from $41View trips
1 hr by South Shore Line awayIndiana Dunes
Beaches & dune hikes.
from $18View trips
Lakefront, downtown awayNavy Pier
Centennial Wheel & boat departures.
from $30View trips
3 hrs by car awayGalena
Historic main street & food tour.
from $76View trips
From Navy Pier awayLake Michigan
Skyline & sunset cruises.
from $40View trips
Practical guide
Know before you go
Short, straight answers to the questions every Chicago visitor asks before booking.
Summer (Jun–Aug)
The peak season, warm and lively with festivals, lakefront fun, boat cruises and the best weather.
Autumn (Sep–Oct)
A beautiful time, with mild days, fall colours and thinner crowds, ideal for sightseeing.
Winter (Nov–Mar)
Cold and snowy with biting lake winds, but festive lights, indoor museums and lower prices.
Spring (Apr–May)
Cool and fresh as the city reawakens, with blossom and patios returning, though weather is changeable.
Cruise season
Architecture and lake cruises run mainly spring to autumn, when the weather is warmest.
Festival summer
Summer brings major festivals and events — book accommodation and tours early.
One day
The cruise, the Bean and the Skydeck.
Two days
Add a food tour and the museums.
Three days
Add history tours and the lakefront.
Culture lovers
More time at the Art Institute and museums.
Foodies
Add neighbourhood and Chinatown food tours.
With kids
Mix museums, decks and Navy Pier.
The "L" train
Chicago’s elevated "L" train is fast and cheap; a Ventra card covers trains and buses.
Tours & buses
Hop-on buses and walking tours are great for reaching the main sights downtown.
Walking & biking
Downtown, the Riverwalk and lakefront are very walkable, with Divvy bikes for longer hops.
Water taxi
River water taxis are a scenic way to travel between downtown landmarks in season.
Central base
Staying in the Loop or near the Magnificent Mile keeps sights and transit close.
Getting there
O’Hare and Midway airports both connect to downtown by the "L" train.
US dollars
Chicago uses the US dollar; cards are accepted everywhere and tipping (15–20%) is customary.
Book cruises ahead
The popular architecture river cruise sells out, especially in summer — reserve in advance.
Consider a CityPASS
If visiting several attractions, a CityPASS bundle can save money on top sights.
Dress for the weather
Summers are warm but winters are very cold and windy off the lake — pack accordingly.
Get a Ventra card
A Ventra card or contactless payment makes the "L" and buses easy to use.
Eat like a local
Don’t miss deep-dish pizza, an Italian beef and a Chicago-style hot dog.
Architecture cruise
The top experience sells out in summer — book ahead.
Observation decks
Skip queues with advance Skydeck and 360 tickets.
Food tours
Small-group food tours have limited spots — reserve early.
Helicopter tours
Limited flight slots fill quickly — book ahead.
Gangster tours
Popular history tours sell out — reserve early.
Museum entry
Buy timed tickets ahead for the top museums in peak season.
Architecture cruise
Around $45–60 for a 75–90 minute river cruise.
Observation deck
About $30–50 for the Skydeck or 360 Chicago.
Hop-on bus
Roughly $40–60 for a day of hop-on sightseeing.
Food tour
Around $60–100 for a guided food walking tour.
Helicopter tour
About $200–400 for a skyline helicopter flight.
How to save
Use a CityPASS, ride the "L" and book combos.
When to visit
Chicago through the seasons
What's best, how busy it gets, and one booking tip for each time of year.
Spring (Apr–May)
Apr–May
- Best for
- Fresh, blossom.
- Crowds
- Booking tip
- Changeable.
Summer (Jun–Aug)
Jun–Aug
- Best for
- Festivals, cruises.
- Crowds
- Booking tip
- Peak & busy.
Autumn (Sep–Oct)
Sep–Oct
- Best for
- Fall colours.
- Crowds
- Booking tip
- Lovely time.
Winter (Nov–Mar)
Nov–Mar
- Best for
- Lights, museums.
- Crowds
- Booking tip
- Cold & windy.
People also ask
Chicago travel FAQ
What are the top 10 things to do in Chicago?
Ranked by traveller reviews: 1) the Chicago Architecture River Cruise, 2) the Willis Tower Skydeck and its glass Ledge on the 103rd floor, 3) 360 Chicago with the TILT platform, 4) Millennium Park and Cloud Gate, 5) the Art Institute of Chicago, 6) a deep-dish and Italian-beef food tour, 7) the Crime and Mob bus tour, 8) a Lake Michigan skyline or sunset cruise, 9) Navy Pier and the Centennial Wheel, 10) the Field Museum and Shedd Aquarium on the Museum Campus.
How many days do you need in Chicago?
Plan two to three days. One day is enough for the river cruise, an observation deck and Millennium Park; a second day covers the Museum Campus or the Art Institute; a third adds a food tour, a gangster history tour and the lakefront. Four days or more let you add Wrigley Field, neighbourhoods like Pilsen and Wicker Park, or a day trip to Oak Park or Milwaukee.
What to do in Chicago for free?
Millennium Park and the Bean, the Chicago Riverwalk, the 18-mile Lakefront Trail and beaches, Lincoln Park Zoo, the Chicago Cultural Center, Garfield Park Conservatory, Buckingham Fountain, the 606 elevated trail and strolling Navy Pier are all free. In summer there are free concerts at the Pritzker Pavilion and fireworks at Navy Pier on Wednesday and Saturday nights.
What are the best day trips from Chicago?
Oak Park (20 minutes on the Green Line) for Frank Lloyd Wright’s Home & Studio, Milwaukee (90 minutes on Amtrak) for breweries and the lakefront, Indiana Dunes National Park (one hour on the South Shore Line) for beaches, and with a car Starved Rock State Park’s canyons or historic Galena. See our day trips page for bookable tours.
What to do in Chicago at night?
Take the architecture cruise at twilight, go up the Skydeck or 360 Chicago after dark, catch live blues at Buddy Guy’s Legends or Kingston Mines, see improv at The Second City, or join a ghost and gangster walking tour. In summer Navy Pier’s fireworks and the rooftop bars along the river round out the evening.
What is there to do in Chicago in winter?
Winter is museum season — the Art Institute, Field Museum, Shedd Aquarium and Museum of Science and Industry — plus the Skydeck, indoor food tours and gangster bus tours. From late November the Christkindlmarket fills Daley Plaza, the Millennium Park ice rink and Maggie Daley skating ribbon open, and Lincoln Park Zoo runs ZooLights. Architecture cruises pause from roughly late November to April.
What are the best things to do in Chicago with kids?
The Field Museum’s T. rex SUE, the Shedd Aquarium, the Museum of Science and Industry, the glass Ledge at the Skydeck, Navy Pier’s rides and the (free) Lincoln Park Zoo and Maggie Daley Park. An architecture cruise works for children from about age six; a Lake Michigan speedboat ride is a hit with older kids.
When is the best time to visit Chicago?
Late May to mid-October — warm weather, boat cruises running and the lakefront in full swing. September is the sweet spot with fewer crowds and mild days. Winter is very cold and windy but cheap, with festive lights and empty museums.
Is the architecture river cruise worth it?
Yes — it is consistently the highest-rated experience in Chicago with more than 16,000 reviews, and the only way to see the skyline the way it was designed to be seen, from the river. Book a few days ahead in summer.
524 Chicago experiencesfrom $30 · free cancellation
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