Chicago Tours &
Things to Do
Discover the best Chicago tours and things to do in the Windy City: glide along the river on the famous architecture cruise, gaze down from the Willis Tower Skydeck and 360 Chicago, ride a hop-on bus past the Bean and Millennium Park, feast on deep-dish pizza on a food tour, and dig into the city’s gangster past. Compare top-rated experiences and plan your perfect Chicago trip.
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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.
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.
Willis Tower
Skydeck Ledge.
The Bean
Millennium Park.
360 Chicago
TILT deck.
Deep-Dish Pizza
Food tours.
Lake Michigan
Lakefront cruises.
Gangster Sites
Capone history.
Magnificent Mile
Shopping & sights.
Chicago in 1 day
- 1Architecture cruise
- 2Millennium Park
- 3Willis Tower
- 4Deep-dish dinner
Chicago in 3 days
- 1Day 1: river & skyline
- 2Day 2: museums
- 3Day 3: food & history
- 4Lakefront
Chicago for foodies
- 1Deep-dish pizza
- 2Italian beef
- 3Chinatown tour
- 4Neighbourhood eats
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
Chicago gangsters & crime
- 1Al Capone & mob bus tour
- 2Prohibition & speakeasy history
- 3Haunted Chicago after dark
- 4River North & the Loop on foot
Downtown awayChicago River
Architecture cruise.
Loop awayWillis Tower
Skydeck Ledge.
Downtown awayMillennium Park
"The Bean".
Citywide awayDeep-Dish Tour
Iconic pizza.
Citywide awayGangster Tour
Capone history.
Lakefront awayLake Michigan
Skyline cruise.
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.
Chicago through the seasons
What's best, how busy it gets, and one booking tip for each time of year.
- Best for
- Fresh, blossom.
- Crowds
- Booking tip
- Changeable.
- Best for
- Festivals, cruises.
- Crowds
- Booking tip
- Peak & busy.
- Best for
- Fall colours.
- Crowds
- Booking tip
- Lovely time.
- Best for
- Lights, museums.
- Crowds
- Booking tip
- Cold & windy.