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The Chicago Bucket List

Lakefront runs, deep-dish lunches, river architecture cruises at golden hour. The once-in-a-lifetime experiences that define a Chicago trip — the bucket-list tours and tickets worth planning around.

Chicago travel guide →3-day plan →Weekend in Chicago →

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Top experiences in Chicago

Bookable through GetYourGuide. Skip-the-line, verified guides.

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Explore Chicago's legendary architecture and history.
1h 30m

Chicago River 90-Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy...

  • Top-rated · 4.7★
  • Bestseller
From $45 a person
Daley Plaza Picasso
1h 30m

Chicago Walking Tour: Must-See Chicago

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art...

  • Top-rated · 4.9★
  • Free cancellation
From $35 a person
2h

Chicago Murder Mystery Tour

You will solve a murder as you learn real Chicago history!

  • Top-rated · 5.0★
  • Free cancellation
From $35 a person
2h

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Discover Chicago at your own pace with Big Bus.

  • Bestseller
  • Free cancellation
From $49 a person
Join us in the daytime or evening for City lights and breathtaking views
45 min

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire.

  • 4.7★ · 3360 reviews
  • Bestseller
From $28 a person
1h 30m

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture...

  • Top-rated · 4.9★
  • Bestseller
From $57 a person
This tour cruises the Chicago River and Lake Michigan.
1h 30m

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all.

  • 4.7★ · 2360 reviews
  • Bestseller
From $45 a person
Kid smiling faces say it all on our Family Friendly Chicago Food & Bike Tour. Ride a Bicycle, taste local favorites, and enjoy one of the best Kid-Friendly Things to do in Chicago.
4h

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today...

  • 4.8★ · 99 reviews
  • Free cancellation
From $79 a person
1h to 1h 30m

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River.

  • Top-rated · 4.8★
  • Bestseller
From $39 a person
216h

Chicago CityPASS®

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets.

  • Instant confirmation
From $144 a person
1h to 4h

360 CHICAGO Observation Deck Admission

The best views of Chicago can be yours at 360 Chicago Observation Deck!

  • Free cancellation
  • Instant confirmation
From $30 a person
Chicago Food Tour
2h

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider stories...

  • Top-rated · 4.8★
  • Free cancellation
From $87 a person
1h 30m

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides!

  • Top-rated · 4.8★
  • Bestseller
From $37 a person
Skyline Queen showcasing the Chicago Skyline!
1h 30m

Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline.

  • Top-rated · 4.7★
  • Free cancellation
From $46 a person
Photo Ops Off the Bus
1h 30m to 2h

Chicago Crime and Mob Bus Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus.

  • 4.6★ · 3408 reviews
  • Bestseller
From $49 a person
Segways are fun and easy to ride!
2h

Chicago Landmarks & Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago?

  • Top-rated · 5.0★
  • Free cancellation
From $70 a person
The Chicago River, as seen from our stop on wacky Wacker Drive
2h to 4h

Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city.

  • Top-rated · 4.8★
  • Free cancellation
From $50 a person
2h

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago.

  • Top-rated · 4.9★
  • Free cancellation
From $35 a person
2h

Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper!

  • Top-rated · 5.0★
  • Bestseller
From $35 a person
1h 30m

Chicago Sunset Tour by Open-Top Bus with Live Guide

Experience the magic of Chicago at dusk on a live-guided panoramic adventure that captures the city in its most captivating light.

  • Free cancellation
  • Instant confirmation
From $39 a person
30 min

Flyover in Chicago

The Flyover experience takes 30 minutes from beginning to end.

  • Top-rated · 4.7★
  • Free cancellation
From $28 a person
2h

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks.

  • Free cancellation
  • Instant confirmation
From $84 a person
1h 30m

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats.

  • 4.5★ · 1609 reviews
  • Bestseller
From $45 a person
1h 30m

Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise.

  • Free cancellation
  • Instant confirmation
From $57 a person

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