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United States · trip length

How Many Days in Chicago?

Lakefront runs, deep-dish lunches, river architecture cruises at golden hour. How long you actually need in Chicago — and the experiences to fill each day, whether you have a weekend or a week.

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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Amazing skyline and lakefront views await on our Chicago Bike Tour. Experience the city’s beauty up close on a Bicycle Tour in Chicago that blends culture, history, and unforgettable scenery.
3h

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour!

  • Top-rated · 4.9★
  • Free cancellation
From $59 a person
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
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
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
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
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
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
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
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
30 min to 1h 30m

Skydeck - Willis Tower Admission

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck.

  • Bestseller
  • Free cancellation
From $44 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
CloudBar
2h

360 Chicago Observation Deck Sip and View Ticket

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

  • Free cancellation
  • Instant confirmation
From $44 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 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
360 Chicago
24h to 120h

Chicago Attractions Pass: Save up to 50% - Includes 360 CHICAGO

Enjoy admission to more than 30 of Chicago's most popular attractions with Go City's All-Inclusive Pass.

  • Instant confirmation
From $149 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

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
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
Navy Pier 4 - Ride Pass
24h to 720h

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

Access top Chicago attractions, tours and activities with Go City's Explorer Pass.

  • Instant confirmation
From $84 a person
The Chicago Loop is the city's epicenter of culture, commerce, and design.
2h to 2h 30m

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown.

  • Free cancellation
  • Instant confirmation
From $10 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
1h 30m to 2h

Delicious Donuts & Sweet Treats: West Loop Walking Tour

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts.

  • 5.0★ · 74 reviews
  • Free cancellation
From $70 a person
45 min to 1h 30m

Museum of Illusions Chicago Admission Ticket

Step into the captivating realm of illusions, where reality is never exactly as it appears.

  • Instant confirmation
  • Short pick · ≤2h
From $43 a person
2h

Magnificent Mile Tour With Optional 360 Chicago Upgrade

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers.

  • 4.9★ · 81 reviews
  • Free cancellation
From $42 a person

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