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Chicago Sightseeing & Tour Packages

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As a city world-renowned for architectural innovation, there’s no shortage of striking landmarks in Chicago. The Windy City is made for sightseeing – whether you’re experiencing the bright lights of downtown from above or soaking up the skyline by boat tour. Save money on your city tour packages and passes when you reserve your deal through us.

Chicago Sightseeing & Tours Reviews

Great experience! The staff are friendly, and the views are amazing. I recommend doing this at night.

Chicago Helicopter Experience

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The entire experience was great. Our guide was funny and full of so much Chicago knowledge, even my three kids under 12 sat still the whole ride! I highly recommend.

Tours and Boats

Great tour of Chicago north. Bus had roll-up windows and the weather was beautiful for taking pictures of the buildings and places of interest the knowledgeable driver pointed out.

Gray Line Chicago


 

Pro Tip: Some of the most popular Chicago tours take place around the Loop – its central business district. When the tour has finished, use the opportunity to do some sightseeing of your own. Travel the Red and Blue Lines to visit the city’s most bustling neighborhoods. We’d recommend sampling Pilsen’s arts and food scene.


 


Top Rated

Chicago Tour Packages: Frequently Asked Questions

From towering abstract art to picturesque piers, Chicago has a variety of sights to appreciate. Rediscover your favorite landmarks and find somewhere new to explore with these frequently asked questions. The Groupon Manual is the place to go for city tour package deal info and payment queries.

What type of local tours are available in downtown Chicago?

The Loop is the best place to start your tour of Chicago. Here you can explore the city in some pretty quirky ways, including by walking, bus or Segway.

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Some of our favorite downtown tours include:

  • Sunset Segway Tour. Embark on a guided Segway tour through Grant Park and Chicago Riverwalk to catch the sun setting over the river.
  • Chicago Crime Tour. Fancy yourself a detective? Explore the city's famous crime scenes on this sightseeing bus.
  • Scavenger Hunt Adventure. Follow the clues scattered around downtown as a team, with fun trivia, snapshot opportunities and compass challenges.

Where can I buy a city tour package in Chicago?

Buy a cheap city tour package online at Groupon to save up to 70% on sightseeing passes.

Whether you're a fully-fledged local or new to the city, our tour package deals will reveal a new side to the Windy City.

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Explore the city on foot, bus, boat, helicopter – and don't forget, deep-dish pizza is as much a part of the Chicago experience. For more great deals and ideas, take a look at our guide to the top 10 things to do in Chicago.

Which Chicago river tour is best?

Some of the most highly rated river tours in Chicago include the Tall Ship Windy, Chicago Cruise Events and the Seadog Lakefront Speedboat Tour.

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  • Tall Ship Windy. Learn about Chicago's architecture on this majestic sailing boat. Choose between an evening or daytime sail.
  • Chicago Cruise Events. Take in the city's skyline at night aboard a luxury yacht. Enjoy the fireworks, watch the sunset or soak up the views with a refreshing cocktail.
  • Seadog Lakefront Speedboat Tour. Short on time? Catch all of Chicago's top landmarks in 30 minutes with this speedboat tour.

Which neighborhoods should I visit in Chicago?

Chicago has an abundance of neighborhoods, all with their own culture, history and attractions. Pilsen, Hyde Park and Wicker Park are some of the best for food and culture.

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  • Pilsen is in the south-west of Chicago. Here you can soak up the colorful street art or catch a local act at Thalia Hall.
  • Hyde Park is just south of downtown and is home to the University of Chicago campus. If you're there in summer, head to 57th Street Beach.
  • Wicker Park is in the north-west and has been nicknamed Chicago's hip neighborhood. Head here on an evening to enjoy the abundance of bars, clubs and music venues.

More Sightseeing & Tours Deals

Wednesday Fireworks & Sunset Cruise or Thursday Sunset Cruise for One, Two, or Four (Up to 65% Off).
Up to 65% Off Sunset Cruises at Chicago Cruise Events
200 North Breakwater Access, Chicago3.2 mi
4.3
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2,237 Ratings
$32.00 $14.00$11.20
 Sale Ends 5/18
Wednesday Night Fireworks or Thursday Night Sunset Cocktail Cruise for One
Historical and Architectural Boat Tour for One, Two, or Four from Chicago Fireboat Tours (Up to 52% Off).
Up to 52% Off Boat Tour from Chicago Fireboat Tours
111 North Lake Shore Drive, Chicago3.1 mi
4.8
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482 Ratings
$40.00 $29.00$23.20
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Historical and Architectural Boat Tour for One
90-Minute Chicago Architecture Boat Tour One, Two, Three, or Four (Up to 40% Off)
Up to 40% Off 90-Min Chicago Architecture Boat Tour
900 South Wells Street, Chicago1.7 mi
4.7
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4,001 Ratings
$49.00 $29.00
40% discount_off
90-Minute Chicago Architecture Boat Tour for One
General Admission to Petting Farm for Up to Four People at Green Meadows Petting Farm (Up to 40% Off)
Up to 40% Off Admission to Green Meadows Petting Farm
33603 High Dr., East Troy
4.9
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11,269 Ratings
$14.00 $12.00$9.60
 Sale Ends 5/18
Petting-Farm General Admission for One
Navy Pier Skyline Segway Tour for One or Two at Bike and Roll Chicago (Up to 60% Off)
Up to 60% Off Navy Pier Segway Tour at Bike and Roll Chicago
700 E Grand Avenue, Chicago3.6 mi
4.8
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1,671 Ratings
$75.00 $39.00$31.20
 Sale Ends 5/18
Navy Pier Skyline Segway Tour for One; Valid Through 10/31/2022
Chicago C3 CityPASS Tickets for Adults and Children
Chicago C3 Ticket by CityPASS
6 Locations2.1 mi
4.8
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21 Ratings
$81.00
Chicago CityPASS C3 Tickets
Wednesday or Sunday Distillery Tour and Appetizer for One, Two, or Four at Koval Distillery 54% Off
Up to 54% Off on Distillery Tour at Koval Distillery
4241 North Ravenswood Ave., Chicago7.6 mi
4.7
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847 Ratings
$24.00 $16.00$12.80
 Sale Ends 5/18
Distillery Tour and One Breads and Spreads Appetizer for One Person
$20.80 for Two-Hour Walking Tour from Gangsters and Ghosts Tour ($32.92 Value)
36% Off Two-Hour Tour from Gangsters and Ghosts Tour
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4.7
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805 Ratings
$32.92 $26.00$20.80
 Sale Ends 5/18
Two-Hour Gangsters and Ghosts Tour for One
$19 for Toward Cruise at Chicago Party Boat
36% Off Booze Cruise with Chicago Party Boat
1559 South Lake Shore Drive, Chicago2.1 mi
3.9
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1,318 Ratings
$30.00 $19.00
36% discount_off
$30 Toward Cruise
$34 for Scavenger Hunt Adventure for Team of Up to Five People from Urban Adventure Quest ($49 Value)
30% Off Scavenger Hunt from Urban Adventure Quest
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4.6
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456 Ratings
$49.00 $36.50$34.00
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$36.50 for a Scavenger Hunt Adventure for One Team of Up to Five People
Monday or Tuesday Night Sunset Cruise for 1, 2, or 4 (Up to 70% Off).
Up to 70% Off Monday or Tuesday Night Sunset Cruise
200 North Breakwater Access, Chicago3.2 mi
4.3
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2,237 Ratings
$32.00 $12.00$9.60
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Monday or Tuesday Night Sunset Skyline Cruise for One
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