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Favorite Chicago Tours

The Best Tours in Chicago

When visiting a new city, it’s always a good idea to take a narrated tour to get your bearings and discover places you plan to return to for a closer look. Chicago offers a variety of sightseeing tours, some very general in nature such as a lakefront skyline boat tour and some very specific to unique interests such as one of Chicago’s fantastically tasty, interesting and fun Chicago food tours, a popular architecture tour that features over 40 historically significant Chicago landmarks, or a hop-on, hop-off trolley tour of the City.

There are a variety of bus and trolley tours to choose from, as well as bike, Segway and walking tours of the city that provide close-up experiences where you’ll learn about the unique Chicago neighborhoods and landmarks. There are so many great Chicago activities that it's hard to choose the most important ones, but all the best tours take you to the best places to see in Chicago, and skip the places and tourist traps that you can live without!
To do even more while you're here, be sure to check out all the Chicago deals on attractions, tours and more!

Chicago Food Tours

Chicago is famous for its fun and in depth food tours such as those offered by Chicago Food Planet Food Tours featuring guided neighborhood food-tasting tours of Old Town, Lincoln Park, Gold Coast, Bucktown/Wicker Park & Chinatown neighborhoods. Tastebud Food Tours offers a real taste of Chicago with famous Deep Dish Pizza, Chicago style hot dogs or Famous Italian Beef and much more in the magnificent downtown neighborhoods!

Chicago Dine-Around offers a unique and interactive dining tour that will create a memorable experience for your visit to Chicago, celebration or corporate event. The Progressive Dining Tour will escort you on a stylish coach bus to three different restaurants. En route to each restaurant you will be able to meet new people and learn about Chicago. Ideal for team-building, networking and all types of corporate events, guests have the opportunity to sit and interact with different colleagues at each restaurant.

The Bikes, Bites, and Brews tour is the most popular Chicago food tour offered by Bobby's Bike Hike, and it is definitely a highly recommended food tour in Chicago. You’ll sample from each of Chicago's four favorite food groups (pizza, hot dogs, cupcakes and beer) and have a difficult time not getting full!

Chicago Boat Tours

Chicago Boat Tours

Boat tours take you along the Lake Michigan shoreline, where you’ll learn about the different buildings set prominently along the Chicago skyline, or up the Chicago River for a wonderful architectural learning experience. Chicago is famous for it's beautiful architecture which for the most part has been rebuilt since the 1871 Great Chicago Fire.

The narrators typically provide interesting information about the history of Chicago and some of its most prominent past citizens and point out the beauty of the "Second City," accomplished by many famous architects. See Our Chicago Cruise Boat Comparison to find the best Chicago tour for you!

Some of the most popular boat tours in Chicago include the turbo charged Sea Dog Speedboat cruise, the trendy Mystic Blue cruise, the festive Spirit of Chicago cruise and the elegant Odyssey Cruise. Many of these boat tours and cruises highlight the city's beautiful architecture, history and beauty with witty and extremely knowledgeable hosts who won't let you miss a single thing!

Chicago Travel Info
  Venue Info Price
1.
Interior Architecture Tour
ActiveoffoffoffCulturalFamily FriendlyHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$26
Details
2.
Historic Chicago Bar Tour
ActiveoffoffoffCulturaloffHistoricoffoffNightlifeoffoffoffoffoffoff

Adult Price

$32
Details
3.
Interactive Culinary Events
offArtsyoffoffCulturalFamily FriendlyoffoffoffNightlifeoffoffoffoffoffoff

Adult Price

$65
Details
4.
Best Architecture Walking Tour
ActiveArtsyoffoffCulturaloffHistoricoffoffoffSights of Chicagooffoffoffoffoff

Adult Price

$22
Details
5.
Food Tours with Chicago Detour
ActiveoffoffoffCulturaloffHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$22
Details
6.
Adventure Sea Tours
offoffoffoffoffFamily FriendlyHistoricoffoffoffSights of ChicagoRomanticScenicoffoffoff

Adult Price

$43
Details
7.
360 Chicago
offoffoffoffCulturalFamily FriendlyHistoricoffMuseumoffSights of ChicagoRomanticScenicShoppingoffoff

Adult Price

$18
Details
8.
Bike and Roll Chicago
ActiveoffoffoffoffFamily FriendlyoffoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$10
Details
9.
Red Witch Tall Ship
ActiveoffoffoffoffFamily FriendlyoffoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$95
Details
10.
Downtown Deco
offArtsyoffoffCulturaloffHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$15
Details
11.
Hop On Hop Off Tour
ActiveArtsyoffoffCulturalFamily FriendlyHistoricoffMuseumoffSights of ChicagoRomanticScenicoffoffoff

Adult Price

$27
Details
12.
Chicago Grand Tour
offoffoffoffoffFamily FriendlyHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$50
Details
13.
Double Decker Hop On/Off
ActiveArtsyChicago Theater DistrictoffCulturalFamily FriendlyHistoricoffMuseumoffSights of ChicagoRomanticScenicoffoffoff

Adult Price

$33
Details
14.
North Side Tour
offoffoffoffoffFamily FriendlyoffoffoffoffSights of Chicagooffoffoffoffoff

Adult Price

$25
Details
15.
Segway Tour
ActiveArtsyoffoffCulturalFamily FriendlyHistoricoffMuseumoffSights of ChicagooffScenicoffoffoff

Adult Price

$70
Details
16.
Segway Night Tour
ActiveArtsyoffoffCulturalFamily FriendlyHistoricoffoffNightlifeSights of ChicagoRomanticScenicoffoffoff

Adult Price

$60
Details
17.
Chicago Shopping Tour
ActiveArtsyoffoffoffoffoffoffoffoffSights of ChicagooffScenicShoppingoffoff

Adult Price

$56
Details
18.
Chicago Skyscrapers Tour
ActiveoffoffoffoffoffHistoricoffoffoffSights of Chicagooffoffoffoffoff

Adult Price

$15
Details
19.
Chicago Outlets
offoffoffoffoffoffoffoffoffoffoffoffoffShoppingoffoff

Adult Price

$35
Details
20.
South Shore Tour
offoffoffGrant ParkoffFamily FriendlyHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$25
Details

Chicago Tour Tickets


    • Fall Happenings
    • SundayDec 16 Date TBA: Good for Any Sunday Through December 16, 2018 @ 2:00pm (Reserve in Advance)
    • Chicago Cocktail Crawl
      American Walks - Daley Center - Chicago
      Full Price: $120 | Our Price: $20 - $60

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    • Fall Happenings
    • SundayDec 16 Date TBA: Any Available Saturday at 4:00pm Through December 16, 2018 (Reserve in Advance)
    • Chicago Prohibition Tour
      American Walks - Franklin St. - Chicago
      Full Price: $25 | Our Price: $12.50

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    • Fall Happenings
    • SundayDec 16 Date TBA: Good Any Available Sunday at 11:00am or Thursday at 6:00pm Through December 16, 2018 (Reserve in Advance)
    • Sweet Chicago Dessert Walk
      American Walks - Daley Center - Chicago
      Full Price: $50 | Our Price: $20 - $25

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    • Comp Train
    • SaturdayDec 29 8:30pm (Boarding Begins at 7:45pm)
    • Eve of the Eve Cocktail Cruise
      Anita Dee II Yacht at DuSable Harbor - Chicago
      Full Price: $49 | Our Price: COMP - $25

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    • Fall Happenings
    • SundayDec 30 Date TBA: Good for Any Saturday at 11:00am, Sunday at 4:00pm or Thursday at 6:00pm Tour Through Dec. 30, 2018 (Reserve in Advance)
    • Chocolate, Cupcakes & Sweets Tour
      Water Tower Place - Chicago
      Full Price: $50 | Our Price: $20 - $25

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    • Tours & Cruises
    • MondayDec 31 Date TBA: Good Any Sat or Sun at 2:00pm Through Dec 30, 2018 (Reserve in Advance)
    • Chicago Pizza & Beer Tour
      American Walks - Daley Center - Chicago
      Full Price: $85 | Our Price: $20 - $42.50

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    • Holiday
    • MondayDec 31 10:30pm (Boarding Begins at 10:00pm)
    • New Year's Eve Fireworks Cruise
      Chicago Cruise Events at DuSable Harbor - Chicago
      Full Price: $175 | Our Price: $139

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    • Under $10
    • SaturdayJan 05 Date TBA: Any Available Saturday at 11:00am Through January 5, 2019 (Reserve in Advance)
    • Winter Chicago Architecture Tour
      American Walks - Clark Street Bridge - Chicago
      Full Price: $25 | Our Price: $10 - $12.50

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    • Make It a Date
    • SaturdayFeb 16 8:30pm
    • Cupid's Booze Cruise
      Anita Dee II Yacht at DuSable Harbor - Chicago
      Full Price: $50 | Our Price: $20 - $25

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    • Comp Train
    • SundayFeb 24 Date TBA: Any Available Saturday at 11:00am or Sunday at 1:00pm Through February 24, 2019 (Reserve in Advance)
    • Chicago Donuts & Sweets Walk
      American Walks - Chicago Ave. - Chicago
      Full Price: $50 | Our Price: COMP - $25

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    • Tours & Cruises
    • SundayFeb 24 Date TBA: Any Available Sunday at 3:30pm Through Feb. 24, 2019 (Reserve in Advance)
    • Winter Chicago Beer Crawl
      American Walks - Daley Center - Chicago
      Full Price: $85 | Our Price: $20 - $42.50

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    • Activities & Competitions
    • SundayFeb 24 Date TBA: Good Any Sunday at 2:00pm Through February 24, 2019 (Reserve in Advance)
    • Winter Neighborhood Wine Walk
      American Walks - Daley Center - Chicago
      Full Price: $120 | Our Price: $60

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    • Tours & Cruises
    • SaturdayMar 02 8:30pm-11:30pm (Boarding Begins at 7:45pm)
    • Mardi Gras Booze Cruise
      Anita Dee II Yacht at DuSable Harbor - Chicago
      Full Price: $50 | Our Price: $25

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    • Comp Train
    • SaturdayApr 27 Date TBA: Good for Any Saturday Through April 27, 2019 @ 4:00pm (Reserve in Advance)
    • Chicago Prohibition Tour
      American Walks - Franklin St. - Chicago
      Full Price: $25 | Our Price: COMP - $12.50

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    • Comp Train
    • SaturdayApr 27 Date TBA: Any Sat Tour at 4:00pm Through April 27, 2019
    • Chicago Sculpture & Art Tour
      American Walks - Chicago Cultural Center - Chicago
      Full Price: $25 | Our Price: COMP - $12.50

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    • Under $10
    • SaturdayApr 27 Date TBA: Good for Any Available Friday or Saturday Through April 27, 2019 at 7:00pm (Reserve in Advance)
    • Mobster & Crime Tour
      American Walks - Clark Street Bridge - Chicago
      Full Price: $25 | Our Price: $10 - $12.50

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    • Comp Train
    • SundayApr 28 Date TBA: Good for Any Available Date Through April 28, 2019
    • Chicago Cupcakes & Ice Cream Tour
      Water Tower Place - Chicago
      Full Price: $50 | Our Price: COMP - $25

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    • Comp Train
    • SundayApr 28 Date TBA: Any Available Saturday or Sunday Through April 28, 2019 at 1:00pm (Reserve in Advance)
    • Chicago Pizza Tour
      American Walks - Chicago Ave. - Chicago
      Full Price: $50 | Our Price: COMP - $25

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    • Comp Train
    • SundayApr 28 Date TBA: Good for Any Available Saturday or Sunday at 7:00pm Through April 28, 2019 (Reserve in Advance)
    • Chicago's Haunted History & Ghost Tour
      American Walks - Clark Street Bridge - Chicago
      Full Price: $25 | Our Price: COMP - $12.50

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    • Tours & Cruises
    • SundayApr 28 Date TBA: Any Available Saturday or Sunday Through April 28, 2019 at 1:00pm (Reserve in Advance)
    • Famous Chicago Food Walk
      American Walks - Chicago Cultural Center - Chicago
      Full Price: $50 | Our Price: $20 - $25

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    • Comp Train
    • SundayApr 28 Date TBA: Good for Any Sunday @ 11:00am or Thursday @ 6:00pm Tour Through April 28, 2019 (Reserve in Advance)
    • Sweet Chicago Dessert Walk
      American Walks - Daley Center - Chicago
      Full Price: $50 | Our Price: COMP - $25

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    • Tours & Cruises
    • SundayApr 28 Date TBA: Good for Any Sunday Through April 28, 2019 @ 2:00pm (Reserve in Advance)
    • Winter Chicago Cocktail Crawl
      American Walks - Daley Center - Chicago
      Full Price: $120 | Our Price: $48 - $60

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    • Comp Train
    • SundayApr 28 Date TBA: Good for Any Saturday at 11:00am, Sunday at 4:00pm or Thursday at 6:00pm Tour Through April 28, 2019 (Reserve in Advance)
    • Winter Chocolate, Cupcakes & Sweets Tour
      Water Tower Place - Chicago
      Full Price: $50 | Our Price: COMP - $25

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    • Tours & Cruises
    • SundayApr 28 Date TBA: Any Available Saturday or Sunday Through April 28, 2019 at 1:00pm (Reserve in Advance)
    • Wrigley Neighborhood Food Walk
      Wrigley Field - Chicago
      Full Price: $50 | Our Price: $20 - $25

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Don't Miss a Deal!

Be sure to check out all the current Chicago tour deals and discounts on top attractions in the city! You can find discounted rates, special savings and packages to save you big on some of the best things to do in Chicago! To save even more on your stay, check out all the Chicago hotel deals that will put you in the middle of all the action, so that you're closer to all the things you want to see, do and taste while you're here! Many hotels offer package deals that include discounted rates and fun Chicago activities to enjoy on your stay!

Top Tours in Chicago

Organized Chicago sightseeing tours are a fantastic way to make sure you see the “must” places, landmarks and attractions in Chicago. The best tours in Chicago are offered by local experts so you’ll waste little time and enjoy memorable experiences that will last a lifetime. Deciding on a Chicago tour can be a challenge – here are a few top tours in Chicago to choose from.

  • Walking tours around the different neighborhoods are one of the most popular Chicago Tours. These tours take guests into the heart of areas such as Greektown, Little Italy, and Gold Coast to explore the rich cultural heritage that each neighborhood offers.
  • Bike tours are a fun way to see all that Chicago has to offer. Whether it is by peddling using your own power, or zipping along on a Vespa-scooter, this tour of Chicago is a popular mode of transportation with people of all ages.
  • Carriage Tours are a unique way to travel around downtown Chicago. The horse and carriage mode of transportation are especially popular around the holidays when many carriage drivers dress up in period-attire
  • Segway Tours are perfect for those who like to try something a little different. This eco-friendly mode of transportation is a great way to see many of the top Chicago attractions.
  • Boat Tours are by far one of the most popular types of Chicago tours. Take an enjoyable ride aboard one of these boats and enjoy beautiful views of the Chicago skyline that you can't get practically any other way!
  • Sightseeing Cruises are an upgrade from boat tours, and offer a little more upscale traveling along the way. Dinner cruises are the most popular, but they also offer lunch and brunch cruises, and you can even book one for a special event!
  • Architecture Tours in Chicago take you around to show you all the best views and give you an entertaining rundown all the history that made the Second City what it is today! These tours are offered in all forms - whether you're looking to walk around, ride a bike or board a boat!