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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.
Anita Dee Yacht Charters
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Adult Price

$27
Details
2.
Chicago Elevated Walking Tours
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Adult Price

$20
Details
3.
Tall Ship Adventures
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Adult Price

$25
Details
4.
Interior Architecture Tour
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Adult Price

$26
Details
5.
Historic Chicago Bar Walking
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Adult Price

$32
Details
6.
See It All! Mini Bus Tours
offoffoffGrant ParkCulturalFamily FriendlyHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$39
Details
4.375
2 Reviews
7.
Adventure Sea Tours
offoffoffoffoffFamily FriendlyHistoricoffoffoffSights of ChicagoRomanticScenicoffoffoff

Adult Price

$43
Details
8.
Hancock Center
offoffoffoffCulturalFamily FriendlyHistoricoffMuseumoffSights of ChicagoRomanticScenicShoppingoffoff

Adult Price

$18
Details
9.
Gray Line Tours
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Adult Price

$30
Details
10.
Red Witch Tall Ship
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Adult Price

$95
Details

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!