Choosing a Tour of Chicago

Helicopter Ride

Chicago Helicopter Ride IL

Chicago Interactive Map

Sunset Cruise

Chicago Sunset Cruise Illinois

Chicago Boat Tours

Looking for a new view of Chicago?

Hop on one of these cruises and tour the Windy City on water when you go about choosing a tour of Chicago.

  • Odyssey Cruises: This 2-3 hour tour in Chicago is offered year round and has lakefront sightseeing and dining along with live entertainment and more. Tickets for this fun tour in Chicago typically run anywhere from $46 to $168 a person. These tours of Chicago all leave from Navy Pier.
  • Wendella Boats: If you are choosing a tour of Chicago, check out the Wendella Boats. You'll be glad that you did since you'll have the opportunity to be on a tour in Chicago that offer some of the most breathtaking views of the city. The tour runs 1-2 hours in length, is a sunset cruise, and tickets often run between $22 -$25.
  • Anita Dee: For fun tours of Chicago, check out the lakefront sightseeing offered by Anita Dee. These tours run for about 45 minutes and cost $15- $25 a person. They depart from Navy Pier and run between April and October. Come check out this entertaining tour in Chicago. 

Food Tours in Chicago

Check out the list of food tours below and you'll be able to snack your way through the city of Chicago. Enjoy these food tours of Chicago next time you're visiting the Windy City.
  • Gold Cost Tour/Millennium Loop : Ever wanted to eat your way through a city? Well, when choosing a tour in Chicago, head for this food tour, and you'll be able to do just that. The Gold Coast food tour occurs year-round and often occurs daily. This tour is certainly fun for the whole family and you'll be able to wander the city stopping at various popular food hot spots and Chicago restaurants. In a city with such phenomenal food, you're bound to have a delicious time. Not to mention, the tour only costs around $44!
  • Bikes, Bites, & Brews: For just $45-$60, you can stop by local Chicago eateries between 11:00am and 3:00pm Monday to Friday and enjoy a delectable sampling of cupcakes, pizza, hot dogs, and local beers.  When choosing a tour in Chicago, check this one out for sure and your taste buds will be singing!
  • Chicago Chocolate Tours: Chocoholic? No problem! Check out this absolutely sweet and delicious tour of Chicago and love every minute of it finding new chocolate treats! For $40, you can walk around the Windy City year round and enjoy tasty desserts.

Air Tours Chicago

Soar through the Windy City skies tonight when you go about choosing a tour of Chicago. You'll be sure to enjoy tours of Chicago in the sky as you will have the opportunity to see everything.
  • Chicago Flightseeing Tour: When on the flightseeing tour, you'll be able to catch great views of the Windy City from on high. Enjoy learning how to fly, roughly an hour of flying time, and a multi-course meal that is included in your flight package. When choosing a tour of Chicago, be sure to check this one out! 
  • Chicago Helicopter Rides: Looking for a tour in Chicago? Why not go for helicopter ride? You'll beat the traffic of the city and be able to see all of the major sights like Millennium Park, the entire skyline, and Lake Michigan. When checking tours in Chicago, head out to this one, and love the view from above.
  • Chicago Air Tours: Leaving from Schaumburt Airport, Jetway Aviation, is a Chicago based company that provides the largest aerial tour network.  They provide both day and night time flights in helicopters and airplanes. Embark on a on of these tours in Chicago and start to soar.
Chicago Travel Info
  Venue Info Price
Chicago Line Cruises
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Chicago Private Yacht Rentals
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Vertiport VIP Helicopter Tours
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Lakefront Bicycle Tour
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Adult Price

City Lights at Night Bike Tour
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Bikes, Bites & Brews Tour
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Adult Price

Bobby's Tike Hike
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Adult Price

Southside Gangster Bike Tour
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Museums at Sunset Bicycle Tour
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Adult Price

Chicago Favorites Food Tour

Adult Price


When visiting the Windy City, enjoy a variety of tours. Choosing a tour of Chicago can be a fun prospect when there are a variety of great options.

Enjoy everything from Chicago food tours to air tours of Chicago. There are tons of ways to see Chicago, and all of them provide different degrees of excitement, history, insight and more! You'll be happy you chose to tour the city by boat, plane, or food, if not by Segway, walking, or bike.

Have fun choosing a Chicago tour! If you don't think you can choose just one though, go one several! With Chicago tour deals, you can often find great prices on different tours of the city so that you can afford to do more!

If you already took your Chicago tour and saw some attractions, museums and Chicago sights that you want to explore up close, browse through our Chicago attraction discounts so that you can save on those as well! You don't have to pay full price to see this city, and when you're exploring the city with Chicago Traveler, you can always afford to do a few more to the best things to do in Chicago!