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Chicago Tours and Cruises

Chicago Tours

Enjoy a wide variety of sightseeing Chicago tours and Chicago cruises. Chicago is a world-class city of unsurpassed beauty, attracting visitors from around the nation and the world.  Chicago is home to the Blues, top sports teams, an internationally-renowned symphony orchestra, spectacular live theater, celebrated architecture, thousands of restaurants, and world-class museums and shops.  

Chicago Mother's Day Tour Gift Certificates

Our most popular tours are the Architectural Tours by Boat and the Chicago Trolley Tour. We also feature exceptional Dinner Cruises, as well as dinner show tickets and bus tours. Chicago Tours features a variety of bus tours, bike tours, Segway tours, shopping and food tours, and boat tours to show you the great sights of the great city of Chicago. See the Willis Tower, enjoy a fabulous Dinner Show, Rent a Bike or enjoy a Ghost Tour.

Featured Tours and Activities

Explore Chicago Hop On Hop Off Trolley Tour Image
Location: Chicago Duration: valid for 3 days
Voted Chicago's Best Tour, this Hop On Hop Off Trolley Tour has long been the gold standard for touring downtown Chicago. The tour gives you transportation to the most famous Chicago attractions on Red & Green Trolleys and Big Red Double Decker Buses. The Explore Tour allows you to hop off to visit a Chicago attraction or museum, shop, dine, and just explore as you have 3 full days to use it. With the same ticket, you also get seasonal access to three Neighborhood Tours (North, West and South – running May through September). Your tour can begin at any of the 14 stops in the downtown area. Stops include: Millennium Park, the Art Institute, Field Museum, Navy Pier, John Hancock Observatory, Skydeck Chicago, and the River North district, among many others. Take your time and hop-on/hop-off for three days!
From: $34.95 US Dollars
Chicago Architectural Cruise - 1 to 19 Persons - Weekdays Image
Location: Chicago Duration: 75 minutes
Enjoy a 75-minute cruise of the historic Chicago River that showcases over 40 landmarks of modern American architecture. Join us on an exciting journey as we tour the Chicago River and its architectural landmarks.
From: $31.70 US Dollars
Chicago Mini-Bus Tour Image
Location: Chicago Duration: 2 hours 15 min
This award winning city tour takes you on an entertaining, narrated journey around the downtown area and through several of Chicago's distinct neighborhoods. Along the way, you will be able to get out at several picturesque stops and take some wonderful photos. Comfortable, climate controlled, large windowed mini buses allow you to ride in style. This tour also includes complimentary pick-up from most downtown hotels. MINIMUM ORDER OF TWO PERSONS.
From: $39.95 US Dollars
Chicago Hop On & Hop Off Trolley Tours Image
Location: Chicago Duration: 90 minutes to 6 hours (you determine the total time)
Take a sightseeing hop on and hop off trolley tour in Chicago, Illinois. The trolley tour of the Windy City provides a comprehensive tour of Chicago, and you may hop on and hop off at a number of popular locations.
From: $29.95 US Dollars
Discover Chicago Segway Tour Image
Location: Chicago Duration: 3 Hours
This Segway Tour is perfect for both those new to the city and Chicago veterans. For the beginners, this tour will offer you a fantastic orientation and give you an opportunity to see virtually all of the sites you know from movies, postcards and history. For the veterans, you'll learn new facts and stories about Chicago that you've never heard. After taking this tour, you'll agree that Segway-ing is the best way to see the Windy City!
From: $69.95 US Dollars
Chicago Dinner Cruise - Friday Image
Location: Chicago Duration: 3 hours
The Chicago Dinner Cruise is a celebrated 3-hour dinner/dance cruise along the magnificent Chicago waterfront. Why go to a land-based restaurant when you can get so much more on our exciting cruise? Enjoy a Grande Buffet meal with an energetic interactive emcee to entertain you with the perfect vibe. Dance, relax and stroll under a canopy of stars. And for the most magnificent view of Chicago's skyline, simply look out any window.
From: $122.21 US Dollars
Chicago Grand Tour with Hancock Tower Image
Location: Chicago Duration: 5 1/2 hours
Enjoy the Chicago Grand Tour (a comprehensive tour of the major sights in Chicago) plus a visit to the 94th Floor Observatory at the Hancock Tower.
From: $59.95 US Dollars
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