Chicago Day Trips & Excursions
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
Taste all of Chicago’s classic eats on this four-hour guided bicycle tour!
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$77.99Chicago Segway Tour
Hop on the most innovative tour to hit Chicago in years!
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$70.85Frank Lloyd Wright by Bus Tour from Chicago
Discover the neighborhood where Wright's famed Prairie Style of architecture evolved.
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$55Cool Destinations VIP: Chicago Helicopter Tour Plus 360 Chicago Observation Deck
This combo ticket offers the best views of Chicago's world-famous skyline. You'll soar Chicago's 24 miles of shoreline on a guided helicopter flight that covers all of the city's famous landmarks and iconic skyscrapers. Then you'll ascend 94 stories to the observation deck of the John Hancock, one of the tallest buildings in North America, for a bird's eye view of the city below.
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$169.99Chicago Lakefront Neighborhoods Bicycle Tour
This is the tour that made Bobby famous!
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$47.99The Chicago Tour
This tour is an overview of what makes Chicago so fascinating-the neighborhoods, history, architecture, culture, and foods.
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$99Chicago Segway Tour and Skydeck Admission
Experience Chicago in two great ways - by segway and its best vantage point. This combo ticket allows you to experience a Chicago Segway tour and also gain entry to Skydeck, the observation deck at Willis Tower. Skydeck tickets are valid for 6 months from the purchase date listed on your voucher, and you are not required to visit at a specific time.
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$90.47Land and River Architecture Tour of Chicago's Scenic North Side
This tour will take you past all the sights of Chicago’s Scenic North Side.
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$76.95Fright Hike: Chicago Halloween Bike Tour
Come get spooked on Bobby’s Fright Hike!
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$49.99Pizza City USA Pizza Coach Tour
Taste four different styles of pizzas in about three hours.
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$692019 Midwest Autumn Colors Excursion
To celebrate the glorious return of autumn, on October 26th and November 2nd we'll head out to superb Matthiessen State Park for an autumn colors hike!
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$36Naperville Food and Culture Walking Tour
Located just west of downtown Chicago, Naperville embodies Midwest friendliness and charm.
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$60Train and Walking Tour - Green Line: Prairie District
Get a sense for how Chicago's wealthiest residents lived around the turn of the century and what remains today.
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$70Downtown Architecture PLUS Graveyard Tour -- OCTOBER & NOVEMBER ONLY!
Though a few other tour companies in Chicago offer walking tours of downtown, none comes close to offering the degree of engagement, expertise, and passion that our tiny company does.
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$40Milwaukee Craft Breweries and Culinary Excursion
Chicago Weekend Explorers' day trip to Milwaukee shows you the best of Lake Michigan's northern jewel!
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$95Private Chicago Guide
This tour will allow you to have a private guide show you around the city for 4 hours.
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$275