Top Chicago Half-day Tours

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some...
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Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle...
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Taste all of Chicago’s classic eats on this four-hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike...
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Expect the exceptional on this 3-hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and...
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Discover fine dining, upscale entertainment and unparalleled riverfront views aboard the brand new Odyssey Chicago River! The Odyssey Chicago River is a brand new, glass enclosed...
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What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a...
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Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that...
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Take a detour off the beaten path, and explore the flavors of Chicago’s vibrant West Side with Bobbys's Bike Hike, America's longest running city bike...
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Let us put the Custom in Chicago Custom tours… What are your must-see venues? What would personalize your excursion? We’ll plan your tour and make...
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On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor...
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Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, America’s longest running city bicycle tour...
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Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle...
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Join this 3-hour tour of Chicago's food scene, and see what sets this friendly mid-western metropolis apart. On this 12 person maximum walking tour of...
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This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...
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There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is...
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This Tour is the quickest, best way to explore a place that you are visiting for the first time, we take you to all the...
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This could very well be the best food tour on the planet. Why? Nothing beats the freedom of a bicycle to explore so many unique...
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Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern...
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Go for a scenic stroll through Chicago’s urban neighborhoods on this private tour accompanied by a friendly guide. Admire the oldest skyscraper and learn everything...
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Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun...
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There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3-hour guided walking and food tour through the Chicago Loop,...
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