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Top Chicago Unique Experiences

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9 results | All Chicago Tours

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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1170
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
240
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Underground Donut Tour: Chicago's First Donut Tour

Underground Donut Tour: Chicago's First Donut Tour

star-5
169
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
245
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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  • 3 hours
  • Taking safety measures
From
$193.20
From
$193.20
Taking safety measures

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
142
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$62.99
From
$62.99
Taking safety measures

Small-Group Chicago Food Tour: Gold Coast and Old Town

Small-Group Chicago Food Tour: Gold Coast and Old Town

star-5
160
Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.
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  • 3 hours
  • Free Cancellation
From
$74.67
From
$74.67

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
14
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$89.60
From
$89.60
Taking safety measures

Best of Chicago Tour Including a Deep-Dish Pizza

Best of Chicago Tour Including a Deep-Dish Pizza

star-2.5
5
Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$74.95
From
$74.95
Taking safety measures

Chicago Scavenger Hunt Adventure

Chicago Scavenger Hunt Adventure

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.
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  • 3 hours
  • Free Cancellation
From
$20.52
Price varies by group size
From
$20.52
Price varies by group size

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