Land Adventures in Chicago

About Chicago Land Adventures

At Expedia, we want you to get up close and personal with the city you're visiting, and our many types of land adventures provide you with the perfect opportunities to do so. While not every destination offers every single one of the following activities, these are just a few popular examples that are available in some cities.

Chicago Land Adventures Deals

A Slice of Chicago Pizza Tour
Food is a big deal in Chicago, from hot dogs to 3-star restaurants, but if there's one food Chicagoans rave about most, it's undoubtedly Chicago-style pizza. This gooey, cheesy, deep-dish pie with its thick, cornmeal crust was invented at Chicago’s... Read More
Bikes, Bites & Brews Bike Tour
Burn off calories _almost_ as fast as you consume them. Your bike ride around Chicago pauses all pedaling before the city's tastiest culinary treats. From a bubbling slice of deep-dish pizza and a mustard-slathered hot dog to frosted cupcakes and... Read More
City Lights at Night Bike Tour
A smooth, 8-mile ride along Chicago's famed urban landscapes is particularly enchanting come nightfall. With knowledgeable commentary, awe-inspiring landmarks, and incredible scenic views, this relaxing evening bike tour inspires, informs, and illuminates. Read More

Categories: Land Adventures, Tours & Sightseeing

3 hours

$45.50
per adult

Cupcake Walking Tour
There's simply no sweeter treat than the cupcake. Since the pint-sized-dessert trend swept Chicagoland, shops peddling these personal pastries have popped out of the oven by the baker's dozen. Sample your way through the best frostings and flavors in the... Read More
Explorer Pass: Choose up to 4 Museums, Attractions & Tours
Choose from more than 25 of Chicago's most amazing attractions, museums, and tours with this Explorer Pass and experience the city at your own pace. With your choice of up to 4 activities, enjoy access to famous locations as well... Read More
Favorite Food Walking Tour
The smells of the city's most famous foods entice you right from the beginning on this delicious culinary tour. Enjoy famous Chicago-style pizza, hot dogs, craft beers, and a brownie from the folks who invented it. Read More
Go Chicago Card
Discover Chicago’s finest museums, restaurants, cruises, and more with your Go Chicago Card. Combining some of the city’s top attractions, with advantages such as convenient discounts and skip-the-line access, this pocket-sized perk ensures you see all the Windy City has... Read More
Hop-On Hop-Off  City Tour by Chicago Trolley & Double Decker
From parks and piers to markets and museums—Chicago’s a cultural mixing pot of the old, the new, the cutting-edge, and the classically historic. This flexible hop-on hop-off tour frees you up to discover every sight and neighborhood that strikes your... Read More

$35.00
per adult

Italian Food Tour
Taste your way through Chicago's vibrant Magnificent Mile and Gold Coast on this Italian food-focused walking tour. Try mouthwatering Italian beef, homemade meatballs and marinara as well as savory rice balls. Read More
Lakefront Neighborhoods Bike Tour
Pedal out of Downtown Chicago and tour the quaint and locals-favorite neighborhoods that surround the city's core. This leisurely 7-mile (11-km) loop covers ground in upscale Gold Coast, historic Old Town, and North Side beaches, with your guide narrating each... Read More

Categories: Land Adventures, Tours & Sightseeing

3 hours

$45.50
per adult

Made in Chicago Designer Shopping Tour
Discover Chicago’s most exquisite designers, including Alice & Olivia, Kimberly Ovitz, and Wren, as you stroll through a unique and creative marketplace. Your personal shopping stylist shares success stories and local trivia while leading you to boutiques that only a... Read More

$50.00
per adult

Shop, Dine & Shuttle from Downtown or O'Hare International Aiport
Enjoy roundtrip shuttle service between downtown Chicago or O'Hare International Airport and Chicago's premier shopping outlet destinations—the Fashion Outlets of Chicago. Benefit from special discounts and rewards as you shop for deals at brand-name and high-end retailers and grab a... Read More
Shop, Explore, Play or Spa at The North Bridge Shops
The Shops at North Bridge span 6 blocks of Michigan Avenue, just steps from downtown Chicago's beautiful lakefront. Benefit from special discounts and rewards as you shop for deals at brand-name and high-end retailers in the heart of the Windy... Read More
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