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.

Hiking and Walking Tours

Lace up your hiking boots and hit the trails, be they dirt paths or city sidewalks. Climb up a mountain for a view of the landscape, venture around a lake, or take a guided walking tour of the city. Hiking is one way to get your heart rate up while you get in touch with the world around you.

Biking

Rent a bicycle to explore the city on wheels. Bike riding lets you see the town on your own terms, whether you’re visiting the city’s landmarks or admiring the attractions. Work up an appetite and then stop at a local coffee shop or restaurant to round out the day. Some locations even rent e-bikes to amp up the fun!

ATV Tours

Create your own path when you hit the trails on an all-terrain vehicle. These tours let you steer your way around and explore the city from a different perspective. Go off-roading or forge your way on the designated ATV paths.

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

$45.00
per adult

Art Deco Skyscrapers: Riverfront Trolley & Walking Tour by the Chicago Architecture Foundation
Crane your neck and gaze at the looming Art Deco edifices that dot the streets of downtown Chicago. This classic architectural style is emblematic of the Windy City, and your tour takes you to 3 of its most shining examples... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$30.00
per adult

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

$72.00
per adult

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

Free cancellation

$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

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$50.00

$25.00
per adult

Downtown & Skyline Vistas Trolley Tour by the Chicago Architecture Foundation
Climb aboard a charming trolley and dive into the dynamic parks, scenic drives, and vital waterways of the Windy City. Hear about the intriguing development of this Midwestern metropolis and enjoy various stops that offer unique perspectives and dramatic views... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$30.00
per adult

Evolution of the Skyscraper Walking Tour by the Chicago Architecture Foundaiton
Start with simple stones and end with high-strength steel as you embark on an architectural adventure to track the development of Chicago's iconic skyscrapers. From stately columns to ostentatious facades, explore the Windy City's building background from the ground up.... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour

$15.00
per adult

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

$92.00
per adult

Exploring Old & New Architecture Walking Tour by the Chicago Architecture Foundation
Uncover the dynamic architectural scenes unfolding amid the bustling streets and intersections of downtown Chicago. See elegant stonework displayed next to modern high-rises and find out how the city's architects approached the development of the Windy City's urban landscape. Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20.00
per adult

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

$54.45
per adult

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
Historic Treasures of Culture & Commerce Architecture Walking Tour
Uncover the Windy City's exceptional architecture as you stroll between historic department stores, luxurious hotels, and towering office buildings. With a volunteer from the Chicago Architecture Foundation leading the way, explore the work of Chicago's ambitious architects on this walking... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20.00
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

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$50.00

$25.00
per adult

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

Free cancellation

$45.50
per adult

Macy's Star Shopper Package by Shop America
Browse Macy's modern fashion while you walk through this historic department store. Formerly a Marshall Field's, the building is known for providing an extravagant and innovative shopping experience. Read More

Categories: Attractions, Land Adventures, Tours & Sightseeing

3 days

Free cancellation

$42.00
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

Millennium Park: Beyond the Bean Walking Tour by the Chicago Architecture Foundation
Stroll the grounds of Millennium Park to discover marvelous sculptures, sprawling gardens, and wide-open fields beneath geometric trellises. Originally designed to commemorate the new millennium, and highly criticized at the time, this park has become the crown jewel of Chicago's... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20.00
per adult

Modern Skyscrapers Walking Tour by the Chicago Architecture Foundation
Examine the rise of Chicago's skyline as you wander between stunning modernist structures and elegant minimalist skyscrapers on this fascinating architectural tour. With a volunteer from the Chicago Architecture Foundation leading the way, uncover the newest buildings in the Windy... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20.00
per adult

Museums & Parks Sunset Bike Tour
Your bicycle tour begins with a journey through the local neighborhoods of Gold Coast, Lincoln Park, and Wrigleyville. Ride along the lakefront visiting parks and gardens as the refreshing lake breeze races across your face and the sound of waves... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

Free cancellation

$37.00
per adult

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

$40.00
per adult

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