Land Adventures in Chicago

Chicago Land Adventures

Once you’ve dried off from your swim in Lake Michigan (or bundled up to explore the Windy City in the winter), loads of land adventures await you in Chicago. Experience the bounty of activities in Millennium Park or go on a walking tour replete with snacks and brew. No matter your travel style, you can always find tickets and passes for the Chicago activities that fit your interests. Best of all, thanks great deals here on Expedia, you never have to break your budget to explore the city to the fullest.

Chicago Land Adventures Deals

Amazing Scavenger Hunt Adventure
Embark on an interactive tour of Chicago and discover the city while using hints and completing unique challenges. See landmarks and historical locations as you solve clues on your smartphone that lead you on a memorable tour of the Windy... Read More

Categories: Adventures, Land Adventures, Tours & Sightseeing

3 hours

Free cancellation

$38
per Group

Architectural Masterpieces of the Loop Walking Tour
Chicago is home to some of America's most noteworthy architectural achievements, including the country's very first skyscraper. Take a fascinating journey back into history and learn all about the progression of architecture over the course of the city's history in... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Architectural Walking Tour of Chicago's River Walk
Avoid having a "been-there, done-that" experience in Chicago during a tour that shows you a hidden side of the Windy City. Explore the city's world-renowned architecture and learn about details of some of its buildings that are too often overlooked... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Art Deco Skyscrapers: Riverfront Trolley & Walking Tour
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

$25
per Traveler

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

$79
per Adult

Bucktown & Wicker Park Beer Tasting & Bar Tour
Get off the beaten track and into some of Chicago's most welcoming and history-filled bars during a beer-tasting tour that covers the Bucktown and Wicker Park districts. Visit drinking establishments that are teeming with character while learning fascinating tidbits about... Read More
Chocolate Lover's Walking Tour
Satisfy your sweet tooth on this mouthwatering walking tour of the Magnificent Mile, stopping at several artisan chocolate boutiques for samples of their finest produce. Walk with an expert guide who leads you on a tasty tour of some of... Read More

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

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Coffee Walking Tour
Given the city's famously chilly and windy weather, it's no wonder that Chicagoans love to cozy up with a hot cup of coffee. Delve into Chicago’s café scene with a tour of its best coffee shops, sipping java and nibbling... Read More

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

2 hours

Free cancellation

Save!

$25

$22
per Traveler

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!

$25

$22
per Traveler

Daily Bike Rental
Chicago is recognized as one of the most bike-friendly cities in the United States by cycling enthusiasts, and for good reason. Get set up with a comfortable bike and a detailed map of the city's numerous bike lanes and trails,... Read More

Categories: Land Adventures, Tours & Sightseeing

12 hours

Free cancellation

$41
per Adult

Downtown & Skyline Vistas Trolley Tour
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

$25
per Traveler

Evolution of the Skyscraper Walking Tour
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 façades, explore the Windy City’s building background from the ground up.... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour 30 minutes

$20
per Traveler

Explorer Pass: Choose 3 or 5 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

$72
per Adult

Exploring Old & New Architecture Walking Tour
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
per Traveler

Favorite Food & Drink 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, Italian beef, craft beers, and a brownie from the folks who invented it. Read More

$55
per Adult

Gangster History Walking Tour
Explore the history of Chicago's underworld on this guided walking tour to some of the city's most infamous mob and gang-related spots. Learn about the outlaw days of the Second City, from Mad Sam Destefano to Al Capone, and see... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$18

$15
per Traveler

Historic Chicago Walking Bar Tour
Sip drinks and nibble on appetizers at 3 historic bars as you learn about the city's entertainment and party history while marveling at incredible architecture. Stroll at a leisurely pace with your guide to appreciate the iconic architecture and pubs... 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
per Traveler

Hop-On Hop-Off Bus Tour
Tour the sights of Chiacgo—renowned for its blues, jazz, comedy, shopping, and dining—at your own pace on a double-decker bus. This hop-on hop-off tour takes you all around the city’s major landmarks including Grant's Park, the Magnificent Mile, 360 Chicago,... Read More

Categories: Land Adventures, Tours & Sightseeing

1 day

Free cancellation

$35
per Adult

Hop-On Hop-Off City Tour
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

$33
per Adult

Italian Food Walking 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!

$25

$22
per Traveler

Lake View & Lincoln Park Beer Tasting & Bar Tour
Chicago's Lake View and Lincoln Park districts are home to a treasure trove of welcoming, locally owned bars and breweries. Join a group of like-minded beer lovers and visit the many drinking establishments that pepper these neighborhoods. 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

Free cancellation

$48
per Adult

Loop & South Loop Beer Tasting & Bar Tour
Delve into Chicago's colorful past during a tour that takes you to some of the Loop and South Loop's most history-filled drinking establishments. This beer-tasting experience opens your eyes to the role that alcohol played in the enterprises of the... Read More
Loop Interior Architecture & Pedway Walking Tour
Strolling at a leisurely pace, follow your guide on a route weaving through buildings and secret shortcuts. Step inside landmark buildings like Marshall Field's Department Store and the Chicago Cultural Center to appreciate magnificent lobbies, corridors, and the underground Pedway... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$26
per Traveler

Macy's Star Shopper Package
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
per Traveler

Millennium Park Walking Tour
Discover the fascinating history of Millennium Park on this quick tour around its unique grounds, where spectacular sculptures and art installations cover this iconic Chicago spot. Stand before the mirrored bean known as Cloud Gate, and snap photos of the... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour

$15
per Traveler

Millennium Park: Beyond the Bean Walking Tour
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
per Traveler

Mobsters of the South Side Bike Tour
Pedal your way into Chicago’s seedy, crime-riddled past with a historical biking tour that takes you into what was once the city’s mob-run underbelly. Learn about Al Capone and the Chicago Outfit, learning about Chi-town’s dark side on this 13-mile... Read More

Categories: Land Adventures, Tours & Sightseeing

4 hours

Free cancellation

$60
per Adult

Modern Skyscrapers Walking Tour
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
per Traveler

Open Your Eyes: Secrets of the Loop
Discover some of the hidden secrets of Chicago's bustling Loop, including hidden details and untold stories that add bits of color and texture to the city's overall narrative. Stroll through the streets with a guide and learn about the often-overlooked... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Pizza Walking Tour
Satiate your appetite with warm and savory deep-dish pizza as you pop into 4 of the best pizzerias in town. Follow your guide and see iconic places where movies were filmed in the Windy City as you gain knowledge about... Read More

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

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Riverwalk Food Tour
Get to know the culinary offerings of the Chicago Riverwalk with a tour that introduces you to the great tastes of the Windy City. See the breathtaking architecture along the Chicago River and some of the best views this city... Read More

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

2 hours

Free cancellation

Save!

$25

$22
per Traveler

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

Categories: Attractions, Land Adventures, Tours & Sightseeing

1 day

Free cancellation

$46
per Traveler

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
per Traveler

Walking Tour of River North & Cathedral District
Learn all about Chicago's rebirth as the "Second City" after the infamous Great Fire of 1871 during this fascinating guided tour. A friendly guide takes you on a trip through time and explains the amazing story of tragedy and resilience... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Walking Tour of the Dazzling Interiors of the Loop
Experience the energetic buzz of activity that thrives in the Loop, Chicago's commercial core. Join a guide and see some of this district's most dazzling buildings and interiors, where businesspeople and politicians rush from meeting to meeting and tourists scurry... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Walking Tour of The West Loop & Wolf Point
All of Chicago's neighborhoods are rich with culture, but the West Loop is perhaps the closest and most accessible off-the-beaten-path experience for getting to know this world-famous city while sticking close to downtown. Explore this district and marvel at epic... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Back to top