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

90-Minute Express Segway Tour
Glide your way through the Windy City on this 2-wheeled adventure. Ride past signature landmarks, through beautiful parks, and along the magnificent shoreline of Lake Michigan. This guided express Segway tour is the perfect way to see a lot of... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour 30 minutes

Free cancellation

$50
per adult

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

$50
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

$30
per adult

Bike & Brew Tour
Enjoy a scenic bike ride along Chicago's famous Lakefront Trail as you journey to unique breweries for beer and food samples. Visit Chinatown and Pilsen neighborhoods where the brew culture is particularly strong. Your guide tells you all about the... Read More

$40
per adult

Bike & Yoga Tour on Chicago's Lakefront Trail
Bike Chicago's tranquil, scenic Lakefront Trail in the quiet of the morning—a fantastic way to get to know the city and its people. Stop at one of the many sandy beaches along the way and meet up with a Vinyasa... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$70
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

$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!

$50

$25
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

$48
per adult

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!

$50

$25
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

$25
per adult

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

$45
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

$30
per adult

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

$15
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
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 adult

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, hot dogs, craft beers, and a brownie from the folks who invented it. Read More

$55
per adult

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

$34
per adult

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 adult

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

$39
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!

$50

$25
per adult

Kid-Friendly Bike Tour
Perfect for families with kids of all ages, this easy cruise through Chicago’s parks and along its lakefront trails is specially designed for tikes under 10. Cover 4. 5 miles (7 km) at an easy pace as you pedal to... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

Free cancellation

$42
per adult

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

Lakefront Segway Tour
Experience Chicago's sights aboard a Segway on a guided excursion. Cruise through the Windy City, past iconic landmarks, gorgeous parks, and magnificent Lake Michigan. In just a few hours, see all of the top sights while listening to entertaining commentary.... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$75
per adult

Lincoln Park Adventure
Park your car and grab a bike to experience Chicago at your own pace. As one of the most popular bike tours, this adventure around Lincoln Park takes you down lake-front trails free of any traffic. Enjoy a serene 2-wheel... Read More

Categories: Land Adventures, Tours & Sightseeing

3 hours

Free cancellation

$40
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 adult

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 adult

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 adult

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 adult

Museums & Parks Sunset Bike Tour
Ride along the lakefront visiting parks and gardens as the refreshing lake breeze races across your face and the sound of waves smashing across the shoreline envelops you. Whether Chicago is your home town or this is your first time... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

Free cancellation

$42
per adult

Night City Bike Tour with Fireworks
Spend an enchanting evening biking to Chicago's main attractions as they're illuminated by the twinkling lights of the city. See The Bean sculpture at Millennium Park and the Crown Fountain's intriguing video art display. Top it all off with spectacular... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$40
per adult

Noble Square & Wicker Park Walking Tour with Food
The architecture, food, and people of 2 vibrant and fast-changing neighborhoods make for a great look at the state of Chicago today. See how Wicker Park has transformed from one of the city's roughest neighborhoods to one of its coolest,... Read More

$45
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!

$50

$25
per adult

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!

$50

$25
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
per adult

Skyscraper Segway Tour
Chicago's iconic skyline is marked by some of the tallest and most architecturally impressive skyscrapers in the country. Step aboard an easy-to-operate Segway and cruise along the city's streets during a tour that lets you marvel at these magnificent buildings... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$75
per adult

Small-Group Little Arabia Food Tour
Fresh bread slathered with olive oil-splashed vegetable spreads, grilled meats scattered wiith fragrant herbs and jewel-like pomegranate seeds, and desserts perfumed with rosewater and honey—the fresh and luxurious flavors of Middle Eastern cuisine are at your fingertips on this delicious... Read More

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

3 hours 30 minutes

Free cancellation

$90
per adult

Small-Group Little India Food Tour
Savor the flavors of the subcontinent right in the heart of the Windy City on this delicious, food-focused walking tour in Chicago's Little India neighborhood. Sample dishes from India, Pakistan, and Bangladesh, browse specialty shops, and even get a traditional... Read More

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

3 hours 30 minutes

Free cancellation

$90
per adult

Smartphone-Guided City Scavenger Hunt
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 adult

Sweets & Spirits Dessert Tour
Indulge your sweet tooth and your thirst as you sample the best desserts and cocktails in Chicago. Gorge on samples of chocolates and baked goods before washing it down with creative cocktails. The city is your playground as you partake... Read More

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

2 hours 30 minutes

Free cancellation

$55
per adult

The Ultimate Architecture Tour
Art Deco icons, industrial-era giants, and ultra-modern, glass-and-steel skyscrapers—Chi-town's packed with impressive edifices, and each one has a story to tell. Hear the tall tales behind Chicago's architectural gems on this intriguing look at the Windy City's must-see structures. Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour 30 minutes

Free cancellation

$22
per adult

Back to top