Chicago Vacation Packages

Go Chicago Explorer Pass  - Chicago, IL Logo
Your Choice of Hotels
Save up to 32%
Package Starts at (USD):
$134.10
plus
tax
Per Adult
Medieval Times Dinner and Tournament Illinois - Schaumburg, IL Logo
LEGOLAND® Discovery Center Chicago - Schaumburg, IL Logo
Package Starts at (USD):
$90.18
plus
tax
Per Adult
Big Bus Tours Chicago - Chicago, IL Logo
Your Choice of Hotels
Save up to 38%
Package Starts at (USD):
$130.99
plus
tax
Per Adult
Go Chicago All-Inclusive Pass - Chicago, IL Logo
Your Choice of Hotels
Save up to 28%
Package Starts at (USD):
$173.30
plus
tax
Per Adult
LEGOLAND® Discovery Center Chicago - Schaumburg, IL Logo
Medieval Times Dinner and Tournament Illinois - Schaumburg, IL Logo
Your Choice of Hotels
Save up to 41%
Package Starts at (USD):
$141.96
plus
tax
Per Adult
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck - Chicago, IL Logo
Bikes, Bites, & Brews - Chicago's Signature Dishes - Chicago, IL Logo
Package Starts at (USD):
$423.39
plus
tax
Per Adult
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck - Chicago, IL Logo
Chicago's Ultimate City Bike Tour  - Chicago, IL Logo
Package Starts at (USD):
$389.09
plus
tax
Per Adult
Chicago Favorites Food and Walking Tour - Chicago, IL Logo
Your Choice of Hotels
Save up to 33%
Package Starts at (USD):
$130.17
plus
tax
Per Adult
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck - Chicago, IL Logo
Chicago Crime Tours - Chicago, IL Logo
Package Starts at (USD):
$382.20
plus
tax
Per Adult
Chicago's Chinatown Food and Walking Tour - Chicago, IL Logo
Big Bus Tours Chicago - Chicago, IL Logo
Save up to 10%
Package Starts at (USD):
$122.02
plus
tax
Per Adult
Medieval Times Dinner and Tournament Illinois - Schaumburg, IL Logo
Your Choice of Hotels
Save up to 47%
Package Starts at (USD):
$117.97
plus
tax
Per Adult
 Chicago's Lakefront Neighborhoods Bicycle Tour - Chicago, IL Logo
Your Choice of Hotels
Save up to 36%
Package Starts at (USD):
$105.67
plus
tax
Per Adult
Big Bus Tours Chicago - Chicago, IL Logo
LEGOLAND® Discovery Center Chicago - Schaumburg, IL Logo
Save up to 9%
Package Starts at (USD):
$72.52
plus
tax
Per Adult
Go Chicago All-Inclusive Pass - Chicago, IL Logo
Medieval Times Dinner and Tournament Illinois - Schaumburg, IL Logo
Package Starts at (USD):
$187.71
plus
tax
Per Adult
Go Chicago All-Inclusive Pass - Chicago, IL Logo
Chicago Crime Tours - Chicago, IL Logo
Package Starts at (USD):
$168.52
plus
tax
Per Adult
360 CHICAGO - Chicago, IL Logo
Your Choice of Hotels
Save up to 40%
Package Starts at (USD):
$85.78
plus
tax
Per Adult
360 CHICAGO - Chicago, IL Logo
Chicago Favorites Food and Walking Tour - Chicago, IL Logo
Package Starts at (USD):
$112.39
plus
tax
Per Adult
Big Bus Tours Chicago - Chicago, IL Logo
360 CHICAGO - Chicago, IL Logo
Save up to 8%
Package Starts at (USD):
$82.53
plus
tax
Per Adult

Want to soak in all the sights of the Windy City? A Chicago vacation package is perfect for you! This city-home of deep-dish pizza, impressive skyscrapers, and legendary blues music offers a delightful melting pot of Chicago vacation experiences waiting to be discovered.

Picture yourself strolling down a bustling hub of high-end shopping avenues, towering architectural wonders, and notable landmarks. Each vacation package is usually designed to ensure you get the best view of the iconic destination.

From luxurious Chicago hotels to vibrant local neighborhoods, you'll be immersed in a palette of diverse experiences. Enjoy a leisurely walk along the lakefront, scented with breezes from the water and the elements of urban life merging. Or get lost in the colorful, cultural tapestry of neighborhoods, each with unique character and charm.


  • Chicago's food scene is a gastronomic adventure all in its own. No two meals are alike here, with everything from world-famous deep-dish pizza to upscale dining experiences.

  • The city's arts scene is another facet that's not to be overlooked. With numerous museums, galleries, theatres, and music venues, your cultural cravings are guaranteed to be satisfied.

  • And let's not forget about the city's love for sports. With teams in nearly every major sports league, there's always a game to catch around town.


In a nutshell,  Chicago vacation packages would take you through an all-encompassing experience that combines the best of city life, scenic beauty, cultural richness, and culinary delights. It's your route to a kaleidoscope of experiences that the city has to offer. The vacation packages to Chicago, with its unlimited adventures, is a vacation that you'd want to revisit time and time.

Unearth the Magic of the Windy City: Book Your Chicago Vacation with Tripster Today!


Embark on the adventure of a lifetime with Tripster's unforgettable vacation packages from Chicago. Experience the enchanting allure of the Windy City, steeped in rich history, diverse culture, and irresistible cuisine. From the awe-striking skyscrapers to the serene beauty of Lake Michigan, every moment brims with possibilities. Allow Tripster to be your trusted guide, ensuring top-notch accommodations, crowd-pleasing itineraries, and insightful local recommendations. With tailor-made packages for every budget and preference, your dream Chicago vacation is just a click away. Book your Chicago vacation with Tripster today and start creating memories that will last a lifetime!