Chicago Vacation Packages: Plan and Book Your Custom Vacation Today

You'll find everything you need to research, plan and book your custom Windy City vacation. You can explore the detailed articles, Calendar of Events, Points of Interest and more before making your reservations for a Chicago getaway on the shores of Lake Michigan!
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Chicago, IL Vacation Packages
A Taste of Chicago Vacation Getaway For a culinary and musical adventure in Chicago, book A Taste of Chicago Vacation Getaway, which includes three nights of lodging and the Chicago Odyssey Dinner Cruise.
Starting at
$342
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 120 hotels.
  • Chicago Odyssey Dinner Cruise
Chicago Attractions Vacation With the Chicago Attractions Vacation, you will have the opportunity to visit some of the greatest Chicago hotspots.
Starting at
$268
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 120 hotels.
  • CityPASS - Chicago, IL
Chicago Family Vacation Package For a great vacation full of family fun, book the Chicago Family Vacation Package, which includes four nights of lodging and CityPASS - Chicago.
Starting at
$311
per adult*

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Package Includes
  • CityPASS - Chicago, IL
  • 4 Nights' Lodging in your choice of over 120 hotels.
Chicago Fun Vacation Package If you like to have fun, you will absolutely adore the Chicago Fun Vacation Package, which includes four nights of lodging, the Chicago CityPASS, and the Prison Break escape room game!
Starting at
$363
per adult*

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Package Includes
  • 4 Nights' Lodging in your choice of over 120 hotels.
  • Prison Break
  • CityPASS - Chicago, IL
Chicago Museums Vacation Package If you would enjoy seeing the various museums in Chicago, book the Chicago Museums Vacation, which includes three nights of lodging and admission to the many exciting museums and more with a Chicago CityPASS!
Starting at
$268
per adult*

Book Now
Package Includes
  • 3 Nights' Lodging in your choice of over 120 hotels.
  • Chicago CityPASS
Chicago Romantic Getaway Package The Windy City is the perfect destination for you and your other half to let loose, and the planning is done for you with the Chicago Romantic Getaway Package.
Starting at
$265
per adult*

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Package Includes
  • Spirit of Chicago Dinner Cruise
  • 2 Nights' Lodging in your choice of over 120 hotels.
Chicago Shopping Excursion If you are looking for the ultimate shopping vacation, look no further than the Chicago Shopping Excursion which features two nights of lodging at Chicago area hotels as well as the Big Bus Chicago 1 Day Hop On/Hop Off Pass.
Starting at
$225
per adult*

Book Now
Package Includes
  • CityPASS - Chicago, IL
  • 2 Nights' Lodging in your choice of over 120 hotels.
Chicago Summer Vacation Enjoy an exciting summer vacation in Chicago with four nights of lodging as well as the CityPASS Chicago.
Starting at
$311
per adult*

Book Now
Package Includes
  • 4 Nights' Lodging in your choice of over 120 hotels.
  • CityPASS - Chicago, IL
Chicago's Six Flags Great America Getaway Enjoy a thrilling Chicago escapade with the Chicago CityPASS in this special vacation package along with two nights of lodging at your choice of hotels in the area.
Starting at
$225
per adult*

Book Now
Package Includes
  • Chicago CityPASS
  • 2 Nights' Accommodations in your choice of over 120 hotels.
Downtown Chicago Getaway For an incredible weekend escape to Chicago, book the Downtown Chicago Getaway, which includes two nights of lodging, and the CityPASS Chicago.
Starting at
$225
per adult*

Book Now
Package Includes
  • 2 Nights' Lodging in your choice of over 120 hotels.
  • CityPASS - Chicago, IL
Exciting Chicago Nightlife Package To experience the exciting nightlife that Chicago has to offer, book the Exciting Chicago Nightlife Package, which includes three nights of lodging and tickets to the Chicago Odyssey Dinner Cruise.
Starting at
$342
per adult*

Book Now
Package Includes
  • Chicago Odyssey Dinner Cruise
  • 3 Nights' Lodging in your choice of over 120 hotels.
Quick Chicago Weekend Getaway Get away from everyday life and into the spectacular nightlife and culture of Chicago with the Quick Chicago Weekend Getaway, which includes two nights of lodging at your choice of hotels in the area and tickets aboard the Chicago Architectural Sightseeing Cruise.
Starting at
$163
per adult*

Book Now
Package Includes
  • 2 Nights' Accommodations in your choice of over 120 hotels.
  • Chicago Architectural Sightseeing Cruise
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