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Chicago, Illinois Vacation Packages, Tours, Lodging, Dining & Attraction Tickets

Book your Windy City getaway online with easy lodging, attraction, and dining reservations! There's plenty to see and do in this sprawling metropolis, including exploring Wrigley Field, the Sears Tower, and other landmarks, enjoying a dinner and show at Medieval Times Chicago, or experiencing big thrills at Six Flags Great America.
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Chicago, IL Vacation Packages
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 Heist Escape Game, as well as the Chicago Architectural Sightseeing Cruise!
Starting at
$198
per adult*

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Package Includes
  • Chicago Architectural Sightseeing Cruise
  • The Heist Escape Game
  • 3 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 and the Prison Break escape room game!
Starting at
$240
per adult*

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Package Includes
  • 4 Nights' Lodging in your choice of over 120 hotels.
  • Prison Break
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
$339
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 120 hotels.
  • Chicago Odyssey Dinner Cruise
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