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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 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
$175
per adult*

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Package Includes
  • 2 Nights' Lodging in your choice of over 115 hotels.
  • Spirit of Chicago Lunch Cruise with Buffet
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
$291
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 115 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
$141
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 115 hotels.
  • Chicago City Hop-on Hop-off Tour: One Day Pass
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