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
$309
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 117 hotels.
  • Chicago Odyssey Dinner Cruise
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 the Chicago Explorer Pass 3 Choice pass.
Starting at
$192
per adult*

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Package Includes
  • 2 Nights' Accommodations in your choice of over 117 hotels.
  • Chicago Explorer Pass 3 Choice
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 the Chicago Architectural Sightseeing Cruise.
Starting at
$254
per adult*

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Package Includes
  • Chicago Architectural Sightseeing Cruise
  • 4 Nights' Lodging in your choice of over 117 hotels.
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
$188
per adult*

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Package Includes
  • 2 Nights' Lodging in your choice of over 117 hotels.
  • Spirit of Chicago Lunch Cruise with Buffet
Chicago Attractions Vacation With the Chicago Attractions Vacation, you will have the opportunity to visit some of the greatest Chicago hotspots.
Starting at
$191
per adult*

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Package Includes
  • 3 Nights' Lodging in your choice of over 117 hotels.
  • Chicago City Hop-on Hop-off Tour: One Day Pass
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 Outbreak Escape Room game!
Starting at
$235
per adult*

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Package Includes
  • 4 Nights' Lodging in your choice of over 117 hotels.
  • Outbreak Escape Room
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 Adler Planetarium and Astronomy Museum and the Art Institute of Chicago Fast Pass Admission.
Starting at
$229
per adult*

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Package Includes
  • Adler Planetarium and Astronomy Museum
  • Art Institute of Chicago Fast Pass Admission
  • 3 Nights' Lodging in your choice of over 117 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 Chicago Girls Getaway Luxury Shopping Experience.
Starting at
$1,383
per adult*

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Package Includes
  • Chicago Girls Getaway Luxury Shopping Experience
  • 2 Nights' Lodging in your choice of over 117 hotels.
Chicago Summer Vacation Enjoy an exciting summer vacation in Chicago with four nights of lodging as well as the Chicago Odyssey Lunch Cruise.
Starting at
$206
per adult*

Book Now
Package Includes
  • 4 Nights' Lodging in your choice of over 117 hotels.
  • Chicago Odyssey Lunch Cruise
Chicago's Six Flags Great America Getaway Enjoy a thrilling Chicago escapade with two nights of lodging at your choice of hotels in the area.
Starting at
$113
per adult*

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Package Includes
  • 2 Nights' Accommodations in your choice of over 117 hotels.
Downtown Chicago Getaway For an incredible weekend escape to Chicago, book the Downtown Chicago Getaway, which includes two nights of lodging, and the Chicago Architectural Sightseeing Cruise.
Starting at
$159
per adult*

Book Now
Package Includes
  • Chicago Architectural Sightseeing Cruise
  • 2 Nights' Lodging in your choice of over 117 hotels.
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
$309
per adult*

Book Now
Package Includes
  • Chicago Odyssey Dinner Cruise
  • 3 Nights' Lodging in your choice of over 117 hotels.
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