Chicago Vacation Packages: Plan and Book Your Custom Vacation Today

Custom Vacation Package 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 an Chicago getaway on the shores of Lake Michigan!
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Chicago, IL Vacation Packages
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, admission to Six Flags Great America, a 3 Day Go Chicago Card and the Medieval Times Dinner & Tournament!
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Package Includes
  • 4 Nights' Lodging in your choice of over 154 hotels.
  • Six Flags Great America
  • Medieval Times Dinner & Tournament
  • 3 Day Go Chicago Card
Chicago Fun Vacation Package Book Now
If you like to have fun, you will absolutely adore the Chicago Fun Vacation Package, which includes four nights of lodging, admission to Six Flags Great America, a 3 Day Go Chicago Card and the Medieval Times Dinner & Tournament!
Package Includes
  • 4 Nights' Lodging in your choice of over 154 hotels.
  • Six Flags Great America
  • Medieval Times Dinner & Tournament
  • 3 Day Go Chicago Card
Chicago Attractions Vacation With the Chicago Attractions Vacation, you will have the opportunity to see more than 25 attractions with a 3-day Go Chicago Card and three nights of lodging!
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Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • 3-day Go Chicago Card
Chicago Attractions Vacation Book Now
With the Chicago Attractions Vacation, you will have the opportunity to see more than 25 attractions with a 3-day Go Chicago Card and three nights of lodging!
Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • 3-day Go Chicago Card
Chicago Family Vacation Package For a great vacation full of family fun, book the Chicago Family Vacation Package, which includes four nights of lodging, Medieval Times Dinner & Tournament, and access to 25 exciting attractions with a 3-day Go Chicago Card!
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Package Includes
  • 4 Nights' Lodging in your choice of over 154 hotels.
  • Medieval Times Dinner & Tournament
  • 3-day Go Chicago Card
Chicago Family Vacation Package Book Now
For a great vacation full of family fun, book the Chicago Family Vacation Package, which includes four nights of lodging, Medieval Times Dinner & Tournament, and access to 25 exciting attractions with a 3-day Go Chicago Card!
Package Includes
  • 4 Nights' Lodging in your choice of over 154 hotels.
  • Medieval Times Dinner & Tournament
  • 3-day Go Chicago Card
Chicago's Six Flags Great America Getaway Enjoy a thrilling Chicago escapade with Chicago's Six Flags Great America Getaway - included in this special vacation package is two night's at the Chicago lodging and tickets to Six Flags Great America & the accompanying Hurricane Harbor Water Park.
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Package Includes
  • 2 Nights' Accommodations in your choice of over 154 hotels.
  • Six Flags Great America
Chicago's Six Flags Great America Getaway Book Now
Enjoy a thrilling Chicago escapade with Chicago's Six Flags Great America Getaway - included in this special vacation package is two night's at the Chicago lodging and tickets to Six Flags Great America & the accompanying Hurricane Harbor Water Park.
Package Includes
  • 2 Nights' Accommodations in your choice of over 154 hotels.
  • Six Flags Great America
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 the Chicago Grand Tour and two night's lodging.
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Package Includes
  • 2 Nights' Accommodations in your choice of over 154 hotels.
  • Inside Chicago Grand Tour (Tour #3)
Quick Chicago Weekend Getaway Book Now
Get away from everyday life and into the spectacular nightlife and culture of Chicago with the Quick Chicago Weekend Getaway, which includes the Chicago Grand Tour and two night's lodging.
Package Includes
  • 2 Nights' Accommodations in your choice of over 154 hotels.
  • Inside Chicago Grand Tour (Tour #3)
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, the Bikes, Bites, and Brews Bicycle Tour, and the Medieval Times Dinner & Tournament in Schaumburg, IL!
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Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • Medieval Times Dinner & Tournament - Schaumburg, IL
  • Chicago Culinary Bike Tour
A Taste of Chicago Vacation Getaway Book Now
For a culinary and musical adventure in Chicago, book A Taste of Chicago Vacation Getaway, which includes three nights of lodging, the Bikes, Bites, and Brews Bicycle Tour, and the Medieval Times Dinner & Tournament in Schaumburg, IL!
Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • Medieval Times Dinner & Tournament - Schaumburg, IL
  • Chicago Culinary Bike Tour
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!
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Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • Chicago CityPASS
Chicago Museums Vacation Package Book Now
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!
Package Includes
  • 3 Nights' Lodging in your choice of over 154 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.
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Package Includes
  • 2 Nights' Lodging in your choice of over 154 hotels.
  • Go Chicago Card - Chicago, IL
Chicago Romantic Getaway Package Book Now
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.
Package Includes
  • 2 Nights' Lodging in your choice of over 154 hotels.
  • Go Chicago Card - Chicago, IL
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.
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Package Includes
  • 2 Nights' Lodging in your choice of over 154 hotels.
Chicago Shopping Excursion Book Now
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.
Package Includes
  • 2 Nights' Lodging in your choice of over 154 hotels.
Chicago Summer Vacation Enjoy an exciting summer vacation in Chicago with four nights of lodging, a Chicago CityPass and admission to Six Flags Great America!
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Package Includes
  • 4 Nights' Lodging in your choice of over 154 hotels.
  • Chicago CityPass
  • Six Flags Great America
Chicago Summer Vacation Book Now
Enjoy an exciting summer vacation in Chicago with four nights of lodging, a Chicago CityPass and admission to Six Flags Great America!
Package Includes
  • 4 Nights' Lodging in your choice of over 154 hotels.
  • Chicago CityPass
  • Six Flags Great America
Chicago's Medieval Times Dinner Tournament Package Gather 'round, m'lords & ladies, for the Medieval Times Dinner Tournament Package in Chicago, which includes tickets to the hottest dinner theater show around and two nights lodging in one of Chicago's grand hotels, condos or resorts.
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Package Includes
  • 2 Nights' Accommodations in your choice of over 154 hotels.
  • Medieval Times Dinner & Tournament
Chicago's Medieval Times Dinner Tournament Package Book Now
Gather 'round, m'lords & ladies, for the Medieval Times Dinner Tournament Package in Chicago, which includes tickets to the hottest dinner theater show around and two nights lodging in one of Chicago's grand hotels, condos or resorts.
Package Includes
  • 2 Nights' Accommodations in your choice of over 154 hotels.
  • Medieval Times Dinner & Tournament
Downtown Chicago Getaway For an incredible weekend escape to Chicago, book the Downtown Chicago Getaway, which includes two nights of lodging, and the Chicago Lakefront Bicycle Tour.
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Package Includes
  • 2 Nights' Lodging in your choice of over 154 hotels.
  • Chicago Lakefront Bicycle Tour - 3 Hour Tour Through Lakefront Historic & Famous Residences
Downtown Chicago Getaway Book Now
For an incredible weekend escape to Chicago, book the Downtown Chicago Getaway, which includes two nights of lodging, and the Chicago Lakefront Bicycle Tour.
Package Includes
  • 2 Nights' Lodging in your choice of over 154 hotels.
  • Chicago Lakefront Bicycle Tour - 3 Hour Tour Through Lakefront Historic & Famous Residences
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 admission to the Chicago Dinner Cruise.
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Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • Chicago Dinner Cruise
Exciting Chicago Nightlife Package Book Now
To experience the exciting nightlife that Chicago has to offer, book the Exciting Chicago Nightlife Package, which includes three nights of lodging and admission to the Chicago Dinner Cruise.
Package Includes
  • 3 Nights' Lodging in your choice of over 154 hotels.
  • Chicago Dinner Cruise
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