Research, Plan & Book Your Custom Chicago, Illinois Vacation Package with Lodging, Activities and Special Events
 

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
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 137 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 137 hotels.
  • Medieval Times Dinner & Tournament - Schaumburg, IL
  • Chicago Culinary Bike Tour
Chicago Attractions Vacation With the Chicago Attractions Vacation, you will have the opportunity to visit one of the nation's most popular theme parks with the Six Flags Great America, Six Flags Hurricane Harbor and three nights of lodging!
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Package Includes
  • 3 Nights' Lodging in your choice of over 137 hotels.
  • Six Flags Great America
  • Six Flags Hurricane Harbor
Chicago Attractions Vacation Book Now
With the Chicago Attractions Vacation, you will have the opportunity to visit one of the nation's most popular theme parks with the Six Flags Great America, Six Flags Hurricane Harbor and three nights of lodging!
Package Includes
  • 3 Nights' Lodging in your choice of over 137 hotels.
  • Six Flags Great America
  • Six Flags Hurricane Harbor
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 137 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 137 hotels.
  • Medieval Times Dinner & Tournament
  • 3-day Go Chicago Card
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 Big Bus Chicago 3 Day Hop On/Hop Off Pass and the Medieval Times Dinner & Tournament!
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Package Includes
  • 4 Nights' Lodging in your choice of over 137 hotels.
  • Big Bus Chicago 3 Day Hop On Hop Off Pass
  • Medieval Times Dinner & Tournament
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, the Big Bus Chicago 3 Day Hop On/Hop Off Pass and the Medieval Times Dinner & Tournament!
Package Includes
  • 4 Nights' Lodging in your choice of over 137 hotels.
  • Big Bus Chicago 3 Day Hop On Hop Off Pass
  • Medieval Times Dinner & Tournament
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 137 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 137 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 137 hotels.
  • Grand Tour of Chicago and Hancock Tower
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 137 hotels.
  • Grand Tour of Chicago and Hancock Tower
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.
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Package Includes
  • Big Bus Chicago 1 Day Hop On Hop Off Pass
  • 2 Nights' Lodging in your choice of over 137 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 as well as the Big Bus Chicago 1 Day Hop On/Hop Off Pass.
Package Includes
  • Big Bus Chicago 1 Day Hop On Hop Off Pass
  • 2 Nights' Lodging in your choice of over 137 hotels.
Chicago Summer Vacation Enjoy an exciting summer vacation in Chicago with four nights of lodging, the Chicago Extreme Thrill Ride Cruise, and the Chicago Grand Tour & Chicago Style Pizza.
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Package Includes
  • 4 Nights' Lodging in your choice of over 137 hotels.
  • Chicago Extreme Thrill Ride Cruise
  • Chicago Grand Tour & Chicago Style Pizza
Chicago Summer Vacation Book Now
Enjoy an exciting summer vacation in Chicago with four nights of lodging, the Chicago Extreme Thrill Ride Cruise, and the Chicago Grand Tour & Chicago Style Pizza.
Package Includes
  • 4 Nights' Lodging in your choice of over 137 hotels.
  • Chicago Extreme Thrill Ride Cruise
  • Chicago Grand Tour & Chicago Style Pizza
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 137 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 137 hotels.
  • Medieval Times Dinner & Tournament
Chicago's Six Flags Great America Getaway Enjoy a thrilling Chicago escapade with the Six Flags Great America included in this special vacation package along with two nights of lodging at your choice of hotels in the area.
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Package Includes
  • Six Flags Great America
  • 2 Nights' Accommodations in your choice of over 137 hotels.
Chicago's Six Flags Great America Getaway Book Now
Enjoy a thrilling Chicago escapade with the Six Flags Great America included in this special vacation package along with two nights of lodging at your choice of hotels in the area.
Package Includes
  • Six Flags Great America
  • 2 Nights' Accommodations in your choice of over 137 hotels.
Downtown Chicago Getaway For an incredible weekend escape to Chicago, book the Downtown Chicago Getaway, which includes two nights of lodging, and the 1 Day Go Chicago Card.
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Package Includes
  • 2 Nights' Lodging in your choice of over 137 hotels.
  • 1 Day Go Chicago Card
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 1 Day Go Chicago Card.
Package Includes
  • 2 Nights' Lodging in your choice of over 137 hotels.
  • 1 Day Go Chicago Card
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
  • Chicago Dinner Cruise
  • 3 Nights' Lodging in your choice of over 137 hotels.
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
  • Chicago Dinner Cruise
  • 3 Nights' Lodging in your choice of over 137 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 the Chicago Grand Tour and two night's lodging.
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Package Includes
  • 2 Nights' Accommodations in your choice of over 137 hotels.
  • Inside Chicago Grand Tour
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 137 hotels.
  • Inside Chicago Grand Tour
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