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!
Get started creating your custom vacation package.
Create Your Custom Package
1 Arrival Date
Month: Day:
2 Lodging Options
Nights: Rooms:
3 How many People?
Adults: Children:
Chicago, IL Vacation Packages
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!
Book Now
Package Includes
  • 4 Nights' Lodging in your choice of over 131 hotels.
  • Medieval Times Dinner & Tournament
  • 3-day Go Chicago Card
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!
Book Now
Package Includes
  • 3 Nights' Lodging in your choice of over 131 hotels.
  • Chicago CityPASS
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!
Book Now
Package Includes
  • 3 Nights' Lodging in your choice of over 131 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!
Book Now
Package Includes
  • 3 Nights' Lodging in your choice of over 131 hotels.
  • Six Flags Great America
  • Six Flags Hurricane Harbor
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!
Book Now
Package Includes
  • 4 Nights' Lodging in your choice of over 131 hotels.
  • Big Bus Chicago 3 Day Hop On Hop Off Pass
  • Medieval Times Dinner & Tournament
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.
Book Now
Package Includes
  • 2 Nights' Lodging in your choice of over 131 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.
Book Now
Package Includes
  • Big Bus Chicago 1 Day Hop On Hop Off Pass
  • 2 Nights' Lodging in your choice of over 131 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.
Book Now
Package Includes
  • 4 Nights' Lodging in your choice of over 131 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.
Book Now
Package Includes
  • 2 Nights' Accommodations in your choice of over 131 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.
Book Now
Package Includes
  • Six Flags Great America
  • 2 Nights' Accommodations in your choice of over 131 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.
Book Now
Package Includes
  • 2 Nights' Lodging in your choice of over 131 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.
Book Now
Package Includes
  • Chicago Dinner Cruise
  • 3 Nights' Lodging in your choice of over 131 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.
Book Now
Package Includes
  • 2 Nights' Accommodations in your choice of over 131 hotels.
  • Inside Chicago Grand Tour
Didn't Find What You Were Looking For?
Build Your Custom Package

Date
Nights
Rooms
Adults
Children
START BUILDING YOUR CUSTOM VACATION PACKAGE!
Checkout
Cart
Contact Customer Service at
800-987-9852
Secure Online Payment Options
credit card logos