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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 an Chicago getaway on the shores of Lake Michigan!

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Most Popular Packages     

Gather round, m'lords & ladies, for the Medieval Times Dinner Tournament Package in Chicago, which includes tickets to the hottest dinner theater show around, your choice of a Windy City sightseeing tour, and three nights lodging in the hotel of your choice.
Package Includes
2 or More Nights Hotel Accommodations
Medieval Times Dinner & Tournament - Schaumburg, IL
Choice of 1 Sightseeing Tour
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With the Two Night Spirit of Chicago Cruise Package, you'll enjoy a spectacular dining & entertainment cruise around the Windy City waterfront, as well as two nights lodging at the Chicago hotel of your choice.
Package Includes
2 or More Nights Hotel Accommodations
Choice of 1 Spirit of Chicago Cruise
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Get ready to ride the rails with a great family friendly vacation package to Six Flags Great America where you can enjoy the thrill of the roller coasters and admission to Hurricane Harbor while you spend 2 nights at the hotel of your choice.
Package Includes
2 or More Nights Hotel Accommodations
Six Flags Great America, Chicago
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You'll have the chance to see the beautiful city of Chicago, Illinois from a yacht and from a motorcoach during your Land and Lake Chicago Experience.
Package Includes
2 or More Nights Hotel Accommodations
Land and Lake Tour
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With the Chicago Sightseeing Weekend Getaway you'll find two nights' lodging and your choice of sightseeing tour from a list of varying options for a complete weekend of experiencing the sights of the Windy City.
Package Includes
2 or More Nights Hotel Accommodations
Choice of 1 Sightseeing Tour
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Enjoy the best of the Chicago blues music scene with the Chicago Blues Experience Weekend Getaway, which includes your choice of the ultimate blues experience and two or more nights of lodging at your choice of hotel.
Package Includes
2 or More Nights Hotel Accommodations
Choice of 1 Blues Experience
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Take some time away from home to visit Chicago's famous Macy's State Street shopping area extravaganza!
Package Includes
2 or More Nights Hotel Accommodations
Macy's State Street Shopper
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A great way to enjoy the sights of the city, the Chicago Vacation Getaway Touring Package offers you an indepth look at the Windy City along with three nights of lodging in the area.
Package Includes
3 or More Nights Hotel Accommodations
Field Museum plus South Shore Tour
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With so much to see in Chicago and so little time to take it all in, it may be best to break your sightseeing into sections.
Package Includes
2 or More Nights Hotel Accommodations
North Side Tour - Chicago, IL
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Experience the most popular attractions in the Windy City with the Best of Chicago Comprehensive Package, which includes the multi-attraction pass of your choice, plus your choice of one river cruise, one sightseeing tour, and five nights lodging in the hotel of your choice.
Package Includes
5 or More Nights Hotel Accommodations
Choice of 1 Sightseeing Cruise
Choice of 1 Sightseeing Tour
Choice of 1 Multi-Activity Pass
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There's plenty to see in Chicago, and you won't miss any of it with the Windy City Sightseeing Adventure, which includes the Grand Tour & Sears Tower Tour, your choice of one river & lake cruise, your choice of an additional sightseeing tour, and four nights lodging at the hotel of your choice.
Package Includes
2 or More Nights Hotel Accommodations
Inside Chicago: Grand Tour & Sears Tower - Chicago, IL
Choice of 1 Sightseeing Cruise
Choice of 1 Sightseeing Tour
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Enjoy admission to the top attractions in the Windy City with the Go Chicago Attraction Pass Package, which includes a 2-Day Go Chicago Card, your choice of one sightseeing tour, and three nights lodging in the hotel of your choice.
Package Includes
3 or More Nights Hotel Accommodations
2 Day Go Chicago Card
Choice of 1 Sightseeing Tour
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Get away from the hassle of everyday life with the Quick Chicago Weekend Getaway, which includes a sightseeing tour, cruise, and two nights lodging in the hotel of your choice.
Package Includes
2 or More Nights Hotel Accommodations
Choice of 1 Sightseeing Cruise
Choice of 1 Sightseeing Tour
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Treat your sweetie to a trip to Chicago to sail the blue waters on the Chicago Odyssey.
Package Includes
2 or More Nights Hotel Accommodations
Choice of 1 Chicago Odyssey
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All prices are in US Dollars
         

 
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