Affordable Chicago Vacation Packages

Departing From: See the Top

See the Top
  • Popular picks
  • 4 & 5 Star Vacations
  • Vacations under $500
  • Vacations Under $1000
  • 3 & 4 Night Vacations
  • 7 to 10 Night Vacations


See the Top
  • Popular picks
  • 3 & 4 Night Vacations
  • 7 to 10 Night Vacations
  • Vacations under $500
  • Vacations Under $1000
  • 4 & 5 Star Vacations
Feb 23 - 27
You Save $ 88
$ 547  $ 459
per person
 
Hard Rock Hotel Chicago
#2 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Feb 23 - 27
You Save $ 93
$ 715  $ 622
per person
 
 
* Prices are in USD for one adult based on double occupancy and include tax recovery charges. Sample prices were found recently by Travelocity or its customers. Our real-time dynamic packaging engine is constantly updating prices and availability. Please click prices for current information.
 
 

All About Chicago

Choose From Fun Chicago Vacation Packages in the Windy City

Chicago is a city with a unique soul. Its proud imperial skyline, sophisticated cultural scene, and lively and distinctive restaurants can leave even the most hard-to-please tourists dazzled during their Chicago vacations. Located in the Midwest, the city famously dyes its namesake river green to mark St. Patrick’s Day and proudly embraces its tough-guy past: the rough-and-tumble “Chicago Way.”

History buffs with an eye for architecture should include the Loop in their Chicago vacation plans. This area, south of the river, is steeped in rich history and reminiscent of 19th century Chicago. Just to the north, on the other side of the river, the Magnificent Mile is home to Chicago hotels and upscale shopping boutiques that rival anything you’d find along New York’s Fifth Avenue.

There’s so much to do here, and with Chicago vacation packages, tourists can take in a show, stroll through the Chicago Botanic Garden, learn about art and history in the museums, or watch a game at Wrigley Field. Business travelers also book cheap flights to Chicago regularly since it is home to many companies’ corporate headquarters.

As the transportation hub of the Midwest, Chicago remains a magnet for immigrants, young people starting their careers, as well as those just coming for a Chicago vacation. The Lincoln Park community, just a short walk from Lake Michigan, encompasses several neighborhoods and is one of the more gracious, gentrified areas you’ll find in Chicago. These neighborhoods, like River North, have a high concentration of art galleries, drawing young students, professionals, and other urbanites.

 
 

Enjoy Your Chicago Vacation

Room Adults
(18-64)
Minors
(2-17)
Seniors
(65+)
Room 1
 

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