Featured Destination: Chicago

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Savings in the Windy City

No matter what the season, there are new reasons to fall in love with -- or rekindle love for -- Chicago. Skyscraper views, free events and a flourishing culinary scene are just the beginning for those who time a trip this summer or fall.

Travelzoo Deal Experts have sourced hotel, entertainment and local deals that can save more than 50% on regular prices.

Discover why Chicago has a legacy of churning out some of America's most colorful characters, from the influential (President Barack Obama) to the iconic (Michael Jordan) to the infamous (Al Capone). Before you know it, Chicago will be your kind of town, too.

 
 
 
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Top Deals Handpicked by Travelzoo

 
Redeem by Nov. 12, 2014
Hana Lounge at Westin Chicago River North
 
Select dates in November-December
The Westin Chicago River North
 
 
 
Select dates through Nov. 22
The Westin Michigan Avenue
 
 
 
 
Nov. 23-27; Dec. 14-18, 21-26
Dana Hotel & Spa
 
 
Sept. 15, 2014 - Jan. 15, 2015
The Garage & the Salsa Truck
 
Select dates through December
Sheraton Chicago Hotel & Towers
 
Redeem by Oct. 31, 2014
Chicago's Finest Tours
 
 
 

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