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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Additional savings through fall.
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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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