Featured Destination: Chicago

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Savings in the Second 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

Dec. 7 - March 12; fall dates also available
Inn of Chicago
Select dates in November-December
The Westin Chicago River North
Travel into December
Major Airlines on Fly.com
Valid through Oct. 31, 2014
Chicago's Finest Tours
Redeem by Sept. 30, 2014
The Metropolitan Club of Chicago
Select dates through Nov. 22
The Westin Michigan Avenue
Select dates through December
Sheraton Chicago Hotel & Towers
Through Sept. 28
Briar Street Theatre

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Depart: Return: One-way