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 spring or summer.

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.

Hotel Deals
Additional savings through spring.
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Show Deals
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Spa & Dining Deals
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Top Deals Handpicked by Travelzoo

Valid through Oct. 31, 2014
Chicago's Finest Tours
Redeem by Oct. 30, 2014
The Spa at The Ritz-Carlton
Through Sept. 28
Briar Street Theatre

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