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

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These Destination of the Week Deals are no longer available, but you can check our latest Destination of the Week or visit one of our travel deals categories including flights, hotels, cruises, vacations and local deals.


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