81 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Major Airlines on Fly.com

Fly from Tampa, Chicago, Louisville and more

Travel into July
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.

Select dates through July 3
Source: The Westin Chicago River North

Check in to a AAA 4-Diamond hotel with a top location and sweeping views of the Chicago river.

Select dates through Aug. 29
Source: Hotel Lincoln

Take on Chicago like a local at a boutique 4-star hotel, located in the city's posh Lincoln Park neighborhood.

Most Sundays-Thursdays through Aug. 27
Source: 'Chicago The Musical' on Broadway

Save up to $50 on the Tony- and Grammy award-winning tale of fame, fortune and "All That Jazz."

Through June 29
Source: 'Cuff Me!'

Tickets are more than 60% off for the musical comedy "Cuff Me!"

Through April 26
Source: Major Airlines on Fly.com

Fly from Boston, Chicago, San Francisco & more

Into July
Source: Major Airlines on Fly.com

Fly from San Francisco, Los Angeles, Chicago & more

Into July
Source: Major Airlines on Fly.com

Fly from NYC, Los Angeles, Chicago & more

Into July
Source: 'Rose and the Rime'

"Rose and the Rime" opens this month in the Carnival Studio Theater

April 23, 24 & 26
Source: The Apartment

"Girls Night: The Musical" follows five friends during a wild and outrageous night out, and subscribers can save up to 60% on tickets.

Select dates May 2 - June 14
Source: Bottlenotes

Swirl & sip wines from California, Spain, France, Italy, New Zealand and Brazil during "Around the World in 80 Sips" at the Museum of Contemporary Art

Friday, May 9
Source: Hertz

Hit the open road with car rentals in cities from coast to coast

Through April
Source: Lyceum Theatre

Save 25% on tickets to this "convulsively funny" show (Variety).

April 23 - May 25
Source: 'Defending the Caveman'

This long-running comedy comes to the City Theatre, and tickets are 45% off.

May 15-25
Source: Bottlenotes

Swirl, sip and savor international wines during the tasting event "Around the World in 80 Sips" at the Museum of Contemporary Art in Chicago, and save 50% on tickets.

April 17, 2014 - May 8, 2014
Source: Rittergut Wine Bar & Social Club

Save over 50% on wine flights paired with gourmet charcuterie and cheese at this riverside hideaway, named one of the city's best wine bars by CBS Chicago.

April 14, 2014 - Sept. 4, 2014; closed Sundays; not available on Saturdays after May 24
Source: Theory

Travelzoo subscribers can save up to 59% off lunch or brunch at this award-winning "modern sports-focused lounge" (Metromix) in River North.

April 15, 2014 - July 15, 2014; brunch served Saturday-Sunday, lunch Monday-Friday
Source: Chicago's Finest Tours

Step inside the Chicago Pedway and learn about the city with Chicago’s Finest Tours, which earns a 5-star TripAdvisor rating from more than 275 reviews.

Jan. 14, 2014 - May 31, 2014
Source: TourBound Golf Academy

Tee off without leaving the Loop at TourBound Golf Academy, led by Golfweek-praised instructor Scot W.R. Nei. Subscribers save nearly 70% on a lesson.

April 11, 2014 - Aug. 11, 2014
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Andrew Young — Travel, Entertainment and Local Deal Expert
Andrew Young
Deal Expert, New York
Summer is coming. Our thoughts turn to beaches, grilling meats and summer vacation. More