46 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Central Loop Hotel

While other Chicago hotels charge $250 or more in fall, Central Loop Hotel dodges the trend, undercutting many of them by as much as $100

Weekends Aug. 19 - Nov. 26; Dec. is even cheaper
95% (20 ratings)
 
Source: Joffrey Ballet

Tickets start at just $33 per show for orchestra seats.

Various dates 2016-2017
 
Source: American & United Airlines on Fly.com

October-January
 
Source: Chicago Trolley & Double Decker Co.

These open-top, double-decker buses earn a 4-star rating from both TripAdvisor and Yelp users and transport riders through Chicago with guided narration.

Through Dec. 31, 2016
 
Source: Virgin America

Snag discounted fares on the 'Best Domestic Airline' for the ninth year in a row (Travel + Leisure World's Best Awards)

Oct. 18 - Dec. 14
 
Source: Virgin America

Grab a seat for summer and jet across the country on the 'Best Domestic Airline.'

Oct. 18 - Dec. 14
 
Source: JetBlue Airways

Oct. 11 - Jan. 24
 
Source: Journeyou.com

This comprehensive 14-night itinerary includes visits to Santiago, Torres del Paine National Park, Puerto Natales and Buenos Aires.

Daily departures
 
Source: Skydeck Chicago

Soar to the top of one of America's tallest buildings and see Chicago from 103 stories above street level with this offer that saves over 20% on admission.

Through Feb. 28, 2017
 
Source: Pinstripes

Save over 40% on drinks and food at Pinstripes, a bocce, bowling and bistro hub with four locations across the Chicagoland area.

Through Nov. 10, 2016; Sunday-Thursday
94% (33 ratings)
 
Source: Chicago Explorer Pass

Get a taste of all Chicago has to offer, and save up to 40% on the gate prices to over 25 of the city's top attractions with the Chicago Explorer Pass.

Valid for use through March 31, 2017
85% (348 ratings)
 
Source: Museum of Contemporary Art Chicago

Travelzoo members save 25% on admission to the Museum of Contemporary Art, one of Chicago's best museums, according to Chicagoist and Time Out.

Through May 31, 2017
 
Source: Chicago Botanic Garden

Save 30% on a ticket to Chicago Botanic Garden's Night of 1,000 Jack-o'-Lanterns -- the only event of its kind in the Chicagoland area.

Oct. 20-23, 2016
 
Source: Balanced Flow Wellness at Balance Spa - Palmer House A Hilton Hotel

Fodor's praises the "massive" AAA 4-Diamond Palmer House for its prime downtown location and "modern attributes" like the luxurious spa.

Through Nov. 11, 2016
 
Source: Balance Spa & Fitness at Palmer House A Hilton Hotel

Spend a full day at the spa at the AAA 4-Diamond Palmer House -- take your pick of manicure, pedicure and/or facial package plus all-day amenity use.

Through Nov. 11, 2016
 
Source: Meals on Wheels Chicago

The Meals on Wheels Chicago Celebrity Chef Ball is “always one of the most spectacular” culinary events of the year (Chicagoist), and the only way to get a coveted ticket for the 2016 Chef's Tasting Party is through Travelzoo.

Friday, Oct. 21, 2016, 8:30 p.m.–12:30 a.m.
 
Source: Pops for Champagne

"Those who worship the bubbly agree there's no substitute for this first-class purveyor of grand Champagne" (Zagat). Save over 40% on a visit to Pops.

Through Oct. 31, 2016; Sunday-Thursday
 
Source: Stetsons Modern Steak + Sushi

Travelzoo members rave about Stetsons, calling this "hidden gem" a "must when downtown" for "one of the best steaks you will ever eat." Save 50% on dinner.

Oct. 1, 2016 - Dec. 30, 2016
97% (333 ratings)
 
Source: Inside Chicago Walking Tours

Save over 30% on your choice of walking tour at Inside Chicago Walking Tours, which earns a perfect 5-star rating from TripAdvisor and Yelp users.

Through Dec. 31, 2016
 
Source: Chuan Spa at The Langham, Chicago

For this month only, save over 60% on a spa day pass at Chuan Spa at The Langham -- named one of the Best Spas in Chicago by Travel + Leisure.

Sept. 1, 2016 - Sept. 29, 2016; Monday-Friday
93% (72 ratings)
 

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