61 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Fairmont Chicago

Members can save big on a holiday trip to "one of the Loop's most popular hotels" (Travel + Leisure) over select dates through Valentine's Day 2017.

Select dates through February 2017
 
Source: Kimpton Hotel Monaco Chicago

Score a great rate just steps from the Mag Mile, the Chicago River and the Loop at one of the best hotels in Chicago: the AAA 4-Diamond Hotel Monaco.

Travel through Jan. 31
100% (52 ratings)
 
Source: Central Loop Hotel

While other Chicago hotels charge as much as $250 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% (19 ratings)
 
Source: FirstMerit Bank Pavilion at Northerly Island

Save up to 50% on tickets and hear hits like "Worth It," "Work From Home" and "Sledgehammer"

Wednesday, Aug. 31, at 7 p.m.
 
Source: United & American Airlines on Fly.com

September-December
 
Source: Wrigley View Rooftop

Save up to 30% on tickets to see the Chicago Cubs from a rooftop with all-you-can-eat food and drinks, including beer and wine.

Select dates through Sept. 4, 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)

Sept. 13 - Dec. 14
 
Source: Seadog Cruises

Race across the waters of Lake Michigan this summer, or take an architectural cruise down the Chicago River with the top-rated Seadog Cruises team.

Through Sept. 30, 2016
 
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.

Aug. 15, 2016 - Feb. 28, 2017
 
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 Oct. 31, 2016
 
Source: The Metropolitan Club of Chicago

Arguably the greatest view from a restaurant in North America, the exclusive Metropolitan Club in the Willis Tower offers members a luxe dinner for two.

June 20, 2016 - Oct. 1, 2016
93% (2020 ratings)
 
Source: Odyssey Cruises

Save over 40% on a dinner cruise on Odyssey Chicago, a cruise which earns a 4-star rating from TripAdvisor users.

Through Aug. 31, 2016
98% (49 ratings)
 
Source: City Winery

Dine at City Winery in the West Loop, "a multifaceted amalgam of all things wine from drinking it to making it" (Zagat), and save 50% on brunch, lunch or dinner.

Through Sept. 15, 2016; Sunday-Thursday
89% (542 ratings)
 
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
 
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% (335 ratings)
 
Source: Mystic Blue

Save over 30% on a two-hour Boathouse cruise on Mystic Blue this summer.

June 20, 2016 - Aug. 30, 2016
98% (49 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: Oxygen Spa Studio

Our members praise their trips to Oxygen Spa Studio in the West Loop -- 97% of nearly 200 Travelzoo members loved their treatments.

Through Aug. 31, 2016
97% (211 ratings)
 
Source: Wateriders

Members save 40% on a fireworks kayak tour from Wateriders that's "a truly one-of-a-kind sightseeing experience" (Travel + Leisure).

Through Sept. 3, 2016; Wednesdays or Saturdays
86% (87 ratings)
 
Source: Chuan Spa at The Langham, Chicago

Save 50% on a luxurious spa package at Chuan Spa at The Langham -- named one of the Best Spas in Chicago by Travel + Leisure.

June 1, 2016 - Aug. 31, 2016; Monday-Thursday
98% (56 ratings)
 
Cheap Roundtrip Fares to Chicago from:
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