66 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: State House Inn, an Ascend Collection hotel

Save over 50% at this member-favorite hotel with midcentury-modern style; it's a great destination for a Springfield stay full of history.

Daily through Sept. 30, 2016
96% (1609 ratings)
 
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 $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% (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: Hawthorne Race Course

Take in harness races at Chicago's oldest sports facility, Hawthorne Race Course. This ticket package to the Night of Champions races includes access to a private party area, complete with a food and drink buffet.

Saturday, Sept. 10
 
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: State House Inn

This hotel with midcentury-modern style is a great destination for a Springfield stay full of history, and a true member favorite. Members save over 50% on a visit including passes to the nearby Lincoln Presidential Museum and Library.

Daily through Sept. 30
96% (1609 ratings)
 
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: 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: 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: Medieval Times

Dine like royalty on a four-course feast and save over 40% with this offer for the jousting and sword-fighting show at Medieval Times in Schaumburg.

Through Sept. 30, 2016
97% (351 ratings)
 
Source: Kohler Waters Spa at Burr Ridge

Save 35% on a luxurious spa day at Kohler Waters Spa in Burr Ridge -- named one of the Best Day Spas in Chicago by Chicago Magazine.

Through Aug. 31, 2016; not valid Saturdays
96% (28 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)
 
Cheap Roundtrip Fares to Chicago from:
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