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: 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: 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: 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: Pizzeria UNO

Pizzeria UNO is where Chicago's iconic deep dish pizza was created over 70 years ago. With this exclusive offer, members can learn to craft their own.

Through Aug. 31, 2016; Tuesday-Sunday mornings
98% (183 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% (210 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% (55 ratings)
 
Cheap Roundtrip Fares to Chicago from:
(Per person, including taxes and fees. Click a price to verify availability now.)
fly.com
more cities
close close
Don’t see your city listed above? Search for flights to Chicago:

Still looking for your flight?
Try Fly.com, a new airfare search engine from





Compare Hotel Rates