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

Through January
Source: The Gwen, A Luxury Collection Hotel

Starwood's first Luxury Collection hotel in Chicago is just steps from famous shops and restaurants

Travel through March 31
Source: Major Airlines on Fly.com

Select dates through January
Source: Virgin America

Virgin America has been voted Best U.S. Airline in Condé Nast Traveler's Readers' Choice Awards.

Oct. 31 - Feb. 28
Source: The Westin Michigan Avenue

Deals heat up when Chicago cools down -- members can save hundreds on a stay at this 4-Diamond spot during winter months.

Most dates Dec. 13 - Feb. 6
Source: The Drake Hotel

Save hundreds on a stay at the Drake, which has been on the itinerary of world leaders and international celebrities for decades.

Dec. 6 - March 4
Source: Skydeck Chicago

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

Through Dec. 31, 2015
Source: Randolph Street Market

With dozens of vendors offering antiques, clothing, global goods and gourmet foods, Randolph Street Market is one of the nation's top shopping destinations.

Through Dec. 13, 2015; valid for events on specific dates
Source: Spirit of Chicago

Set sail this summer on "the largest and most luxurious of the boats that dock along ... Navy Pier" (CBS Chicago). Members save 40% on a dinner cruise.

Through Nov. 30, 2015
Source: Chicago's Finest Tours

Our members love tours from Chicago's Finest, telling us "I enjoyed everything about the tour" and "Our guide was wonderful". Save 50% off a tour this summer.

June 1, 2015 - Oct. 31, 2015
Source: IPO Restaurant

Kick off your weekend with brunch and cocktails in the heart of the Loop at IPO in the W Chicago. Save 50% at this chic spot with an open menu and cocktails.

Aug. 15, 2015 - Nov. 29, 2015; Saturdays & Sundays
Source: Old Fifth

RedEye says Old Fifth, featuring a "dynamic duo" of pizza and whiskey, "should be at the top of your list" for pies made with a "sweeter sauce with a bit of spice."

Through Oct. 31, 2015
Source: Balance Spa & Fitness at Palmer House a Hilton Hotel

Fodor's praises the "bustling and massive" AAA 4-Diamond Palmer House for its "hard to beat" location and "modern attributes" like the luxurious Balance Spa.

Through Dec. 11, 2015; Monday-Friday
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
Source: CityPASS Chicago

Get a taste of all Chicago has to offer and save 50% on admission to the city's top attractions.

Valid 9 days; redeem between March 1, 2015, and Feb. 29, 2016
Source: mEAT - Streeterville

Carnivores, take note -- members can order anything off the menu at the appropriately named mEAT in Streeterville and save over 40%.

Through Nov. 18, 2015
Source: Usagi Ya Sushi

The 2013 Michelin Guide says that the Usagi Ya menu "shines with its unorthodox combinations." Members save more than 50% on this four-course dinner.

Through Nov. 10, 2015
Source: Uptown Underground

Save over 50% on a night out at Uptown Underground, a "subterranean hang that features decorative nods to Prohibition" (Zagat).

Through Oct. 30, 2015
Source: Chicago Water Sport Rentals

Get out on Lake Michigan this summer. Travelzoo members can paddle over the waves or roar across the water on a Jet Ski for 50% off with this offer.

Through Oct. 30, 2015
Source: Willow Crest Golf Club at Oak Brook Hills Resort

Take in the brisk fall weather and save over 40% on a round for two at Willow Crest Golf Club, which earns 4.5 stars from GolfNow users.

Through April 30, 2016
Cheap Roundtrip Fares to Chicago from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Travelzoo Tips

Haifa Sweeny — Travel, Entertainment and Local Deal Expert
Haifa Sweeny
Deal Expert, San Francisco
There are still plenty of great fares if you're strategic about finding them. More