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

Chicago hotels, entertainment and free events

Deals into Fall
Source: Hilton Chicago

Ideally located along famed Michigan Avenue, this 4-star hotel is the perfect home base for exploring Millennium Park and the museum campus.

Select dates Dec.-Feb.; Nov.-April also discounted
Source: Hard Rock Hotel Chicago

Marvel at music memorabilia at this 4-star hotel that is walking distance from the Mag Mile shopping and the theater district.

Travel daily through February
100% (14 ratings)
Source: Travel Discounters

This trip includes excursions that often cost extra with other tour operators. Departures from major cities nationwide.

Weekly departures through November 2015
Source: Gate 1 Travel

Explore the storied country where East meets West on a luxe 11-night vacation, including upscale hotel stays for the lowest price we've seen this year

February-March departures
Source: Great Value Vacations

This package -- including roundtrip air, car and six nights at 4- and 5-star castle hotels and spas -- saves up to $475 per person.

Select dates January-May
Source: Indus Travels

This vacation includes three of Latin America's most popular destinations at a cost-effective price.

Feb. 19; Sept. 23; surrounding dates +$500
Source: Indus Travels

Highlights of this "bucket list" trip include a sunrise tour to Taj Mahal and Dubai's Gold Souk.

April 2, Sept. 17; other dates from +$300
Source: CheapCaribbean.com

Winter may have rolled in early this year, but here's a chance to leave it behind with a 4-star, all-inclusive vacation to Cancun

Select dates January-April
Source: Oceania Cruises

Depending on itinerary, sail to exotic ports in China, Japan, Thailand, Vietnam and Singapore. This deal includes tips, air, $500 credit & more.

Depart Feb. 21; March 10; +$500 March 26
Source: Odyssey Cruises

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

Jan. 5, 2015 - June 30, 2015
Source: Guitar Cities

CBS Chicago praises the "effective, friendly instructors" at Guitar Cities Chicago. With this offer, receive four private lessons for 65% off.

Through March 31, 2015
Source: Chuck's: A Kerry Simon Kitchen

With a new menu from celebrity chef Kerry Simon and his brother, executive chef Scott Simon, subscribers can save 40% on a downtown dinner for two.

Dec. 8, 2014 - June 8, 2015
Source: Red Door

Featuring "top notch comfort food" (Thrillist) and a "solid beer list" (Zagat), Red Door opens its doors to subscribers who can save 40% off food and drinks.

Jan. 3, 2015 - May 1, 2015
Source: Tiffani Kim Institute

Subscribers can save nearly 55% on their choice of massage and facial at the Tiffani Kim Institute, a three-story urban River North spa escape.

Dec. 26, 2014 - June 26, 2015
Source: The Everly Spa

With over a decade of experience as an aesthetician, owner Kelli Komar has earned accolades from Allure magazine for her facial treatments.

Nov. 20, 2014 - May 20, 2015
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 subscribers a luxe dinner for two.

Jan. 2, 2015 - March 31, 2015; closed Sundays
Source: International Museum of Surgical Science

"One of Chicago's most interesting and least famous museums, the International Museum of Surgical Science is a true gem" (USAToday's 10Best.com).

Through May 20, 2015; closed Mondays
Source: Imagine Lifestyles

Save up to 60% on a "once-in-a-lifetime experience" to drive the "best cars in the world" (Travelzoo users) at one of Imagine Lifestyles' upcoming 2015 events.

Select 2015 dates through Aug. 29, 2015
Source: Tall Ship Red Witch

Set a course for Lake Michigan adventure this summer and reserve a trip on the Tall Ship Red Witch. Cruises in 2015 start at $17, the best prices we've seen.

Beginning of sailing season through July 31, 2015
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Travelzoo Tips

Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
Several hotel chains, including Hilton and Choice Hotels, offer discounts for active More