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

Chicago hotels, entertainment and free events

Deals into Fall
Source: The Westin Michigan Avenue

This 4-star hotel is close to the city's best shopping and dining.

Select dates Nov. 23 - Jan. 10
Source: Omni Chicago

Stretch out in a suite at a AAA 4-Diamond hotel on Chicago's famed Michigan Avenue.

Daily Oct. 26 - Jan. 31
Source: Doubletree Hotel Chicago Magnificent Mile

Explore Chicago's "urban playground" while saving 40% on current prices.

Select dates through March 2015
100% (2 Ratings)
Source: Travel Discounters

This tour includes an excursion to Abu Simbel, which is typically an additional cost for travellers.

Weekly departures through Nov. 30, 2015
Source: CheapCaribbean.com

The formula for an unforgettable trip lies in Jamaica's "white-sand beaches, year-round sunshine, misty mountains, lush rainforest and superb coffee."

Select departures October-March
Source: Lion World Travel

Sample the best of Cape Town and South Africa's exotic wildlife with a seven-night luxury vacation, including stays at a 5-star hotel and lodge.

Select dates January-December
Source: The Magic of Ivan Amodei

Setting up in the Ritz-Carlton Chicago, master illusionist Ivan Amodei brings "Intimate Illusions" to Chicago over Thanksgiving weekend. Tickets to this Los Angeles Times "top pick" are now 50% off.

Nov. 28-30
Source: Grapes to Bottles

Sample dozens of different wines at your choice of two autumn events from the Grapes to Bottles team at the Dana Hotel.

Nov. 22 or Dec. 13, 2014
Source: Giordano Dance Chicago

The program will include two world premieres: “Exit 4,” a full-company work by choreographer Roni Koresh, and “Moving Sidewalks,” by Autumn Eckman, Giordano Dance’s assistant artistic director and resident choreographer.

Oct. 24-25
Source: The House Theatre of Chicago

The House Theatre of Chicago's annual holiday favorite "The Nutcracker: a Magical Play for Christmas" is back at Chopin Theatre. Travelzoo subscribers can save 40% on tickets to the "moving, family-friendly, richly imaginative" play (The Chicago Tribune).

Select performances Nov. 6-Dec. 7
Source: Blue Man Group

"Blue Man Group" at Briar Street Theatre in Chicago is now offering Travelzoo subscribers an exclusive deal that saves $15 on performances through March 1.

Through March 1
Source: Trattoria Isabella

Metromix likes the "hearty portions" of "must try" appetizers and says "it's tough to choose" between Trattoria Isabella's Sicilian-focused entrees.

Oct. 13, 2014 - Jan. 13, 2015; Sunday-Thursday only
Source: Pazzo's @ 101

Dine with a view of the Lyric Opera building at Pazzo's @ 101, a 4-star OpenTable destination. Subscribers can save 35% on dinner.

Oct. 13, 2014 - Jan. 13, 2015; closed Sundays
Source: Steppenwolf Theatre Company

Tickets are now 50% off select performances to the "highly recommended" (Chicago Sun-Times), "raw and beautiful" (Chicago Tribune).

Select dates Oct. 9-Nov. 12
Source: Sun Aero Helicopters Inc.

CBS Chicago says a skyline tour with Sun Aero Helicopters is one of the city's best. Subscribers can save over 40% off a flight.

Oct. 10, 2014 - April 30, 2015
Source: Chicago's Finest Tours

Our subscribers love Chicago's Finest Tours; one said, "As a lifelong resident I have been on many tours but this one was a must do for every visitor."

Nov. 1, 2014 - May 31, 2015
Source: Whisk Chicago

Inspired by noted carnivore Ron Swanson, Whisk "mixes burgers and pancakes in a way that would make the Parks and Rec character proud" (Chicago mag).

Oct. 6, 2014 - March 6, 2015; not valid Sundays
Source: Raymi Productions Chicago

Praised as an "upscale ... elegant bash" by Examiner.com, this year's Masquerade Extravaganza makes tickets available to subscribers for nearly 40% off.

Oct. 31, 2014, between 7-9 p.m.
Source: Cook Au Vin

Get ready to knead, toss and mix your way to better baguettes and baked goods with a class from Cook au Vin, which earns 4.5 stars on Yelp.

Oct. 1, 2014 - April 1, 2015
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Travelzoo Tips

Stephen Aviano — Travel, Entertainment and Local Deal Expert
Stephen Aviano
Deal Expert, New York
Take frame-worthy vacation shots with these tips from our photo pro. More