123 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: Friendly Planet Travel

Depart from the U.S. on Emirates and continue the trip with 5-star hotels and a memorable itinerary including visits to the Taj Mahal and Burj Khalifa

February - April departures
 
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: Apple Vacations

Spend a week away from the winter cold with this all-inclusive vacation package that includes a stay at a water park resort

Select departures in January
 
Source: Vacation Express

Warm up this winter with four nights at a beachfront, all-inclusive Cancun resort including flights

Select January-April departures
 
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: 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: 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
 
Need to make travel arrangements?
Compare Multiple Travel Sites in One Search
From: To: Travelers:
Depart: Return: One-way
Round-trip   
Enter city: Guests:
Check-in: Check-out: Rooms:
From: To: Travelers:
Depart: Return: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time:

Compare Hotel Rates

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