1 deal from our Canadian site*
* Taxes and fees may be additional.
Travel into February
Major Airlines on Fly.com
 
17 deals from our U.S. site*
* Taxes and fees may be additional.

Deals are priced in U.S. dollars and are sourced by our U.S. Deal Experts. Airfare and air-inclusive vacation or cruise pricing includes taxes; hotel, entertainment, car rental, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

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: 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: Chicago

Chicago hotels, entertainment and free events

Deals into Fall
 
Source: Go Card

Saves on the current cost of the pass online, plus built-in savings over booking separately.

Must be exchanged for a Go Card by March 31, 2015
 
Source: Briar Street Theatre

"Blue Man Group" is a unique theatrical production that features Grammy-nominated live music, comedy and multimedia theatrics

Shows through March 1
 
Source: The Joffrey Ballet

Save up to 40% on the renowned show at Chicago's Auditorium Theatre

Select shows Dec. 5-24
 
Source: The House Theatre of Chicago

Dennis Watkins is "Chicago’s official magic man," according to the Chicago Sun-Times

Select dates through Feb. 28
 
Source: Symphony Hall

Modeled after the traditional New Year's concert in Vienna (Neujahrskonzert), the show features the music of Strauss along with professional dancers.

Sunday, Dec. 28, at 2:30 p.m.
 
Source: Lyric Opera of Chicago

Lyric's previous run of the opera was "a joyous and compelling production," hailed as "the hottest show in town" (Chicago Tribune)

Nov. 26, 28; Dec. 2
 
Source: Intimate Illusions

Ivan Amodei's "Intimate Illusions" visits Chicago over Thanksgiving weekend

Nov. 28, 29 & 30
 
Source: Steppenwolf Theatre Company

"Airline Highway" is written by Pulitzer Prize finalist Lisa D'Amour ("Detroit") and directed by Joe Mantello (“The Last Ship” and “Wicked")

Select dates Dec. 28-Jan. 11
 
 
 
 
 
Into October
Featured Destination: Chicago
 
 
Need to make travel arrangements?
Compare Multiple Travel Sites in One Search
From: To: Travellers:
Depart: Return: One-way
Round-trip   
Enter city: Guests:
Check-in: Check-out: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time:

Compare Hotel Rates

Travelzoo News

Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
Here are some I can no longer live without. More