117 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Sheraton Chicago Hotel & Tower

Take in skyline views from a 4-star Chicago hotel that puts guests in the middle of the downtown action.

Many dates Nov. 22 - Jan 31
 
Source: The Westin Michigan Avenue Chicago

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.

Many dates Nov. 22 - March 28
 
Source: Broadway in Chicago

Save up 35% on premium seats to to the Chicago Broadway premiere of the Tony winning musical 'Pippin' at the Cadillac Palace Theatre.

Select shows July 29 - Aug. 9
 
Source: Major Airlines on Fly.com

Fly from Atlanta, Chicago, NYC & more.

August-November
 
Source: CheapCaribbean.com

Sunset cruises, scuba diving and greens fees are all part of this resort's all-inclusive package

Select departures August-October
 
Source: Great Value Vacations

Soak up the Irish countryside from a villa at a 5-star resort recently named one of the Best Resorts in Europe by Conde Nast Traveler readers

Select dates October 2015 - March 2016
 
Source: Indus Travels

Visit the great pyramids and their guardian Sphinx on this seven-night fully guided tour, that includes most meals, taxes, and a five-star hotel stay.

Oct. 6; Nov. 10; May 3
 
Source: Travel Discounters

This bucket-list destination tour includes air and taxes, and offers a unique itinerary that promises both value and quality for 11-nights.

Weekly departures from Aug. 2015 through Nov. 2016
 
Source: African Travel, Inc.

Delight in a bucket-list trip with safari game drives and a World's Best Hotel

November-March departures
 
Source: Lion World Travel

This 5-star trip has air from 38 U.S. cities and perks like wine tastings and thrilling game drives

September 2015-December 2016 departures
 
Source: Megabus

Snag a comfortable, budget-friendly and convenient alternative to trains or driving with this deal.

August
 
Source: Avis / Budget

This deal is available at all popular U.S. destinations through the end of the year.

Through 2015
 
Source: EuropeanDestinations.com

This two-city Central Europe trip is the lowest-priced independent package we've seen in years.

August-November departures; more dates available
 
Source: The Laguna Playhouse

Jake and Elwood head to Laguna Beach this summer to perform "The Official Blues Brothers Revue," a live concert show featuring comedy and hit songs from the original movie. The Chicago Sun-Times said it has "infectious and unbridled energy ... it blows the roof off." Tickets are now half off.

August 13-23
 
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: Cirque du Soleil

With this deal, save up to 15% on tickets to "Kurios - Cabinet of Curiosities," including prime weekend performances.

July 31, 2015 - Aug. 16, 2015
 
Source: Navy Pier

Celebrate summer in Chicago at Navy Pier's first-ever outdoor movie nights with classic films, including "Ferris Bueller's Day Off" and "Jaws."

Through Sept. 30, 2015; Thursdays
 
Source: Scoot for Good

Take a tour of Chicago's downtown or northern neighborhoods with Scoot for Good, an organization pairing charitable giving with two-wheeled fun.

Through Oct. 30, 2015
 
Source: Bliss San Francisco

Visit SoMa for a relaxing day at Bliss San Francisco and save 50% on your choice of massage or facial.

Through Sept. 30, 2015
 
Source: Bliss Los Angeles

Head to the W Los Angeles - West Beverly Hills for a relaxing spa day at Bliss with your choice of massage or facial at 50% off.

Through Sept. 30, 2015; Monday-Friday
 
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

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More