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

Chicago hotels, entertainment and free events

Deals into Fall
 
Source: Inn of Chicago

Unpack at one of the best locations in Chicago -- one block from famed Michigan Avenue -- with stay dates available through fall and winter.

Dec. 7 - March 12; fall dates also available
 
Source: American Airlines

Fly to cities nationwide including New York, Las Vegas, Austin, Miami, Los Angeles, Chicago and more

Select dates through March 4
 
Source: Cathay Pacific

Fly on a 5-star airline from Los Angeles, Chicago or NYC to Tokyo, Osaka, Sapporo, Nagoya, Fukuoka or Okinawa.

Depart through Dec. 9, return by June 9
 
Source: Vacation Express

Escape to a resort located on "one of the best strands in the Bahamas" with one of the lowest Bahamas packages we've seen this year

Select departures, September-December
 
Source: Travel Discounters

Marvel at the pyramids, temples and tombs of ancient Egypt with a trip that saves as much as $950 per person.

Weekly departures through Nov. 30, 2015
 
Source: Vacation Express

Catch whale watching season in Puerto Vallarta, explore Banderas Bay, and relax on a secluded beach with this all-inclusive getaway.

Select November-March departures
 
Source: Virgin America

With these low fares, it's clear why Virgin America holds the title for "Best Low-Cost Airline."

Oct. 7 - Dec. 17
 
Source: Browntrout

Discover "surprising, inspiring" (Zagat) plates at North Center's acclaimed Browntrout. Save over 50% on farm-to-table dinner, including a $50 wine credit.

Sept. 18, 2014 - Nov. 30, 2014
 
Source: Chicago Philharmonic

Tickets are up to 55% off to see “One of the country’s finest symphonic orchestras” according to John von Rhein of the Chicago Tribune.

Sept. 21, 2014
 
Source: The Garage & The Salsa Truck

Savor gourmet tacos and a rotating menu from Chicago's food truck community for 40% off at the Garage, home of the Salsa Truck.

Sept. 15, 2014 - Jan. 15, 2015
 
Source: Shatter Glass Group

Opened in 1987, Shatter Glass Group is the city's first and oldest glass-teaching facility. Utilize those years of experience and save 55% on private classes.

Sept. 15, 2014 - Dec. 30, 2014
 
Source: Xtreme Xperience

Subscribers can save up to 50% off rides and drives in their choice of luxury supercar when the Xtreme Xperience puts you in the drivers seat.

Valid for all Xtreme Xperience 2014 dates
 
Source: Xtreme Xperience

Subscribers can save up to 50% off rides and drives in their choice of luxury supercar when the Xtreme Xperience puts you in the drivers seat.

Valid for all Xtreme Xperience 2014 dates
 
Source: Xtreme Xperience

Subscribers can save up to 50% off rides and drives in their choice of luxury supercar when the Xtreme Xperience puts you in the drivers seat.

Valid for all Xtreme Xperience 2014 dates
 
Source: Xtreme Xperiences

Subscribers can save up to 50% off rides and drives in their choice of luxury supercar when the Xtreme Xperience puts you in the drivers seat.

Valid for all Xtreme Xperience 2014 dates
 
Source: Xtreme Xperiences

Subscribers can save up to 50% off rides and drives in their choice of luxury supercar when the Xtreme Xperience puts you in the drivers seat.

Valid for all Xtreme Xperience 2014 dates
 
Source: Learn Scuba Chicago

CBS Chicago calls Learn Scuba one of the best places to take diving lessons in Chicagoland. Travelzoo subscribers can save over 60% off an intro class.

Sept. 10, 2014 - Nov. 15, 2014
 
Source: Penn's Landing Playhouse

Save up to 50% on tickets to this 'outrageously funny and surprisingly sweet" comedy (Chicago Sun-Times)

Through Sept. 25
 
Source: 'The Last Ship'

The Chicago Sun-Times calls praises the "ravishing score" and "poetic lyrics."

Sept. 8, 2014 - Sept. 30, 2014
 
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Travelzoo Tips

Chris Vassil — Travel, Entertainment and Local Deal Expert
Chris Vassil
Deal Expert, Chicago
Going as a grown-up is just as fun, if not more so, than going at age 6. Here's why. More