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
88% (9 Ratings)
 
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: Sinorama Holidays

Beijing, Shanghai, Hong Kong and Macau are some of the highlights of this escorted tour that explores China by boat, rickshaw, coach bus and foot.

Select March, April and November 2015 dates
 
Source: Vacation Express

Book early for winter travel during what USA Today calls the best time to catch prime weather.

Select January-April departures
 
Source: Chicago Symphony Orchestra

The exciting performances include The Police drummer Stuart Copeland and the Chicago Symphony playing the soundtrack to "Ben-Hur," London Philharmonic performing a classical program, the annual Halloween Haunts concert and more.

Oct. 14-Nov. 16
 
Source: Unite Urban Grill

Unite Urban Grill offers a "seasonally inspired, diverse menu" (Time Out Chicago) that puts "upscale twists on old favorites" (Metromix).

Sept. 23, 2014 - Dec. 23, 2014; closed Monday
 
Source: Usagi Ya Sushi

The 2013 Michelin Guide says that the Usagi Ya menu "shines with its unorthodox combinations." Subscribers save more than 50% on this four-course dinner.

Sept. 18, 2014 - Feb. 28, 2015
 
Source: Browntrout

Discover "surprising, inspiring" cuisine that Zagat rates as Excellent (24) at Browntrout. Save on a selection of small plates including a $50 wine credit.

Sept. 18, 2014 - Nov. 30, 2014
 
Source: Mills Entertainment

Everyone knows about the best-selling novel "Fifty Shades of Grey" by E.L. James; now you and your friends can see the "laugh-out-loud funny" (Chicago Reader) stage parody "Spank!"

Oct. 14, 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
 
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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