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

Chicago hotels, entertainment and free events

Deals into Fall
 
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: 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: Puerto Rico Tourism Company

This island-wide sale includes breakfast, room upgrades and beachfront savings up to 55% off.

Through Dec. 19
 
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

Warm up this winter with 6 all-inclusive nights in Cancun during peak season.

Select January-April departures
 
Source: Grand Geneva Resort & Spa

Enjoy a fall foliage or ski trip at this family-friendly resort

Through Jan. 30
 
Source: Jazziz

Travelzoo subscribers can save up to 50% on any of five upcoming concerts, including Jon Secada, Macy Gray and an ABBA tribute band.

Select dates through Nov. 12
 
Source: Ale Harvest Festival

Autumn is a great season for beer: pumpkin beers, brown ales and harvest beers with fresh hops all are released. Taste more than a dozen at the Ale Harvest Fest.

Oct. 11, 2014, 1-5 p.m.
 
Source: Blue Man Group

"Blue Man Group" at Briar Street Theatre in Chicago is now offering Travelzoo subscribers an exclusive deal that saves $20 on all performances through Dec. 24.

Shows through Dec. 24
 
Source: MSG Chicago LLC

"Dr. Seuss' How The Grinch Stole Christmas! The Musical" has been praised as an ideal holiday show for young audiences, with "grand sets and clever stagecraft" according to The New York Times.

Nov. 20, 23, 25, 26
 
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: 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
 
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Travelzoo Tips

Elisabeth Barker — Travel, Entertainment and Local Deal Expert
Elisabeth Barker
Deal Expert, New York
On Saturday, wander the halls of a new-to-you exhibit at no cost. More