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

Hotels, shows and attractions are discounted during a busy winter season

Deals into March
 
Source: W Chicago City Center Hotel

Centered amongst Chicago's lively cultural attractions, the stylish W Chicago City Center has discounted rates by 35%.

Select dates through April
 
Source: Hotel Rush

Set in a prime location near the city’s best restaurants, iconic landmarks and top shopping.

Travel Jan. 4 - March 31
93% (15 ratings)
 
Source: Wyndham Grand Chicago Riverfront

Fresh off a multimillion-dollar redesign, receive an automatic room upgrade for stays into spring.

Options into April
95% (111 ratings)
 
Source: Millennium Knickerbocker Hotel

Use the credit to try more than 50 types of martinis at the hotel bar

Through March 5; +$10 March 6 - April 9
 
Source: Travel Discounters

See Egypt in style -- stay in a 5-star hotel and cruise along the Nile on a 5-star cruise ship

Weekly departures through December 2015
 
Source: CheapCaribbean.com

Kick back on one of the best beaches in Jamaica with this all-inclusive special; upgrades to the Grand Palladium Lady Hamilton are also on sale

Select departures February-July
 
Source: Apple Vacations

Head to Punta Cana during peak season with this weeklong, all-inclusive vacation

Select departures, January-March
 
Source: Online Vacation Center

Sail aboard Oceania Cruises -- voted a Gold List cruise line by the readers of Conde Nast Traveler.

March 15, 25; +$1500 Feb. 28
 
Source: Travelzoo

Nab sales at the city's top attractions while taking advantage of thinner crowds and shorter lines.

Through March
 
Source: The James Chicago

Select dates in February
100% (4 ratings)
 
Source: Great Value Vacations

With the freedom of a rental car, travelers can tailor this spring sojourn to suit their interests.

Select April-May dates; more dates discounted
 
Source: Lion World Travel

Stay at award-winning hotels, with included perks like massages and helicopter rides.

Select April-December departures
 
Source: Joffrey Ballet

This winter, Travelzoo members can save up to 40% on tickets to The Joffrey Ballet's contemporary program "Unique Voices," including a Valentine's Day matinee. The show is a Time Out Chicago Critics' Pick.

Jan. 23, 2015 - Feb. 23, 2015
 
Source: City Theatre

This deal saves more than 35% on tickets to the "laugh-out-loud funny" stage parody (Chicago Reader).

Jan. 21, 2015 - Feb. 5, 2015
 
Source: Yamato Foot Massage & Bar

Conveniently located in River North near shopping and dining, Yamato Foot Massage & Bar earns 4.5 star reviews from dozens of Yelp visitors.

Through April 21, 2015
 
Source: Table, Donkey and Stick

Members can reserve a seat at the chef's counter at the Michelin-praised Table, Donkey and Stick for a five-course tasting menu and a drink for over 35% off.

Through April 30, 2015; blackout dates apply
 
Source: Allied Live Chicago Office

Music from Elvis Presley, Johnny Cash, Jerry Lee Lewis and Carl Perkins comes to life in "Million Dollar Quartet," now a staple at Chicago's Apollo Theater. Travelzoo members save up to $17.50 per ticket on winter performances with this exclusive offer.

Jan. 14, 2015 - Feb. 25, 2015
 
Source: Grapes to Bottles

Sample dozens of different wines at your choice of events at the Dana Hotel's Freestyle Food + Drink, hosted by the Grapes to Bottles team.

Select dates through April 18, 2015
 
Source: Mills Entertainment

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

Tuesday, Jan. 27 at 7:30 p.m.
 
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Travelzoo Tips

Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
Several hotel chains, including Hilton and Choice Hotels, offer discounts for active More