124 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: Major Airlines on Fly.com

Departs from Chicago, Dallas, NYC & more

September-December
 
Source: Goway Travel

This weeklong getaway to paradise includes roundtrip air and 4-star accommodations

Nov. 12 - Dec. 13; Jan. 15 - March 31
 
Source: Lion World Travel

View the big five up close on a 5-star trip complete with game drives, a helicopter ride and tours.

Select departures, Nov.-Dec. 2014; Jan.-May 2015
 
Source: Studio Within Salon/Spa

Save 50% on an hourlong massage and facial with a blowout at a top-rated Lakeview salon and spa, which earns 4 stars from more than 100 Yelpers.

Aug. 26, 2014 - Feb. 25, 2015
 
Source: The Roots of American Food

Clear your calendar, foodies -- the Roots of American Food Conference returns to Chicago with a once-in-a-lifetime lineup of culinary powerhouses.

Sept. 7-8, 2014
 
Source: The Metropolitan Club of Chicago

Arguably the greatest view from a restaurant in North America, the exclusive Metropolitan Club in the Willis Tower offers subscribers a luxurious dinner for two.

May 26, 2014 - Sept. 30, 2014; closed Sundays
 
Source: The Weathervane Inn

Head to a cozy inn on White Lake in Montague, Mich. -- located three hours from Detroit and Chicago -- with this deal that saves over 46% on current prices.

Nov. 1, 2014 - Dec. 28, 2014
 
Source: Rivers

Located along the Chicago River, the appropriately-named Rivers is "elegant" with "sleek contemporary appeal" (Metromix).

Aug. 20, 2014 - Oct. 10, 2014
 
Source: Kohl Children's Museum

Kohl Children's Museum "raises 'let's pretend' to an art form" (Metromix); in 2011 Parents Magazine named it one of the best children's museums in America.

Aug. 18, 2014 - Nov. 21, 2014
 
Source: Cici Nails

Harper's Bazaar says autumn nail trends include deep reds, grays and metallics. Subscribers can prepare their digits for fall and save half off.

Aug. 19, 2014 - Feb. 18, 2015
 
Source: Aroma Workshop

Midwest Living says these Signature Scent classes, where attendees create their own personal perfume, are a great way to "tap your creative instincts."

Aug. 15, 2014 - Dec. 31, 2014
 
Source: Pizzeria UNO

Pizzeria UNO is where Chicago's iconic deep-dish pizza was created over 70 years ago. With this exclusive offer, subscribers can learn to craft their own.

Aug. 20, 2014 - Dec. 30, 2014; Tuesday-Saturday mornings
 
Source: UNO Pizzeria & Grill

After inventing deep-dish pizza over 70 years ago, UNO Pizzeria & Grill brought the iconic Chicago recipe nationwide. Now subscribers can craft their own.

Aug. 20, 2014 - Dec. 30, 2014; Tuesday-Sunday mornings
 
Source: UNO Pizzeria & Grill

After inventing deep-dish pizza over 70 years ago, UNO Pizzeria & Grill brought the iconic Chicago recipe nationwide. Now subscribers can craft their own.

Aug. 20, 2014 - Dec. 30, 2014; Tuesday-Sunday mornings
 
Source: UNO Pizzeria & Grill

After inventing deep-dish pizza over 70 years ago, UNO Pizzeria & Grill brought the iconic Chicago recipe nationwide. Now subscribers can craft their own.

Aug. 20, 2014 - Dec. 30, 2014; Tuesday-Sunday mornings
 
Source: UNO Pizzeria & Grill

After inventing deep-dish pizza over 70 years ago, UNO Pizzeria & Grill brought the iconic Chicago recipe nationwide. Now subscribers can craft their own.

Aug. 20, 2014 - Dec. 30, 2014; Tuesday-Sunday mornings
 
Source: Live Nation

The bands will perform from their catalog of hits, including "If You Leave Me Now" (Chicago) and "Can't Fight This Feeling" (REO Speedwagon).

Sunday, Aug. 31 at 7:30 p.m.
 
Source: Hana Lounge at Westin Chicago River North

This "calm, soothingly lit refuge" (Examiner.com) in River North opens its doors to Travelzoo subscribers for drinks and apps for more than 50% off.

Aug. 12, 2014 - Nov. 12, 2014
 
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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