1 deal from our Canadian site*
* Taxes and fees may be additional.
Travel into May
Major Airlines on Fly.com
 
54 deals from our U.S. site*
* Taxes and fees may be additional.

Deals are priced in U.S. dollars and are sourced by our U.S. Deal Experts. Airfare and air-inclusive vacation or cruise pricing includes taxes; hotel, entertainment, car rental, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

Source: Hotel Allegro Chicago

Located in the theater district next to the Cadillac Palace Theater and a short walk to Millennium Park and Magnificent Mile.

Select dates through April 26
 
Source: deca Restaurant + Bar at the Ritz-Carlton Chicago

Members can savor three courses each at the Ritz-Carlton's deca Restaurant + Bar, ranked "very good to excellent" (23) across the board by Zagat.

Through May 19, 2015
 
Source: Virgin America

Snag discounted fares on Conde Nast Traveler's 'Best U.S. Airline'

April 7 - June 10
 
Source: Virgin America

Enjoy extra legroom, priority boarding and seating, one free checked bag, free food and drinks in Main Cabin Select.

April 7 - June 10
 
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.

March 1-5; April 1-5; Other dates from $208
 
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 members a luxe dinner for two.

Through March 31, 2015; closed Sundays
 
Source: Level Two at the Hyatt Chicago Magnificent Mile

Start a weekend downtown trip off right -- members can save more than 40% on brunch with cocktails at Level Two, located at the Hyatt Chicago Magnificent Mile.

Through April 26, 2015; Saturday-Sunday only
 
Source: Randolph Street Market

With dozens of vendors offering antiques, clothing, global goods and gourmet foods, Randolph Street Market is one of the nation's top shopping destinations.

Select weekends throughout 2014-15
 
Source: Pizzeria UNO

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

Through March 31, 2015; Tuesday-Saturday mornings
 
Source: Chuck's: A Kerry Simon Kitchen

With a new menu from celebrity chef Kerry Simon and his brother, executive chef Scott Simon, members can save 40% on a downtown dinner for two.

Through June 8, 2015
 
Source: Tiffani Kim Institute

Members can save nearly 55% on their choice of massage and facial at the Tiffani Kim Institute, a three-story urban River North spa escape.

Through June 26, 2015
 
Source: Carson's Prime Steaks Famous Barbecue

Recently named one of the best barbecue restaurants in America by OpenTable, Carson's offers members more than 30% off dinner and drinks for two.

Through April 30, 2015
 
Source: Meli Cafe

Praised on WTTW's "Check, Please!" for "a warm, welcoming atmosphere" where "attention is paid to every detail," Meli Cafe offers members up to 50% off.

Through March 23, 2015
 
Source: The Mid-America Club

With bird's-eye views of Navy Pier and Lake Michigan, the members-only Mid-America Club opens to members for dinner 1,000 feet above Chicago.

Through March 28, 2015; Wednesday-Saturday only
 
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: The Spa at The Carlton Club

Unwind at one of the world's best hotels (Conde Nast Traveler) with this exclusive invitation to the spa at The Carlton Club in the Ritz-Carlton Hotel.

Through May 19, 2015; Sunday-Friday
 
Source: iO Chicago Theater

With former cast members like Tina Fey, Amy Poehler and Seth Meyers, iO Chicago features tomorrow's famous comedians performing today.

Through March 31, 2015
 
Source: Cook Au Vin

Get ready to knead, toss and mix your way to a better baguette. Members can learn to make some of the city's best bread with a class from Cook au Vin.

Through July 31, 2015
 
Source: Oceanique

Evanston's Oceanique is a "fine-dining standby" with "haute cuisine moves" at a "perennially popular" spot (Chicago magazine).

Through May 13, 2015; closed Sundays
 
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Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
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