We use cookies to optimise your experience on Travelzoo. By using our website, you are agreeing to allow this. For more information, see our Privacy & Cookie Policy »

  1. Chicago
Deal Cart (0)
Updating Deal Cart
Order Total
Proceed to Payment
Your deal cart is empty. When you add a deal, it will appear here. Updating Deal Cart

Restaurant Deals

$20 -- Chicago Mag Praised Burgers or Breakfast, Reg. $40

$20 -- Chicago Mag Praised Burgers or Breakfast, Reg. $40

Source: Whisk Chicago

Inspired by noted carnivore Ron Swanson, Whisk "mixes burgers and pancakes in a way that would make the Parks and Rec character proud" (Chicago mag).

Oct. 6, 2014 - March 6, 2015; not valid Sundays


Unite Urban Grill: Dinner, Brunch or Drinks, Save 40%

Unite Urban Grill: Dinner, Brunch or Drinks, Save 40%

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


93% (14 ratings)

$45 -- Browntrout: Farm-to-Table Dining for 2 w/$50 in Wine

$45 -- Browntrout: Farm-to-Table Dining for 2 w/$50 in Wine

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


The Garage: Gourmet Tacos or Cooking Classes, Save up to 40%

The Garage: Gourmet Tacos or Cooking Classes, Save up to 40%

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


$19 -- River North: Drinks at 4-Diamond Hotel Bar, 50% Off

$19 -- River North: Drinks at 4-Diamond Hotel Bar, 50% Off

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


93% (41 ratings)

$35 -- Pizzeria UNO: Deep-Dish Cooking Class w/Lunch

$35 -- Pizzeria UNO: Deep-Dish Cooking Class w/Lunch

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


100% (32 ratings)

Randolph Street: 40% Off Alfresco Tapas Dining & Drinks

Randolph Street: 40% Off Alfresco Tapas Dining & Drinks

Source: Nia

This "comfortable tapas spot" in the West Loop offers "a laid back vibe" (Metromix). Subscribers can save over 40% on a selection of tapas and drinks.

Aug. 11, 2014 - Nov. 30, 2014


82% (17 ratings)

W Hotel in the Loop: Brunch for 2 or 4 w/Cocktails, 50% Off

W Hotel in the Loop: Brunch for 2 or 4 w/Cocktails, 50% Off

Source: IPO Restaurant

New executive chef Fernando Coppola's first menu at IPO in the Loop has been unveiled -- subscribers can get a first look at his brunch cuisine for 50% off.

Aug. 2, 2014 - Nov. 2, 2014


83% (84 ratings)

Burgers & Sides in Wrigleyville or Streeterville, Save 50%

Burgers & Sides in Wrigleyville or Streeterville, Save 50%

Source: On The Bun

On The Bun features burgers made from prime and Kobe-style steak, served on pretzel rolls or even waffles. Subscribers can visit and save 50%.

May 1, 2014 - Nov. 1, 2014


81% (43 ratings)

$25 -- West Loop Gem: Italian Dinner for 2, Half Off

$25 -- West Loop Gem: Italian Dinner for 2, Half Off

Source: Ciao! Cafe & Wine Lounge

Time Out Chicago likes the "hearty Italian-American classics" at this West Loop cafe, praised as the "best-kept secret in Chicago" by a recent Travelzoo visitor.

July 15, 2014 - Nov. 15, 2014


85% (130 ratings)

$35 -- Michelin-Recommended Dinner for 2 w/Drinks, Reg. $76

$35 -- Michelin-Recommended Dinner for 2 w/Drinks, Reg. $76

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


93% (124 ratings)

$45 -- Delicious Magnolia Cafe: Dinner for 2, Reg. $83

$45 -- Delicious Magnolia Cafe: Dinner for 2, Reg. $83

Source: Magnolia Cafe

Zagat says the "delicious fare" at Magnolia Cafe "makes for a fun escape"; Travelzoo subscribers can sample three courses for up to 46% off.

July 15, 2014 - Nov. 14, 2014


87% (46 ratings)

$25 -- Wrigleyville: Tapas & Cocktails for 2, Reg. $65

$25 -- Wrigleyville: Tapas & Cocktails for 2, Reg. $65

Source: Raw Bar and Grill

Located in Wrigleyville, this "Check, Please" praised venue offers subscribers a selection of tapas plates and cocktails for up to 62% off.

Aug. 7, 2014 - Nov. 26, 2014


83% (66 ratings)

West Loop: Top-Rated Italian Dinner for 2, Save 40%

West Loop: Top-Rated Italian Dinner for 2, Save 40%

Source: Trattoria Isabella

Metromix likes the "hearty portions" of "must try" appetizers and says "it's tough to choose" between Trattoria Isabella's Sicilian-focused entrees.

Oct. 13, 2014 - Jan. 13, 2015; Sunday-Thursday only


Pazzo's: Italian Dinner for 2-4 Near the Lyric, Save 35%

Pazzo's: Italian Dinner for 2-4 Near the Lyric, Save 35%

Source: Pazzo's @ 101

Dine with a view of the Lyric Opera building at Pazzo's @ 101, a 4-star OpenTable destination. Subscribers can save 35% on dinner.

Oct. 13, 2014 - Jan. 13, 2015; closed Sundays


$99 -- Dozens of Chicago's Best Chefs Cook for You All Night

$99 -- Dozens of Chicago's Best Chefs Cook for You All Night

Source: Meals on Wheels Chicago

SOLD OUT

Bringing together dozens of the city's best chefs, the Meals on Wheels Chicago Celebrity Chef Ball is "always one of the most spectacular" culinary events of the year. (Chicagoist)

Friday, Nov. 7, 2014, 8:30 p.m. - 12:30 a.m.


'Elegant' Alfresco Drinks & Dining, Save up to 55%

'Elegant' Alfresco Drinks & Dining, Save up to 55%

Source: Rivers

SOLD OUT

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

Aug. 20, 2014 - Oct. 10, 2014


89% (36 ratings)

$89 -- Willis Tower: Dinner for 2 at 67th-Floor Private Club

$89 -- Willis Tower: Dinner for 2 at 67th-Floor Private Club

Source: The Metropolitan Club of Chicago

SOLD OUT

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


92% (1122 ratings)

CBS-Praised 'Best French Restaurant' Dinner for 2, Save 40%

CBS-Praised 'Best French Restaurant' Dinner for 2, Save 40%

Source: Cyrano's Farm Kitchen

SOLD OUT

Recently named one of the best French restaurants in the city (CBS Chicago), Cyrano's Farm Kitchen offers subscribers a three-course dinner for two. 

July 25, 2014 - Oct. 25, 2014; closed Sunday-Monday


$25 -- Award-Winning Theory: Brunch & Bloody Marys for 2

$25 -- Award-Winning Theory: Brunch & Bloody Marys for 2

Source: Theory

SOLD OUT

Travelzoo subscribers can save on brunch at this award-winning "modern sports-focused lounge" (Metromix) in River North.

Aug. 9, 2014 - Sept. 21, 2014; Saturday-Sunday only


92% (52 ratings)