Discover Chicago Dining

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Dine at Your Choice of Over 20 Restaurants, 3-Night Stay with Airfare for 2 from Canada (3390-2C)

This Experience Includes:

  • $400 in gift cards towards your choice of participating Chicago restaurants
  • 3-night stay in a standard guest room at a Hyatt, Hilton, Marriott, or comparable hotel
  • Round-trip coach class airfare for 2 from Canada to Chicago, IL
  • Winspire booking & concierge service

The secret is out: as Saveur Magazine reports, "the Windy City is America's new culinary star." And with good reason. Chicago's ever-evolving culinary scene reaches tantalizing new heights every day! While the world takes notice, innovative chefs - many emphasizing foods from America's Heartland - are fusing flavor and excitement in delectable ways. Chicago is such a food lover's paradise that diners face just one dilemma: How to choose from so many delicious options? Match your mood to one of the city's elegant dining spots, charming cafes, intimate bistros, convivial eateries, pizza palaces, or another of the endless alternatives.

Chicago Casual Dining
Enjoy a total of $400 in gift cards to enjoy several meals at your choice of any of these amazing Chicago concepts, and more:

Bub City® - BBQ, beer, bourbon and the best of country music
Cafe Ba-Ba-Reeba® - Authentic Spanish cuisine in a lively, vibrant atmosphere
Ema™ - Mediterranean restaurant showcasing the chef’s lighter California style of cooking
Everest® - Personal French cuisine
Frankie’s Scaloppine® - Neighborhood Italian restaurant
Hub 51® - Modern American food in a hip casual environment
Il Porcellino™ - Rustic everyday Trattoria
Intro Chicago™ - Innovative, casually upscale restaurant introducing up-and-coming talent
Joe's Seafood Prime Steak & Stone Crab® - Tempting selection of aged prime steaks, wide range of jet-fresh seafood
L20® - A modern seafood restaurant
M Burger® - Burgers, fries and shakes
Maggiano's® Little Italy - Authentic Italian restaurant (5 area locations)
Mity Nice Grill® - "1940's Style Bar & Grill"
Mon Ami Gabi® - A classic French bistro
Nacional 27® - Modern Latin restaurant, ceviche bar, Salsa club
Osteria Via Stato® - Rustic, Italian inspired menu in a warm, welcoming atmosphere, 
Oyster Bah™ - Oyster bar and East Coast-inspired seafood
Petterino’s® - Classic Italian, prime steak and fresh seafood
Pizzeria Via Stato® - Tavern pizzas, as well as small plates and seasonal salads
Ramen-san™ - Ramen noodle reminiscent of traditional ramen shops in Japan
Reel Club® - Real fish, real fresh
RPM Steak® - Modern, chef-driven steakhouse in partnership with Bill and Giuliana Rancic
Shaw's Crab House® - Jazzy, sophisticated seafood restaurant and a lively oyster bar
Tru® - Progressive French
Wildfire® Steaks  Chops and Seafood
Wow Bao® - Hot Asian steamed buns

Participating restaurants are subject to change. Dining gift cards never expire and are valid at all participating Lettuce Entertain You restaurants with no blackout dates. Gift cards may be used towards food, alcohol, tax, and gratuity. Dining purchases will be deducted from the cards until the value reaches zero. Any amount not used when paying for your meal stays on your gift card. You can use the remaining balance on your card at your next visit to any Lettuce Entertain You restaurant.

NOTE: Minimum legal drinking age is 21.

Hotel Accommodations
Enjoy a 3-night stay in a standard guest room in hotel accommodations such as the Hyatt, Hilton, Marriott, or comparable.

This package includes round-trip coach class service for two from any major destination* in Canada to Chicago, IL, subject to availability.

*Participating departure destinations in Canada: Calgary, Edmonton, Halifax, Montreal, Ottawa, Quebec City, Regina, Saskatoon, Toronto, Vancouver, and Winnipeg.

Airfare must be booked within one year from the date of purchase. Airfare taxes and a $25 per person processing fee are the responsibility of the purchaser. Blackout dates: Thanksgiving (U.S.), Christmas, and New Year’s weeks.

Business and First Class upgrades are available at the time of booking for an additional fee. Use of frequent flyer miles for upgrades is dependent on specific ticket restrictions as determined by the airline’s frequent flyer program.

Winspire Booking & Concierge Service
Winspire provides a team of seasoned travel professionals who will help you redeem your experience. All travel related details and reservations are handled for every part of your Winspire experience. Operating as a full-service travel agency, Winspire can assist with extra hotel nights, airfare upgrades, and additional guests. This service also provides you with an established network of onsite contacts who can help you book additional experiences, activities and tours.


Must be booked a minimum of 60 days in advance. Reservations are subject to availability. Certificates cannot be replaced if lost, stolen or destroyed. All purchases are non-refundable. Packages cannot be resold. Suggested retail value is calculated using tariff air rates and rack room rates. Ground transportation is not included.

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