Broadway in Chicago

Choice of Broadway Show, Dinner, 2-Night Stay at the Fairmont Chicago, Millennium Park with Airfare for 2

This Experience Includes:

  • 2 Premium Orchestra tickets to one Broadway show of your choice
  • Dinner for 2 at your choice of participating Chicago restaurants
  • 2-night stay in a standard Fairmont room at the Fairmont Chicago, Millennium Park
  • Daily breakfast for 2
  • Round-trip coach class airfare for 2 from within the 48 contiguous U.S. to Chicago, IL

Chicago’s theater scene is one of the seven wonders of this vibrant city. It’s so woven into the urban neighborhoods that it has become part of the fabric of Chicago. Move over, New York, because Chicago’s Broadway scene is giving you a run for your money!

Theater Tickets
Enjoy two Premium Orchestra tickets (first 15 rows center section) to your choice of one of the exciting shows in Chicago’s bustling Downtown Theater District, subject to availability.  Select from a range of musicals and plays on the stages of five of the finest theatres in Chicago’s Loop including the CIBC Theatre, Oriental Theatre, Cadillac Palace Theatre, Auditorium Theatre of Roosevelt University and just off the Magnificent Mile, the Broadway Playhouse at Water Tower Place.

Some current and upcoming productions:  Come From Away, Dear Evan Hansen, Frozen, My Fair Lady, The Office! A Musical Parody, The Simon & Garfunkel Story Shows subject to change and are based on availability.

Chicago Casual Dining
Enjoy a total of $150 in gift cards towards dining at your choice of iconic Chicago concepts including:

  • Bub City® – BBQ, beer, bourbon and the best of country music
  • Cafe Ba-Ba-Reeba® – Authentic Spanish cuisine in a lively, vibrant atmosphere
  • Everest® – Personal French cuisine and unique wine collection
  • Hub 51® –  Modern American food in a hip, casual environment
  • Petterino’s® – Classic Italian, prime steak and fresh seafood
  • Ramen-san™ – Ramen noodle reminiscent of traditional ramen shops in Japan
  • RPM Steak® – Modern chef-driven steakhouse in partnership with Bill and Giuliana Rancic
  • Shaw’s Crab House® – Jazzy, sophisticated, seafood restaurant and a carefree, lively oyster bar
  • Tallboy Taco® – Casual taqueria operating out of Nacional 27

    Participating restaurants are subject to change. Lettuce Entertain You gift cards may be used towards food, alcohol, tax, and gratuity.

Fairmont Chicago, Millennium Park
Enjoy a 2-night stay, including daily breakfast for 2, in a standard Fairmont room at this 4-star hotel.  On cue with the first signs of spring, the Fairmont Chicago, Millennium Park is blooming from a multi-million dollar refresh.  Anchored by 400+ acres of protected park space in the heart of downtown Chicago, the hotel enjoys pristine views of Lake Michigan, Millennium and Grant Parks and the famous Chicago Skyline.

This package includes round-trip coach class service for two from any major metropolitan airport in the 48 contiguous United States to Chicago, IL, subject to availability.

Airfare taxes and a $25 per person processing fee are the responsibility of the purchaser. Blackout dates: Thanksgiving, 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.


Travel must be completed within two years from the date of purchase.  Reservations are subject to availability, and must be booked a minimum of 60 days prior to travel.  Ground transportation is the responsibility of the winner unless otherwise stated.  Certificates cannot be replaced if lost, stolen or destroyed.  Purchases through charity fundraisers are non-refundable and packages cannot be resold.

1 in 100 Entrants
AT UP $5000