Best of Chicago

Best of Chicago Flyer: 5412-2 Chicago Theater 3nt Hyatt coach

Best of Chicago

Choice of Broadway Show, Dinner, Hyatt Chicago Magnificent Mile 3-Night Stay with Airfare for 2

Suggested Retail Value: Up to $5,985  Starting Bid: $3,450.00

This Experience Includes:

  • 2 Premium Orchestra tickets to one Broadway show of your choice
  • $200 gift card towards dining at your choice of participating Chicago restaurants
  • 3-night stay in a standard guest room at Hyatt Chicago Magnificent Mile
  • Round-trip coach class airfare for 2 from within the 48 contiguous U.S. to Chicago
  • Winspire Booking & Concierge Service

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 Bank of America Theatre, Oriental Theatre, Cadillac Palace Theatre, the Auditorium Theatre of Roosevelt University and just off the Magnificent Mile, the Broadway Playhouse at Water Tower Place. Current and upcoming productions include First Wives Club, Disney’s Beauty and the Beast,  Joffrey Ballet – New Works, Jersey Boys, Rain: A Tribute to the Beatles, On Your Feet!, Once, Kinky Boots, Pippin, A Gentleman’s Guide to Love & Murder,  Beautiful – The Carole King Musical, Disney’s The Lion King and Gotta Dance. Shows subject to change.

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!

Chicago Casual Dining

Enjoy a total of $200 in gift cards towards dining at your choice of any of these iconic Chicago concepts:

Cafe Ba-Ba-Reeba®, Authentic Spanish cuisine in a lively, vibrant atmosphere

Everest®, Personal French Cuisine

Hub 51®, Modern American Food in a Hip Casual Environment

Joe’s Seafood Prime Steak & Stone Crab®, Tempting selection of aged prime steaks, wide range of jet-fresh seafood

Maggiano’s Little Italy, Authentic Italian restaurant (5 area locations)

Mity Nice Grill®, “1940’s Style Bar & Grill”

Nacional 27® Modern Latin Restaurant, Ceviche Bar, Salsa Club

Pizzeria Via Stato®, Tavern pizzas, as well as small plates and seasonal salads
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

Tru®, Progressive French

Wildfire® Steaks Chops and Seafood

Participating restaurants are subject to change. Gift cards may be used towards food, alcohol, tax, and gratuity.

 Hyatt Chicago Magnificent Mile

Enjoy a 3-night stay in a standard guest room at this Four Diamond hotel nestled in the heart of Michigan Avenue, an area known as The Magnificent Mile. In addition to exceptional shopping, explore the Museum of Contemporary Art, Shedd Aquarium, Soldier Field, Wrigley Field and Navy Pier. Enjoy a walk along the 18 mile Lakefront Trail showcasing vast views of Lake Michigan adjacent to the Chicago skyline. Complimentary WiFi access included.


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 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, 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.