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Take Me Out to the Ballgame

Take Me Out to the Ballgame: Choose Your Experience


Choose either Boston, Chicago or Spring Training in Scottsdale:

The love of baseball transcends generations, weaving a rich tapestry of memories, tradition, and passion. For many, it begins in childhood, playing catch in the backyard or attending a first game, mesmerized by the sights and sounds of the ballpark. Whether it’s the thrill of a walk-off home run, the tension of a perfect game in progress, or the camaraderie shared among fans, baseball offers an enduring, heartfelt connection to the cherished pastime.

Boston Red Sox, Green Monster

This Experience for 2 Includes: Boston

  • 3-night stay at the Fairmont Copley Plaza
  • Daily breakfast
  • Tickets for 2 atop the Green Monster
  • 2 hour guided walking tour of Boston
  • Winspire concierge & booking service

The Green Monster is one of the most iconic features in baseball. Standing at 37-foot-2 inch tall, this massive green left-field wall at Fenway Park has been a distinctive challenge for hitters since it was built in 1912. It embodies the unique character of Boston and adds to the allure and history of the Boston Red Sox, creating unforgettable moments for players and fans alike.

The Fairmont Copley Plaza

Enjoy a 3-night stay in a standard room including daily breakfast for two at The Fairmont Copley Plaza. This luxury hotel has been a symbol of the city’s rich history and elegance since its prestigious opening in 1912. Together with Trinity Church and the Boston Public Library, this landmark hotel is one of the architectural jewels of Copley Square. To celebrate its centennial anniversary, the hotel has renovated the guest rooms and added a 3,000-square-foot rooftop health club. Centrally located in Boston’s historic Back Bay, The Fairmont Copley Plaza sits steps away from historic Beacon Hill and the Freedom Trail.

The Green Monster

Enjoy 2 tickets to a Boston Red Sox, regular season home game. Green Monster seating or general admission will vary at the time of purchase.

Guided Tour

Journey back to the early years of American history with this guided walking tour of Boston’s most renowned Freedom Trail and its most iconic landmarks. A professional guide accompanies you, providing insightful context along the way.

Blackout Dates: Major US Holidays. The package is available during the regular baseball season.

Chicago Cubs, Wrigley Rooftop

 This Experience for 2 Includes: Chicago

  • 4-night stay at the Talbott Hotel
  • Tickets for 2 at Wrigley Rooftops
  • Sunset Chicago River Tour
  • $150 dining gift card
  • Winspire concierge & booking service

Wrigley Field, nestled in the heart of Chicago’s North Side, is one of the most iconic and historic baseball stadiums in the United States. Home to the Chicago Cubs since 1916, Wrigley Field is renowned for its ivy-covered brick outfield walls, the classic red marquee over the main entrance, and its hand-turned scoreboard that harkens back to an earlier era of baseball.

The Talbott Hotel, Chicago

Enjoy a 4-night stay in a standard room. Located in the heart of Chicago’s Gold Coast and an easy walk to many of the city’s most popular destinations, including The Magnificent Mile, Oak Street Beach, and 360 CHICAGO observation deck in the iconic John Hancock Building. The Red Line is just steps away to take you to Wrigley Field, Navy Pier, or Chicago Riverwalk. The Talbott offers an intimate experience & personalized service, featuring 178 elegant guestrooms, including 40 suites. Guests are offered a variety of amenities and perks, including Complimentary bottled water upon arrival, in-room coffee by Tayst, wi-fi throughout the hotel, and a fitness center open 24/7 featuring a peloton bike and Flowater purified refill station. 

Wrigley Rooftop

Experience the excitement of a Cubs game from a unique vantage point with a visit to the Wrigley Rooftops. Located on the rooftops of the buildings surrounding Wrigley Field, these premier venues offer a one-of-a-kind way to enjoy America’s favorite pastime while taking in the breathtaking views of the historic ballpark.

Just pick the game and everything else will be arranged! Your rooftop admission provides your seats, beverages (beer, wines and soft drinks) and entrees, side dishes, and desserts with a large and varied menu of iconic Chicago fare!

Valid for the Chicago Cubs regular season games, subject to availability. Excludes Opening Day and may exclude other premium series.

Sunset Chicago River Tour

Experience the magic of a Sunset Chicago River Tour, where the city’s stunning architecture and vibrant skyline come alive as the sun sets. This enchanting cruise offers a unique perspective on Chicago’s iconic buildings, bathed in the golden hues of twilight.

Chicago Casual Dining

Enjoy a total of $150 in Lettuce Entertain You Gift Cards to be used 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

Mon Ami Gabi® – Classic French Bistro tucked away in Lincoln Park

Aba® – Hib, a Mediterranean restaurant in Chicago’s historic Fulton Market district

Ramen-san™ – Ramen noodles reminiscent of traditional ramen shops in Japan

Shaw’s Crab House® – Jazzy, sophisticated seafood restaurant, and a carefree, lively oyster bar

Tallboy Taco® – Casual taqueria oin the heart of Streeterville

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

Blackout Dates: Major US Holidays. The package is available during the regular baseball season.

Spring Training

This Experience for 2 Includes: Scottsdale

  • 3-night stay at the Fairmont Scottsdale Princess
  • Tickets for 2, to one spring training game (see teams below)
  • $250 Fairmont gift card (spa, golf, dining)
  • Winspire booking & concierge service


Baseball spring training is an annual tradition that marks the joyful prelude to the Major League Baseball season. This period allows players to refine their skills and build team chemistry. For the fans, spring training offers a more intimate and relaxed atmosphere to watch games, interact with players, and enjoy the sunny weather. With its mix of hopeful rookies and seasoned veterans, spring training is a time of optimism and excitement, setting the stage for the thrilling baseball season ahead.


Fairmont Scottsdale Princess

Enjoy a 3-night stay in a standard Fairmont room including daily breakfast for two at this AAA 5-Diamond resort.  Amenities include four top-ranked Arizona restaurants, six sparkling pools with two water slides, two Jacuzzis, fitness center and Kid’s Club programs.

Receive $250 in Fairmont gift cards that can be used towards golf at TPC Scottsdale and/or spa treatments at the Fairmont Well & Being Spa.

Spring Training

Your choice of one major league spring training game for 2. Teams: Los Angeles Dodgers, San Diego Padres, Texas Rangers, Cleveland Guardians, Kansas City Royals, Anaheim Angels, Milwaukee Brewers, San Francisco Giants, Oakland A’s, Arizona Diamondbacks, Colorado Rockies or Chicago White Sox. If the team relocates, you have the option to select a different team to see play.

Blackout Dates: Major US Holidays. The package is available during spring training season.

Package Redemption

Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.

Booking & Concierge Services

Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.

Additional Information

Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.

Blackout Dates

Blackout Dates: Major US Holidays. The package is available during regular baseball season or spring training season.