Chicago is a city full of iconic attractions, and two must-visit destinations that belong on everyone’s list are Wrigley Field and Skydeck Chicago at Willis Tower. Whether you’re a local looking for a fun weekend activity or a tourist experiencing Chicago for the first time, combining a day at Wrigley Field with a visit to Skydeck offers an unforgettable adventure filled with history, excitement, and breathtaking views.
A Day at Wrigley Field and Wrigleyville
One of the best ways to experience Chicago in the Summer is by catching a game at the historic Wrigley Field, home of the Chicago Cubs. As one of the most iconic ballparks in Major League Baseball, Wrigley Field offers an old-school charm that makes watching a game here truly special.
Wrigley Field Through the Years
Built all the way back in 1914, Wrigley Field is actually Major League Baseball’s second-oldest stadium—the honor of oldest MLB ballfield goes to Boston’s Fenway Park. Nonetheless, many residents consider the field’s distinctive ivy and throwback style an irreplaceable piece of Chicago identity. Here’s a brief look at some key moments in the history of Wrigley since 1914:
- 1914 – Wrigley Field opens as Weeghman Park for Charles Weeghman’s Chicago Whales of the Federal League.
- 1920 – The park is renamed Cubs Park.
- 1921 – Chewing gum magnate William Wrigley Jr. of the Wrigley Company acquires the team.
- 1927 – The park is renamed once again as Wrigley Field, and an upper deck is added.
- 1937 – Bill Veeck, the son of the club president, sees ivy walls at Perry Stadium, Indianapolis—and plants the now-iconic ivy vines against Wrigley’s outfield walls.
- 2020 – Wrigley Field is awarded national landmark status.
- 2021 – Cubs welcome back fans to Wrigley Field after COVID-19 restrictions, with a full-capacity return in June.
- 2022 – The historic Marquee Gate is renamed Budweiser Bleacher Gate as part of a sponsorship deal.
- 2023 – Cubs install state-of-the-art LED lighting, replacing the original lights from 1988 to enhance visibility while maintaining Wrigley’s historic charm.
- 2024 – Wrigley Field hosts its 10th NHL Winter Classic, featuring the Chicago Blackhawks in an outdoor hockey showdown.
- 2025 – The Gallagher Way expansion continues with additional dining, entertainment, and family-friendly attractions, further solidifying Wrigleyville as a year-round destination.
How to Enjoy Wrigley Field & Wrigleyville Before or After the Game
For Families:
- Take a guided tour of Wrigley Field before game time to explore behind-the-scenes areas like the dugout, press box, and ivy-covered outfield wall.
- Visit Gallagher Way, an open-air plaza outside the stadium featuring kid-friendly events, live music, and even a winter ice rink during the colder months.
- If you’re looking for delicious and family-friendly options, grab a bite at Smoke Daddy BBQ or Big Star.
For Locals Looking for a Fun Afternoon:
- Stop by The Cubby Bear or Sluggers for pre-game drinks and live entertainment.
- Explore Murphy’s Bleachers, a local favorite, for great views of Wrigley Field from the rooftop seating.
- Enjoy craft beer and great eats at Lucky Dorr, a hidden gem right next to the stadium.
- Visit Swift & Sons Tavern, located across the street from Wrigley Field
For Tourists Wanting a True Chicago Experience:
- Walk through Wrigleyville, a lively neighborhood filled with sports bars, souvenir shops, and entertainment venues.
- Visit The Chicago Sports Museum for an interactive experience filled with Cubs memorabilia.
- Explore The Music Box Theatre, a historic Chicago landmark that showcases indie and classic films.
After soaking in all the excitement of Wrigley Field and Wrigleyville, head downtown for the next stop on your perfect Chicago day—Skydeck Chicago at Willis Tower.
Experience Skydeck Chicago
A visit to Skydeck Chicago isn’t just about the views—it’s an immersive experience that highlights the best of Chicago’s history, architecture, and skyline. Located on the 103rd floor of Willis Tower, Skydeck is the highest observation deck in the Western Hemisphere and a must-visit attraction.
What to Do at Skydeck Chicago
The Museum:
Come experience Skydeck Chicago by exploring the interactive museum on the lower level of Willis Tower. This newly renovated experience takes you through Chicago’s rich history, from its iconic skyline to its deep-dish pizza culture and sports legacy. Perfect for families, history buffs, and first-time visitors!
The Ledge:
One of the biggest highlights at Skydeck is The Ledge—a series of glass-floor balconies extending 4.3 feet from the building, giving you a heart-pounding, straight-down view from 1,353 feet in the air.
- Great for tourists wanting an unforgettable photo opportunity.
- Families will love the thrill of stepping out over the city.
- Locals can check off a classic Chicago bucket-list experience.
Events at Skydeck:
Looking for something unique? Skydeck hosts private events, including proposals, corporate gatherings, and even sunrise yoga sessions with a view like no other.
Dining at Skydeck:
Before wrapping up your visit, grab a bite at Catalog at Willis Tower, featuring some of Chicago’s top dining options, including:
How to Get from Wrigley Field to Skydeck Chicago
- By Car/Rideshare: A quick 15-20 minute drive south via Lake Shore Drive or I-90.
- By Public Transit: Take the Red Line from Addison Station to Jackson Station and walk a few blocks west to Willis Tower.
- By Bike: Use Divvy bike-sharing stations near Wrigley Field and ride along Chicago’s bike-friendly streets.
Make the Most of Your Chicago Adventure
Pairing a day at Wrigley Field with a visit to Skydeck Chicago is the perfect way to experience the best of Chicago’s sports culture, local flavor, and breathtaking views. Whether you’re enjoying a game, exploring Wrigleyville’s vibrant scene, or standing 1,353 feet above the city at Skydeck, this itinerary offers something for everyone, including family friendly activities.
Plan your visit today and make unforgettable memories in the Windy City!