Millions of travelers visit Chicago, a city of neighborhoods, each year thanks to its iconic attractions. Think bold architecture flanking a river, a massive lake fringed by a pedestrian-friendly trail and sandy beaches, world-class museums and theater, and landmarks like the Navy Pier, Millennium Park, and the Magnificent Mile.

According to the 2025 Tripadvisor Trendcast, travelers are seeking out ways to celebrate personal milestones, playful and immersive opportunities, multi-generational activities, and fun sporting events. Delving deeper into “nano neighborhoods” for more authentic experiences is also increasingly more important for merrymakers and vacationers. “Travelers are slowing down and taking in one neighborhood at a time. Overtourism and a hunger to have real, authentic experiences are driving us to zoom in on single neighborhoods (even streets!) to find the stuff you can’t get in the guidebooks,” wrote Tripadvisor in its report.

In 2024, Chicago’s Wrigleyville spiked engagement on Tripadvisor’s neighborhood attraction pages by a whopping 72 percent.

Wrigleyville is a dynamic neighborhood. It’s home to the Chicago Cubs and Wrigley Field, the second oldest Major League Baseball Park in the U.S.; the first being Fenway Park in Boston. It’s also where you can eat your weight in deep-dish pizza and Chicago-style hot dogs, revel in the nightlife, and listen to live music. Here’s how to plan your visit.

Rub elbows with locals in a classic sports bar.

The sports bars and pubs around Wrigley Field are legendary. Imbibe pre- or post-game at Sluggers, full of memorabilia, batting cages, and arcade games. Or hop over to Lucky Dorr, which is packed on game days and offers tasty craft beer. There’s also Murphy’s Bleachers, which is located so close to the field that you can hear the baseball action, and The Cubby Bear Chicago, a hot spot with live music.

Eat cheap or indulge in inventive dining.

From happy hour cocktails, beer, and wine to plenty of delicious noshes, Mordecai serves up American-style dishes. Located directly across from Wrigley Field, this is the spot to celebrate with friends and family whether there’s a game or not.

For a view of Wrigley Field’s famous red marquee hanging over the main entrance, book a booth by the window at Swift & Sons Tavern and order a half dozen oysters. For tacos, there’s no better place to go in Wrigleyville than Big Star and indulge in odoriferous barbeque, or to pick up signature sauces, hit up Smoke Daddy.

Penny’s Noodle Shop, a cozy and casual neighborhood favorite located in the curve of the Chicago “L” train, is a keen choice for Thai-style noodles and rice dishes. The Windy City is known for its deep-dish pizza, and there’s always a debate about who serves the best pies. That said, in Wrigleyville, D’Agostino’s Pizza and Pub is a solid choice. An added plus: the Dog Menu is adorable.

Go to a Cubs game.

Seeing the Chicago Cubs play, along with an incredibly loyal fan base, is an inimitable experience. The stadium, built in 1914, sits in the middle of a mostly residential neighborhood and features an ivy-covered brick outfield wall and an immense wooden scoreboard that has someone inside turning the numbers by hand. Barking, “Hot dog here!” at the vendors roaming the aisles is a fun treat. Baseball fans can book a ballpark tour for a more in-depth behind-the-scenes experience.

Stay the night with a view of Wrigley Field.

Hotel Zachary at Gallagher Way is a top-notch stay, no matter what time of year you visit Wrigleyville. Not only are the rooms and public spaces gorgeous and well-designed, but you’ll also be located directly across from the ballpark and all of the year-round activities and events at Gallagher Way like movie screenings, live music, fitness classes, open-air farmers’ markets in the warmer months and ice skating and holiday-themed activities in the winter season.