A Historic Ballpark And Buzzing Nightlife Put This Trendy Chicago Neighborhood On The Map

Perched on the shores of Lake Michigan, the bustling Midwestern metropolis of Chicago goes by many names. The Windy City, Mud City, Chi-Town, The City of Big Shoulders, and Second City are a few of the most popular. Regardless of which nickname you favor, it's undeniable that Chicago is a city that holds a special place in the hearts of locals and tourists alike. It's almost impossible to think about the Jazz Age without visualizing Chicago in the 1920s. The Great Migration brought an influx of African Americans from the South, and they imbued the city with this culture and music. Industry thrived, the nightlife was lively, and the city began to flourish. Since then, it's only continued to grow, and now it's the third most populated city in the United States.

Throughout the city's ongoing evolution, one thing has remained constant –– a professional baseball team that is adored by locals whether they win or lose. The Chicago Cubs' home stadium, Wrigley Field, has remained an iconic landmark in the city for over a hundred years, but the surrounding neighborhood has recently exploded in popularity.

According to TripAdvisor's Trendcast 2025 report, visiting "nano" neighborhoods is one of the hottest new travel trends. Wrigleyville was listed as one of the most buzz-worthy spots, with page views up 72%. Sports tourism is also on the rise. Chicago is home to multiple neighborhoods that each possess their own unique charms, but Wrigleyville offers something for every type of traveler. Whether you're into sports, nightlife, art, shopping, or history, you'll find plenty to fall in love with on a visit to Wrigleyville.

Wrigleyville is a neighborhood within a neighborhood. It falls within the larger Lakeview neighborhood on the north side of Chicago. If you fly into Chicago, you'll probably arrive at either Chicago Midway Airport or Chicago O'Hare. Both are major international hubs with direct flights to destinations all over the globe. Chicago O'Hare is the larger of the two, but Chicago Midway is a little closer to Wrigleyville.

The beautiful Midwest city has an extensive network of trains that can take you pretty much anywhere you need to go, so renting a car isn't really necessary. If you do decide to rent a vehicle, expect lots of traffic and expensive parking. Car rentals in Chicago cost about $50 per day. The rapid transit system, which is affectionately known as the "L" due to its elevated tracks, is the most convenient way to reach Wrigleyville from either airport without a car. From Chicago O'Hare, it takes about an hour, and from Midway, it takes about 45 minutes. Train tickets from the airport cost about $5.

Once you've reached Wrigleyville, the area is pretty walkable, and there are plenty of public buses, taxis, and rideshares like Uber and Lift that make getting around easy. The rest of the city is just a quick ride away on the "L." A one-day pass with unlimited rides on the "L" costs just $5, so it's convenient and affordable.

You should definitely add a visit to Wrigley Field to your Chicago bucket list. The Major League Baseball season runs from late March through early October, which coincides with Chicago's best weather. The city is quite frigid in the winter, and single-digit temperatures with subzero wind chills are not uncommon. By the time the city thaws, baseball season will be in full swing. If you're in town for a game, you should absolutely go. Nosebleed tickets often go for around $20, so it's a budget-friendly activity that is quintessentially Chicago.

Chicagoans take baseball very seriously. It's a huge part of the city's culture and history. There are actually two major league baseball teams, The Cubs and the White Socks, and they're bitter rivals. The White Socks are the darlings of Chicago's South Side, and fans of The Cubs are traditionally from the Northside. A "crosstown classic," which is when the two teams play one another, is a very exciting time to visit Wrigleyville.

The Chicago Cubs were first established in 1871, making them one of the oldest teams in the country. Their home stadium, Wrigley Field was constructed in 1914, and it's the second oldest ballpark in the country. Even if you aren't able to catch the Cubs in action, it's worth visiting the historic ballpark for a guided tour that lasts around an hour and a half. The cost is $30 per person. When Wrigley Field isn't being used for baseball, it's transformed into a world-class entertainment venue. You can catch some of the world's most famous musicians live and watch the performance from the field or the bleachers.

Baseball is the overarching theme in Wrigleyville, but you'll also find some cute shops tucked away and plenty of places to eat and drink. Stop by Emerald City Coffee for a caffeine boost or detox from the hot dogs and crackerjacks with a nice organic lunch at Uncommon Grounds. As the sun begins to set, Wrigleyville really starts to light up. The Cubby Bear, which is located right by Wrigley Field, is a sports-bar-meets-music-venue that's been a neighborhood institution since it was founded in 1953. It's the best place to party after a Cubs game and an awesome spot to catch live music year-round. The Cubby Bear also serves classic bar food like wings and burgers. Sluggers, Lucky Dorr, and Murphy's Bleachers are a few other fun sports bars worth checking out.

If you're a fan of movies and historic architecture, you'll love the Music Box Theater, which opened in 1929. Its original design has been well-preserved over the decades, and you'll see a variety of independent and foreign films on the lineup. The Mercury Theater, which is just a short walk from Wrigley Field, is a wonderful place to catch a live theatrical performance. The historic building dates back to 1912 and once hosted silent films.

You'll find plenty of great hotels in the neighborhood. For a luxurious boutique option that's steps away from the ballpark, head to Hotel Zachary. The 4-star hotel has suites with views of Wrigley Field. Room prices start at around $300 per night. The Chicago Hotel Collection Wrigleyville is another great choice, with room prices starting at $175.