A Baseball Fan’s Dream Weekend Away in Chicago: Where to Go and What to Do

There aren’t many iconic destinations that universally appeal to fans of baseball than the Windy City – home to legendary MLB teams, the Chicago Cubs and the Chicago White Sox. Given that the best time to visit Chicago is during the baseball season, we’ve created a magnificent guide for a baseball-fueled weekend away to Chi-Town.

Whether you’re visiting the historic baseball venues themselves or watching the Crosstown Classic baseball game from the Wrigley Rooftops, a trip to Chicago always makes for the perfect family-friendly weekend away or a fun vacation with friends.

See the Sights and Catch a Cubs Game at Wrigley Field

First up, where better to start our baseball pilgrimage than world-famous Wrigley Field, which has been home to the Chicago Cubs since 1914. Here, you can wander around the outside of this remarkable ivy-covered stadium and take photos next to the statues of Cubs legends Ernie Banks, Ron Santo, and Billy Williams.

However, nothing beats watching a game at Wrigley Field, so check the Chicago Cubs baseball schedule if you’re visiting during the MLB season to watch the live action unfold. Whether you choose to sit behind home plate or join the Cubs Nation and the Bleacher Bums sitting in the Wrigley Field bleachers, it always makes for a superb way to watch the ballgame.

Outside of Cubs gamedays, daily tours are also available to take you around Wrigley Field, which allows baseball fans to see behind the scenes and take pictures from the dugout, press box, and even its famous stadium bleachers.

Beyond the Ballpark – What to Visit in Chicago as a Baseball Fan

Another top place to visit with a baseball-oriented theme is the must-see Chicago Sports Museum, which can be found on the Magnificent Mile at the Water Tower Place Mall. Not only does this amazing museum commemorate both MLB’s Cubs and White Sox’s multiple World Series victories, but it also honors the city’s other championship-winning sides, including the NBA’s Bulls, NFL’s Bears, and NHL’s Blackhawks.

Another fantastic venue to witness Chicago’s passionate love affair with baseball is to head down to the Chicago History Museum in Lincoln Park. Here, frequent exhibits allow visitors to dive deeper into the history of baseball in the Windy City, its hometown heroes, and images of all of the Cubs and White Sox World Series wins over the years.

Action-Packed Dining and A Perfect Night’s Sleep in Chicago

For any baseball superfan, the best time to visit Chicago has to be during the baseball season, but if you can’t make it to a game, then you should head down to the incredible Harry Caray’s Restaurant & Museum called the 7th Inning Stretch at Water Tower Place. While the food is always outstanding, it’s also a brilliant location to check out the interactive baseball exhibits and memorabilia, and even watch a ballgame on the big screens while you eat.

With its rich baseball history, whenever you come to Chicago, if you love the game, then you will never leave disappointed, and be sure to top off the dream weekend escape to the Windy City by booking your stay at the stunning Best Western Plus Hawthorne Terrace Hotel on N Broadway Avenue, Chicago, Illinois.

Watch the Crosstown Classic: Cubs vs White Sox

Without a shadow of a doubt, the best time to visit Chicago is to attend the Windy City Showdown, the biggest games on every Chicagoan’s calendar each year – ideal if you love a good rivalry.

Despite the Cubs playing in the National League (NL) and their crosstown neighbors, the White Sox playing in the American League (AL), the two teams still play each other several times every baseball season. Games are played at both Wrigley Field and the White Sox’s Guaranteed Rate Field on the South Side of Chicago, which always thrills spectators every time the White Sox vs Cubs go head-to-head.

After the ballgame, be sure to take some Cubs memorabilia home with you as a memento of your baseball-themed weekend away in Chicago. Stopping off at the Cubs Team Store next door, you can buy a Chicago Cubs baseball cap and matching jersey or even a Cubs jacket to wear on your trip home.