Where to Spend Your Corporate Holidays in Chicago


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When looking at an upcoming corporate holiday, it’s time to start thinking about how you will spend your time. You probably want your days off to be as enjoyable as possible. It’s time to think twice about staying home. These holidays are an opportunity to get out and do something fun. When you live in or near the Chicago area, you have many things to do near you all the time when getting out and enjoying the Chicago weather. That’s part of the beauty of living in a metropolitan area. When you step outside your home, there’s rarely a dull moment. It’s important to enjoy yourself to the fullest on days off. A fun game, a relaxing retreat, or an educational adventure can help. In this article, we’ll go over some things to do during your next day or days off and where to spend your corporate holidays in Chicago.

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Things to Do Near Me

As a resident of Chicago, recreational activities sometimes just fall into your lap. Other times, you might need help finding something new to do. Maybe you’ve lived in the city for a while and have run through the same old spots one too many times. Perhaps you’re interested in doing something new. A holiday is the perfect time to try something new. If you feel like branching out, look at the areas surrounding the city. You’ll find some of the most exciting spots in the suburbs of Chicago. Plus, most of these places are easily accessible by car, train, or bus. 

This is your reminder that entertainment doesn’t have to stop at the city limits. There are many areas outside of Chicago are worth visiting. Consider these attractions when deciding where to spend your corporate holidays in Chicago:

Oak Park

Oak Park, Illinois, located on the city’s western border, is a quick trip on the train from the heart of Chicago. The suburb happens to be incredibly culturally significant. Legendary writer Ernest Hemingway was born there, and Frank Lloyd Wright once called Oak Park home. Wright is one of the most famous architects of all time. You probably see traces of his work all around you without even knowing it. When you visit Oak Park, you can see Wright’s work in private homes and public properties. Catch a tour of these architectural gems and visit the museum dedicated to his legacy.

Similarly, there is also a Hemingway museum that’s worth taking a look at. Oak Park itself is also worth exploring. The town has year-round festivals corresponding to the seasons, a vintage movie theater, and a bustling downtown district. 


If you’re interested in getting spiritual on your day off, consider visiting Wilmette. This town will have you traveling north alongside the shores of Lake Michigan. Accessible from downtown Chicago by the Purple Line, this area is home to the Bahá’í House of Worship. Not only does the temple boast beautiful architecture and landscaping, but it’s also one of only seven temples of its kind. Located on Lake Michigan, it is the oldest Bahá’í House of Worship. People of all faiths are welcome to visit, pray, and reflect in this beautiful sanctuary. But this isn’t the only attraction that might draw you to Wilmette. The historical museum currently houses exhibits documenting the town’s rich history

Bedford Park

The village of Bedford Park is located in the Midway area, just on the southwestern border of Chicago. This small village is right in the backyard of Chicago Midway International Airport. You may have passed through it on your way to catch a flight. It’s accessible from the Orange Line and is the perfect spot to answer where to spend your corporate holidays in Chicago. While Bedford Park’s population doesn’t even come close to rivaling Chicago’s, it holds many tourist attractions and activities for all family members. When you first arrive in the village’s heart, you can learn all about the Illinois and Michigan Heritage Canal Corridor. 

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Once you’ve taken in this little piece of Illinois history, there’s even more to see. Bring the whole family and explore the commercial district and historical monuments. There are opportunities to bike, kayak, hike, fish, and raft in the area if the summer Chicago weather agrees with you. And while you’re there, don’t forget to check out Wintrust Sports Complex. We’re the premiere entertainment destination in the Midwest for sport event programming, fun games, and other entertainment. Our center offers facilities to host sports tournaments, laser tag, arcade, and e-sports, and much more.

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Fun Games and Other Things to Do Near Me

Now you know where to spend your corporate holiday in Chicago. These areas outside of Chicago have it all: entertainment, art, history, sports, and more. Plus, all of the areas we’ve mentioned have activities that offer a reprieve from the outdoors if need be. Everyone knows that Chicago weather doesn’t mess around. It’s scorching when it’s hot and freezing when it’s cold. If you find yourself in Bedford Park, feel free to come to Wintrust to get yourself out of the heat. You can play fun games in our arcade and e-sports lounge or grab a bite to eat at our Station Grille. There’s something for everyone when you come to Wintrust. And if you’re still wondering where to spend your corporate holiday in Chicago, contact us to start planning your trip.