Best Places to Go During Corporate Holidays in Chicago


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A day off work is a luxury, but sometimes it feels almost impossible to figure out how to spend it. You might be so caught up in a routine that you can’t figure out how to relax and have fun. Winter holidays typically involve set traditions. But during the summertime, you have more flexibility to choose your holiday activities in Chicago. When the weather is warm, it’s a great time to go out and see the sights. This is especially true when you live in a city like Chicago. 

The beauty of living in Chicago is that you always have things going on around you. There’s never a dull moment in the Windy City. During your next extended period off, you should make the most of your time. The instinct to shut yourself away at home might be enticing. However, you’re ultimately missing out on everything the city offers you. In this article, we’ll go over some of the best things to do in Chicago at the current moment. Read along for your official guide when it comes to places to go during corporate holidays in Chicago.

friends having drinks

Events Near Me

There are tons of activities and things to do in Chicago year-round when you’re searching for “events near me.” Attending unique events is a huge reason to live in the city. People come into the city to attend these kinds of events. Here is a short list of events happening this summer: 

Live on the Lake Series

This summer concert series kicks off during Memorial Day weekend at Chicago’s Navy Pier. Here, you can catch free performances each weekend from some of Chicago’s best bands, plus other local and national acts. 

4th of July Fireworks

Another activity in Chicago to keep an eye out for is the firework show on Lake Michigan. You can choose to watch from land, book a fireworks kayak tour, or cruise to see the view from the water. This is also a Navy Pier activity that attracts many people. 

The 4th on 53rd

The 4th on 53rd is the main Independence Day event in the city. It’s a free festival and parade along 53rd Street, which ends in a community picnic at Nichols Park. This is one of the most popular annual events in Chicago and typically draws out 10,000 attendees. 

summer fireworks

Things to Do in Chicago

If you’re looking for more laid-back places to go during corporate holidays in Chicago, we have you covered. Some people aren’t big on parades or large crowds, which is understandable. You can still have fun attending less crowded “events near me” or simply engaging in more informal activities in Chicago. Plus, there’s always a delicious restaurant to eat at, a museum to visit, or a show to see. A day trip is a less intense option when looking for places to go during corporate holidays in Chicago. Your day off is the perfect time to try out new experiences. Maybe you’ve exhausted all your interests in the city. There are plenty of places just outside of Chicago’s borders worth exploring. Plus, many of these places are entirely accessible by car, train, or bus. You wouldn’t believe some of the areas you can get to in as little as half an hour from downtown Chicago. 

Oak Park, IL

This suburb is located on the city’s western border and happens to be the home of two significant American icons: Ernest Hemingway and Frank Lloyd Wright. Hemingway was born in the town and, as many know, went on to become one of the most legendary American writers. Wright was one of the most famous American architects of the 20th Century and established a studio in Oak Park. This town is a quick trip on the train from the heart of Chicago. Around town, you can see Frank Lloyd Wright’s work on both public and private properties. Plus, both Hemingway and Wright have museums dedicated to their respective legacies. Oak Park also has year-round festivals that correspond with the seasons, a vintage movie theater, and a bustling downtown district. 

Bedford Park

The village of Bedford Park is just a 30-minute train ride from downtown Chicago. Located right in the backyard of Midway Airport, there’s a lot to do and see here. Whether you’re on your own or planning an outing with the family, Bedford Park has something for everyone. If the summer weather agrees with you, there are opportunities to bike, kayak, hike, fish, and raft. To get a reprieve from the heat, we suggest visiting Wintrust Sports Complex. Our facility is the center for sports tourism in the Midwest. Plus, there’s plenty of entertainment to go around. From sporting events to gaming opportunities to private events and parties, we’ve got it all. Gamers can check out our e-sports lounge and redemption arcade, while sports enthusiasts can catch a tournament or game. 

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Activities in Chicago for Everyone

It’s essential to take advantage of your day off. The summer is the best time to get out of the house and launch yourself into the action. And one of the best places to go during corporate holidays in Chicago is Wintrust Sports Complex. We have unlimited options for entertainment and amusement, with thousands of games to play right at your fingertips. Plus, we have a full-service kitchen and lounge to retire to when you need to refuel. When you spend your holiday with us, we guarantee you’ll have a blast.