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10 Awesome Team Outing Ideas in Chicago

Company outings are a key strategy for establishing a solid, interconnected, and mutually supportive workplace culture. That’s why these events should be a major part of every organization’s toolkit. And, if you’re based in Chicago, you’re especially lucky, as there’s a massive number of fun things to do in this city. There’s an abundance of arts and culture to appreciate, delicious food to devour, as well as glorious landscapes and architecture to admire. That said, here’s our list of the 10 most noteworthy team outing ideas in Chicago.

1. A picnic at one of the city’s lush parks

Whether you visit Millennium Park, Lincoln Park, Douglas Park, or any other of the city’s hundreds — that’s right, hundreds — of parks, this is a back-to-basics idea that’s a classic for a reason. There’s nothing better than a delicious spread of picnic classics: potato salad, sandwiches, lemonade, and the like.

Plus, since parks are typically free to visit, this is a low-budget option as well — all you’ll need to pay for is food and perhaps transport, depending where you go. The casual environment will help everyone feel comfortable sharing their thoughts and ideas, as well as help facilitate bonding among coworkers.

There’s also lots of research showing that simply spending time in green spaces is one of the most effective ways to revitalize your body and mind. For these reasons and more, a great picnic is one of our favorite team outing ideas in Chicago.

2. A night or weekend in a literal mansion

If you’ve got more of a budget to spare, your team will surely enjoy spending a day or two at a historic mansion. Consider taking advantage of the ambiance to play a Clue-style murder-mystery game. If you’d prefer, just sit back and enjoy the magnificent environs — or go exploring with your team while developing stronger relationships with your co-workers. Here’s a 1916 French chateau available to rent on Peerspace — it’s absolutely stunning.

3. A fun escape room experience

Escape rooms are immersive puzzles in which participants are trapped in a room and have to work together to figure out how to — you guessed it — escape! Talk about teamwork. This is a great way to help colleagues get comfortable working together to solve problems on the fly.

And what makes escape rooms even more entertaining is that they’re often designed around themes as varied as zombies, the ’90s, spy thrillers, and lots more. We especially recommend The Escape Game, the city’s top-rated escape room on TripAdvisor with thousands of five-star reviews.

4. A team event with Chicago Dine-Around

Chicago Dine-Around is a corporate event planning company that focuses on dining-related team-building and networking experiences. They’ll give you behind-the-scenes access to some of the city’s best restaurants. Co-workers can cook together at an interactive culinary experience or collaborate on one of many team events.

5. A work session in a cool meeting space

If you’d prefer to get down to business — for a collaborative office project — but in a new and invigorating environment, a simple but attractive meeting space is probably the way to go. Peerspace has plenty of options. For example, one guest described this Wicker Park location as a “beautiful and intimate space.” It’s got plenty of natural light, an open kitchen to help you fuel up during breaks, and several different kinds of seating.

6. An indoor skydiving trip

Did you think doing an escape room sounded adventurous? We’ll do you one better. Help your co-workers cross skydiving off their bucket list by having your team outing at iFLY Chicago, Lincoln Park, an indoor skydiving facility that will get everyone’s adrenaline pumping!

7. A dinner in an elegant home

A one-night outing option that will still help to cultivate connections among co-workers is a catered dinner in the nicest home you can find. Here’s our recommendation: this West Loop penthouse with extensive outdoor space. As the sun sets and night falls, guests will enjoy the view of the lit-up skyline as they sip cocktails, eat a delicious meal, and get to know each other with great conversation.

8. A trip to a home outside the city, surrounded by nature

Find a nice short-term rental house or cabin on Peerspace. Aim for a spot right outside of Chicago that’s within reasonable driving distance of the city. As we mentioned in the first item of this list, just being in green spaces is one of the most effective ways to recharge and re-energize. Your whole team can spend a weekend together relaxing, brainstorming, and bonding. You’ll come out of it with a happier and more unified office.

9. A tour of the city

Chicago Detours offers all kinds of private city tours with a wide variety of themes. There’s the Chicago World’s Fair Tour with bars, the Loop Interior Architecture Tour, as well as the Chicago Jazz, Blues, and Beyond Bus Tour, just to name a few. Whichever you choose, these tours are a great opportunity to step outside of the office and into the city. Your team will be guided by a trained and knowledgeable docent, and your colleagues can develop greater rapport among themselves.

10. An urban kayaking excursion

Here’s an unexpected idea: a kayak trip with a private outing planned by Urban Kayaks. It’s sure to help co-workers connect and get to know one another. This is a completely new way to see the city — just imagine looking up at the city’s glorious architecture from your spot on the water. There are two locations to choose from: the Chicago River and Monroe Harbor. In addition to kayaking, paddleboarding is also an option. Either way, your team is sure to have a blast.

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