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9 Cool Retreat Activities in Chicago to Bond Your Team

Chicago has long served as a cultural hub of diverse activities and employment opportunities in the Midwest. From Fortune 500 companies to innovative startups, Chicago’s business district draws employees from industries located all over the world. Whether you’re planning icebreaker activities for a huge workforce or a small weekend getaway for an executive team, there’s something for everyone on this list. These nine incredible retreat activities in Chicago are a good place to start. In addition, you can always browse Peerspace listings for more venues and retreat ideas all over the Chicago area and beyond.

1. Enjoy an interactive culinary experience with Chicago Dine Around

Cooking classes or competitions are a great option for corporate retreats, as they get your team working together and enjoying the results of their hard work. Chicago Dine Around offers a range of culinary experiences for corporate teams, including a progressive dining tour that will take your team to a different restaurant for each course, giving them the chance to intermingle and switch tables at each venue. The tour lasts around three hours and can accommodate up to 560 people.

Other activities include an architectural dining tour, which includes a cruise along the Chicago River, as well as interactive workshops that will teach your team how to make deep-dish pizza, mixed drinks, or authentic Italian cuisine. These activities are great for groups of up to 250 people.

2. Book an unforgettable venue on Peerspace

If you want to design your own retreat activities in Chicago from the ground up, then you won’t have to look any further than Peerspace, which offers location rentals from local hosts. The hosts can also help you arrange for catering options and equipment rentals. Choose from options like a multipurpose coworking space complete with an indoor climbing wall to an art and mindfulness space in Irving Park. Many locations have options for A/V rentals and other gear, so you can include presentations, corporate headshots, and other on-site activities as part of your retreat.

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3. Learn acrobatics at Trapeze School New York (TSNY) in Chicago

If trust falls are a little tame for your team, then why not book a trapeze workshop with TSNY Chicago? Their corporate workshops are specifically designed to build trust and team spirit within your group. You’ll learn how to support each other while taking risks and pushing past your comfort zone in a safe environment with trained instructors.

Workshops take place at their studio on Lake Michigan, and can include trapeze, trampoline, and other aerial skills, such as silks and hoops. They’re suitable for people of any experience level. Also available are lower-to-the-ground acts, such as juggling, tight rope, and stilts.

4. Make your own beer with Brew & Grow

For a hands-on activity that includes food and refreshments, book a beer-making workshop with Brew & Grow. Their team will provide all of the gear you’ll need to learn about the brewing process. Best of all, you’ll get to sample a few beers along the way. Their packages can be customized to suit your budget and time constraints. Your team can participate in the activity and interact with each other throughout the workshop. This is one of the most fun retreat activities in Chicago to end the day!

5. Climb together at Brooklyn Boulders

Combine your retreat with a climbing workshop at Brooklyn Boulders, wherein your group can work together both on and off the climbing wall. The crew at Brooklyn Boulders will teach you how to boulder and auto-belay, as well as guide you through exercises to foster communication and problem solving. Choose from a variety of activities to challenge and energize your team.

Plus, Brooklyn Boulders has several additional spaces available to rent on Peerspace, so you can make this an all-in-one retreat location. You’ll have access to meeting rooms, coworking spaces, showers, and yoga and meditation areas all in the same centrally located facility.

6. Host a trivia event with the Game Show Gurus

Bring out your inner Jeopardy! champion with a custom retreat activity designed by the Game Show Gurus. Use trivia questions to build team spirit or educate your employees about a new product launch or workplace protocols. The team at Game Show Gurus will bring the show to you, with lights, props, stages, drapes, and even a tent for outdoor venues.

Game shows are a fun way to encourage participation while giving shy employees a chance to get involved, too. Include some prizes to demonstrate employee appreciation.

7. Work on a volunteer project with Chicago Cares

Use your retreat as an opportunity to demonstrate corporate social responsibility by partnering with an organization like Chicago Cares. With a variety of volunteer options available, you can put your company values to work with hands-on projects that will make a visible difference in your community. Whether you prefer to plant trees or organize a neighborhood cleanup project, the team at Chicago Cares can help you find the perfect option for groups of any size.

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8. Stay overnight at the Loyola University Retreat & Ecology Center

Get away from it all at the Loyola University Retreat & Ecology Center, which is just around an hour’s drive from downtown Chicago. With hotel and dorm-style accommodations and a variety of meeting spaces available, the spot offers everything you need for a weekend retreat outside of the city. This venue also offers team-building workshops, including a ropes and zip line course, as well as culinary workshops that demonstrate sustainable cooking techniques.

Plus, you’ll have 98 acres of outdoor space available for guided and solo hikes, bird-watching, and more. This is an all-inclusive retreat activity in Chicago for groups of up to 200 people.

9. Relax during a meditation retreat with Chill Chicago

Bring mindfulness into the workplace with Chill Chicago, which offers meditation retreats for corporate teams. They’ll help you design a customized program to improve your company’s productivity and focus. Bring them to your office for regular mindfulness sessions, or design an all-day workshop to reduce stress and foster creativity.

Whether your team has meditated before or are totally new to the practice, Chill Chicago will help your group relax and learn skills they can apply in their own lives beyond the office.

The Chicago area is a great place to plan a team retreat, especially for local companies or remote teams gathering in the Midwest. With a world-class art and culinary scene, as well as plenty of options for getting out into nature, Chicago is ideal for taking a weekend trip or booking an incredible Peerspace venue. With these nine retreat activities in Chicago, you’ll be sure to find something that will help bond your team.

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