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Chicago is the country's third most populous city, much to the dismay of the visionaries who dreamt Chicago would one day surpass New York City in its grandeur.
Nevertheless, Chicago has developed a unique character with its beautiful parks, impressive high-rise structures and iconic art and entertainment scene. These attributes have made the city a popular tourist attraction and an exciting location for a corporate offsite retreat.
There are few cities in the world with more cultural diversity than Chicago. A drive through the city is like a trip around the world as you pass myriad cafés, restaurants, clothing outlets and grocery stores.
This mixed culture is reflected too in the variety of team-building activities on offer. In a single day, your team can learn stand-up paddleboarding, hop on a boat cruise, play volleyball on the beach and sing their hearts out at a karaoke bar!
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We've put together a list of
team-building activities for company retreats in
Chicago
, including options that work well for both small and large teams.
Along the Chicago Riverwalk, Millennium Park, and vibrant areas like West Loop, this Chicago retreat agenda combines structured sessions with an architecture or food-focused experience and relaxed evenings in the city.
Chicago is a strong option for teams that want a big-city experience with architecture, food, and lakefront views. It combines business-friendly infrastructure with a lively social scene, making it easy to balance work sessions with memorable group experiences.
Chicago is highly accessible via two major airports, O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare is about 30–45 minutes from downtown via the CTA Blue Line or taxi, making arrivals relatively straightforward for large groups.
Late spring and early autumn tend to offer the best conditions, with temperatures typically ranging from 60–75°F. Summers are lively but can be humid, while winters are cold and better suited for indoor-focused retreats.
The Loop is ideal for business-focused stays and easy logistics, River North offers great dining and nightlife, West Loop has a more modern and food-driven atmosphere, and Lincoln Park provides a quieter, more residential feel.
Chicago stands out for its mix of architecture, culture, and accessibility. The city feels more structured and navigable than many large US destinations, which helps teams plan a company retreat in Chicago without complex logistics.
Groups often choose architecture boat tours on the Chicago River, improv workshops at Second City, food tours in West Loop, lakefront bike rides, or sports events depending on the season.
A typical Chicago retreat runs for about three to four days, which allows teams to include structured sessions, one or two standout activities, and group dinners without overloading the agenda.
Chicago sits in the mid-to-high range for US cities. While not as costly as New York or San Francisco, accommodation and dining can still add up, though there are enough options to adapt to different budgets.
Within 1 to 2 hours, teams can head to Lake Geneva in Wisconsin for a more relaxed lakeside setting, or explore nearby nature areas like Starved Rock State Park for hiking and outdoor activities.
Chicago’s food scene is a major highlight, from deep-dish pizza and steakhouses to Michelin-starred restaurants. Group dinners, food tours, and private dining experiences are easy to organize across the city.
We got incredibly positive feedback. Many people said it was the best offsite we've ever had. So that's obviously the most important thing from like an organizational point of view. It was super nice working with you guys. I really enjoyed it. It was the first year we had an agency like you guys on board and it did really help, especially now having a much bigger team.
We did send a survey to everyone after the event. And the feedback was very positive. Everyone loved the hotel. People were saying that the food at the venue was very good, which I agree with. The rooms were great. The meeting space was perfect for us. Obviously the beach and the area were perfect. I think it was a great location for our team. There were some people that said this was the best summit they’ve attended.
The feedback has been impeccable. Everybody loved the hotel, loved the staff, loved the support from Surf Office, everything. All the expectations were, you know, not even just met, but went beyond. We loved the way we were taken care of.
The overall feedback was really fantastic. Everybody really liked the venue. They really liked being in the same location. We had a wonderful partnership and we’d love to work with you again.
We walked into it anxious. We walked away from it absolutely amazed by the results. It was so well organized. I would never have been able to do that alone, you pulled that off entirely. It was amazing. The team is buzzing! It blew people away. It definitely blew us away.
I was stressed out before the retreat cause I never did the planning. As soon as we arrived to the hotel, they knew everything and I didn’t have to worry about anything. Big thumbs up to the Surf Office team for the general flexibility, and for the communication.
It was absolutely perfect. There wasn’t one thing that I can criticize. We had a fantastic time, really really good. It went so smoothly, everybody was very happy. Anybody that asked now about how the offsite went, I just say: “It was amazing, you only can use 1 company, you don’t need to use anybody else”.
Amazing. It was I think a really lifelong memory. I think the whole team had a really great time. I never could do this without Surf Office.
It was an awesome experience. It went super smooth, the drivers were on time, food was great, and the flexibility of the hotel was great. We had a truly amazing time and all because of your great work and preparations – you were like the magic fairies that organised everything so beautifully!
The most popular team building activities are surf lessons, SUP lessons and tapas night but there are plenty more to choose from.
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Join the club of innovative companies which organise
retreats with Surf Office.
