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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.
In full transparency, everyone loved it. People are still talking about it. The main goal was team bonding and you helped me to reach it.
Everyone was delighted by the venue, the activities, the transfer coordination and everything! Long live Surf Office! Can’t wait to plan our next company retreat with you :)
Our team offsite retreat was excellent - great food, weather and activities. Even the people that couldn't attend wished they could have made it. And the location was perfect. Surf Office - Thank you very much for your help and support with planning and organization - and Beatriz our retreat manager was fantastic - fast, efficient and always kept us informed. It really made the difference. It really did!
Surf Office helped us plan our 60 person staff retreat, scoping locations, venues, restaurants, activities, and more. Angela was really on top of it and paid close attention to all of the details. Definitely saved us time on research and back-and-forth with all of the various contact persons!
We went into talks with SurfOffice and hit it off with the founders to make this happen. Theres a team that will guide you through the choice and a platform for when you are to arrive with an agenda. Our team likes to bring in community members to these types of events and the crew is excited. The onboarding is going well and we paid the deposit, and we're looking forward to the trip. Our party had to reduce significantly due to constraints and the team has been accomodating so far. 5* everyone had a good time and Rayna on site made everyone feel comfortable.
The location was great, the areas dedicated to us were amazing and all things we asked for were there - also, I love the shared dashboard to organize.
I recently worked with Surf Office to organize an offsite retreat for my company in Gran Canaria, and I couldn't be happier with the experience! Beatriz, the retreat planner, was incredible. From start to finish, she was exceptionally organized, responsive, and attentive to every detail. Planning a retreat for a team can be daunting, but Beatriz made the process seamless. She answered all my questions quickly and thoroughly, and her recommendations were spot-on. The offsite itself was beyond amazing – the accommodations and activities were perfectly tailored to our team’s needs. Surf Office took all the stress out of planning and delivered an unforgettable experience for our group. I highly recommend them to anyone looking to plan a work retreat. If you’re lucky enough to have Beatriz as your planner, you’re in great hands!
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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retreats with Surf Office.
