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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 had an unforgettable company offsite in Panama with 19 team members, and everything from start to finish was exceptional. The food was incredible, authentic, fresh, and consistently delicious throughout the trip. Our hotel stay was fantastic, especially the strong air conditioning, which was a huge plus in the tropical heat! Surf Office did an outstanding job managing everything. As a small team, using them was a huge help to ensure we hit deadlines, found team-building activities, and had a good selection of food choices. They were professional, highly organized, and incredibly on top of every detail, making the experience smooth and stress-free for everyone involved. From scheduling to coordination and on-the-ground support, they handled it all flawlessly. Transportation during the event was well-organized and reliable, making it easy to move between activities without a hitch. Overall, this was a 10/10 experience. Highly recommend this destination and working with Surf Office for any team looking to recharge, connect, and be inspired in a beautiful location. We will absolutely be using them again for our next company off site!
I had a great experience working with Surf Office! Elke and Alvaro were extremely helpful throughout the process and I always felt confident our retreat planning was in good hands. We've held 2 retreats working Surf Office and would recommend them to anyone looking for help planning a company retreat.
We are a 100% remote Software Company that has been doing self organized Teamevents since 2016. They are a very important part of our company culture and something the whole company is looking forward to throughout the year. As the company grew we have been searching for a partner to organize a Teamevent for 50 People in 2024 and have found the perfect one with Surf Office. The main advantage for us was not them taking over the main organization, it was that they just had the same vibe. You can find people who will organize a team retreat for you - but only a few will catch the right vibe and select the right venues - Surf Office does! Needless to say that the whole process was smooth and the organization was flawless. If you are a boring company, please do not hire them. But if you are a bunch of people that are working together and actually like each other, i would really give it a shot. For us, a Teamevent has never felt this easy.
We recently partnered with Surf Office to organize our company retreat in Osaka, Japan, and we couldn't be more pleased with the experience. From the outset, Surf Office showed exceptional ability to coordinate across time zones, manage the language barriers, and handling the logistical complexity of a group of 100+ people with ease and professionalism. The team from Surf Office were flexible, communicative, and proactive every step of the way. They helped us plan everything, from the event scheduling to restaurant reservations, hotel reservations for 100+ people, team activities, and last-minute changes They ensured the entire retreat was seamless, memorable, and highly energizing for our team. Thanks to their support we were able to focus on what mattered most: connecting as a team, exploring a new culture, and building lasting memories We highly recommend Surf Office to any company looking to run a world-class team offsite, especially in international destinations.
We went to Lisbon with 31 employees from all over the world. The event had been organised by SurfOffice/Elke. The hotel was top, the activities were top and the food was top. The communication with Surf O. was very good too, and it helped that Elke is a Dutch woman living in Lisbon. The coda app was not very handy at first, but turned out to be useful at the end/towards the event. We look back at a very successful All Company Meeting in Lisbon!
We can highly recommend Surfoffice for company retreats! From the very first contact until the end of our trip, everything went smoothly. Communication was consistently fast, reliable, and highly professional. A special thanks goes to Stef, who supported us throughout the entire organization process. She was always available, answered all our questions, and made the planning process extremely pleasant with her friendly and helpful approach. Lola also did an excellent job in finding the perfect accommodation for our group — her quick and competent assistance was invaluable. The accommodation itself was beautiful, with an incredibly kind host who took great care of our group and prepared delicious meals for us. Surfoffice provided us with a perfectly organized company trip — efficient planning, outstanding support, and a wonderful experience for the entire team. We are already looking forward to our next trip with Surfoffice!
SurfOffice delivered an absolutely outstanding service. Their attention to detail, responsiveness (literally day and night!), and presence throughout the entire process went far beyond our expectations. The whole team was a true pleasure to work with — professional, proactive, and always one step ahead. A special thank you to Cris, Romane, and Angela: you were exceptional. Your dedication, kindness, and efficiency made all the difference. Thank you again — we would 100% recommend SurfOffice and look forward to the next collaboration!
Great support, personalised service and great experience. Would highly recommend Surf Office services to any organisation. Their follow-up tools make it very easy to also communicate with your team.
I organized our company retreat with the help of SurfOffice, specifically with the help from Candela and Álvaro. They helped me tremendously, made sure important things were taken care of, deadlines were met and they made sure we could have a smooth experience with the company during the week - we had an absolute blast on Gran Canaria and the Team had an amazing week! The communication was absolute S-Tier. Clear, quick and always friendly, which made organizing an event very enjoyable, which normally is a rather monotone and sometimes even chaotic experience. I came into this without any event organization experience and leave with a "wow, this was smooth!". Thank you for this!
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.
