.webp)
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!
.jpg)
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.
Surf Office was amazing to work with - from the initial introductory call to the final day of our corporate retreat! They are well-organised, transparent, super reliable and the communication throughout the planning and execution phase was prompt and clear. We are looking forward to working with them for future company retreats.
I had the absolute pleasure of working with Elke and Álvaro to plan our onsite, and I genuinely couldn’t have asked for a better experience. From the very beginning, they were incredibly friendly, responsive, and genuinely enthusiastic about helping us create a great event. Elke was so thoughtful and organized, always making sure every little detail was covered and keeping everything running smoothly. She brought such a positive energy to the process — she was super approachable and made collaboration easy and fun. Throughout the entire planning period, they both went above and beyond to support us. I really appreciated how proactive they were in anticipating our needs, and how enjoyable every interaction was. It truly felt like working with partners who cared as much about the success of our onsite as we did. Thank you, Elke and Álvaro, for being such a joy to work with! I’d happily work with you both again any time.
It's our second year working with Surf Office for our company offsite (30 pax first year, and 42 pax second year), and we're super happy! This year our offsite was a huge success, with direct impact on our employees' satisfaction, company culture, and alignment with our mission. The week they put together for us was perfect on all fronts: venue selection, logistics, activities, last-minute changes - everything was super well executed. Couldn't recommend them more! And... I know whom we're working with next year!
Working with Surf Office was a great experience from start to finish. Communication was smooth, the planning was thoughtful, and the platform made coordination easy. We really appreciated the well-curated suggestions for locations, activities, and restaurants – everything felt carefully considered. Beyond that, the setup created a great team atmosphere, making it easy to connect and enjoy our time together. We would definitely recommend Surf Office to any team looking for a well-organized and inspiring retreat.
Danielle, Giselle and the SurfOffice team were extremely cooperative, understanding and flexible to support my team’s 80-person offsite in Belgrade, Serbia. From being patient with our company’s lengthy vendor due diligence and procurement process, to responding swiftly when an attendee misplaced her passport - everything went really smoothly. Working with them took a huge load off our shoulders and their relationships with hotels/activities/venues also helped us secure good deals. Would definitely recommend their services to any company who’s looking to plan for an enjoyable team offsite.
We recently organized our company offsite with SurfOffice, and we couldn’t be happier with the experience. From the very beginning: The location selection and contract negotiations with Giselle, to the actual planning and execution of the offsite together with Elke, everything was handled exceptionally well. Working with Elke was truly outstanding. She was incredibly proactive, always thinking several steps ahead, and responded extremely quickly to every question or change. She managed to get fast answers from all providers: from transport companies to hotels and local activity partners- and did so with a consistently friendly and professional attitude. Thanks to her dedication, we had little organizational workload on our side, and we always felt fully supported. The offsite turned out to be an amazing experience for our whole team, and we’re certain we couldn’t have organized something like this on our own. SurfOffice played a huge role in making our offsite in Kemer such a success, and we can wholeheartedly recommend them to any company planning an offsite for a larger group.
Sara was fantastic in organising our company trip to Istanbul - she was quick to reply, offered great solutions to issues, and made the trip itself seamless and enjoyable. Already looking forward to the next one!
Expertise and competence in service. Friendly, helpful, and respectful communication. Comfortable, welcoming, and inspiring surroundings.
This was our second year working with Surf to plan our annual company retreat, and once again, they smashed it. We had a beautiful, restorative and fun retreat just outside of Barcelona that the whole team loved. It was so lovely to have the team's support in planning such a complex event, and they did a great job at helping us stay within budget. Great experience overall.
The most popular team building activities are surf lessons, SUP lessons and tapas night but there are plenty more to choose from.
Our closest location
Closest airport
Currency
Join the club of innovative companies which organise
retreats with Surf Office.
