A unique offsite experience in Chicago

A colourful city of endless opportunity

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.

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Why 

Chicago

?

Why choose 

Chicago

for a 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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Team building activities in

Chicago

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.

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Yoga in Chicago
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Karaoke in Chicago
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Kayaking in Chicago
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Food Tour in Chicago
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Laser Tag in Chicago
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Go Karting in Chicago
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Volleyball in Chicago
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Boat Cruise in Chicago

Sample

Chicago

Retreat Itinerary

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.

Day 1: Arrival & Downtown Introduction

City arrival, skyline views & easy start

  • 13:00–17:00Airport transfers & hotel check-in (Downtown / River North)
  • 18:00–19:30Walk along the Chicago Riverwalk & Millennium Park
  • 20:00–22:30Group dinner in a classic Chicago restaurant
  • 22:30+Optional drinks in a rooftop bar

Day 2: Work & Chicago Experience

Focused sessions with a local highlight

  • 08:30–09:30Breakfast at hotel
  • 09:30–11:00Plenary session (team alignment & goals)
  • 11:00–11:30Coffee break
  • 11:30–13:00Breakout workshops
  • 13:00–14:30Lunch near the hotel
  • 14:30–16:00Workshops or brainstorming
  • 16:00–19:00Main activity: Architecture river cruise or deep-dish pizza tour
  • 20:00–22:30Dinner in West Loop

Day 3: Exploration & Final Evening

Flexible time & iconic city moments

  • 08:30–09:30Breakfast at hotel
  • 10:00–11:00Wrap-up session & key takeaways
  • 11:30–15:00Free time (Art Institute, shopping, or lakefront)
  • 15:00–18:00Relaxation or optional visit to Willis Tower Skydeck
  • 21:00–lateFarewell dinner with skyline views

Day 4: Departure

Easy wrap-up

  • 08:30–10:30Breakfast & informal chats
  • FlexibleAirport transfers & departures

United States retreat experiences

FAQs about company retreats in

Chicago

Is Chicago a good destination for a corporate offsite?

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.

How easy is it to travel to Chicago for a team retreat?

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.

What is the best time of year to plan a corporate retreat in Chicago?

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.

Which areas are best to stay in Chicago for a company retreat?

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.

What makes Chicago different from other corporate offsite destinations?

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.

What team-building activities can you organize in Chicago?

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.

How long should a company retreat in Chicago last?

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.

Is Chicago an expensive destination for corporate retreats?

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.

What are the best day trips for a team retreat in Chicago?

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.

What kind of food and dining experiences can teams expect in Chicago?

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.

💛 Wall of love 💛

The SurfOffice team helped me organise a great offsite abroad for my distributed team of 16 and the experience was seamless. Their clear communication made planning easy, and they thought of everything we might need. They have a great selection of hotels and experiences, helping us stay within budget without compromising on quality. What especially stood out was their real-time availability during the event, which helped us quickly solve a few last-minute issues.

Laura
Community & Events Manager

We recently worked with Surf Office to organize a company retreat in Lisbon, and the experience was nothing short of exceptional. From the very beginning, Simon was incredibly patient and supportive, helping us navigate multiple destination changes until we finally landed on Lisbon. His calm demeanor and willingness to ensure we found the perfect location made the planning process much smoother. Once we signed the contracts, Cristi took over and was an absolute star. Her patience, clear communication, and flexibility made all the difference. She understood our brief, even in its most creative form, and worked tirelessly to bring it to life. Cristi kept us on budget, coordinated seamlessly with the right production team, and managed everything through an intuitive dashboard on Coda. She was always a step ahead, anticipating our needs before we even voiced them. On the ground, Fernanda was a force to be reckoned with! She ensured that venues delivered on time and to the highest standards, making sure every detail was executed flawlessly. What truly set Surf Office apart was their ability to make us feel like a collective team rather than just another client. They handled sensitive information with discretion, tackled challenges with calm professionalism, and ultimately delivered an unforgettable retreat. We would work with Surf Office again in a heartbeat and highly recommend them to anyone looking to plan a seamless, well-executed offsite.

Medhavi
Talent Acquisition Manager

From the very first contact to the last goodbye, Surf Office was an incredible company to work with for our company retreat in Portugal. The customer service was top tier and every single person I interacted with was absolutely lovely, professional and so helpful.

Tracy
Head of Human Resources

We recently had our company retreat in Spain which was organized together with Surf Office and the experience exceptional. From the initial planning stages to the final details, the Surf Office team was professional, attentive, and incredibly helpful. They provided tailored recommendations for a venue and their local expertise and network made the entire process smooth and stress-free. The seamless coordination of accommodation, transportation, and activities allowed us to focus on creating meaningful connections within our team without worrying about logistics. The retreat itself was a huge success, and a big part of that was thanks to Surf Office's ability to anticipate our needs and adapt to last-minute changes. I would like to give a special shoutout to Romane who is an organization wizard and made sure everything works out as planned, Fernanda who was our on-site support and did an exceptional job even for the very short-term requests. If you're looking for a reliable partner to help organize your next retreat, I highly recommend Surf Office. Their expertise, attention to detail, and dedication to creating memorable experiences are unmatched. Thank you!

Alisha
Culture Manager

We have organized company retreats for our distributed 30 people team multiple times with Surf Office and the team has loved it every time. Surf Office has some great venues as part of their portfolio and do a great job helping to facilitate pretty much everything from accommodation, food, activities, airport transfers etc.

Kaylie
Director of People

Candela over at Surf helped us to organise our first ever team retreat in Portugal for 30 odd people (which included +1s and small children.) It honestly couldn't have been more perfect. Every detail was seen to and we felt completely supported. Our team came away from that trip feeling like a proper little family. Such wonderful memories. We honestly could never have done this without Surf and would recommend to anyone.

Gemma
Studio manager

Surf Office made planning our 20 person offsite a breeze! They found the perfect location for us, advised on places we weren't originally considering, and the organization/logistics were very smooth. As a small people team, having this extra help makes a world of a difference. Our team had a great time!

Leila
Head of People

We had a fantastic experience partnering with Surf Office for our 3-day company retreat in Costa Brava. From the early planning stages to the end of the event, everything ran smoothly and professionally. We first worked with Anthony, our Company Retreat Consultant, who helped us choose the right package. He was responsive, approachable, and clearly experienced—making it easy to select the hotel, which suited our needs perfectly. From there, we were supported by Romane, our dedicated Retreat Manager. She was absolutely great—well-organized, proactive, and always ready with thoughtful recommendations and local insights. Whether it was fine-tuning the schedule, adjusting logistics, or booking group activities like kayaking and hiking, she made sure every detail was handled. The mix of work sessions, team-building, and social time was just right. The hotel was comfortable, the activities were fun and well-coordinated, and the team dinners and beach events added a special touch. Everyone had a great time and felt the experience helped strengthen our team dynamics. Surf Office made it easy to plan and execute a retreat for 65 people without stress. We’d absolutely recommend them to any team looking to run an effective and memorable offsite—and we’ll definitely be working with them again.

Giulia
International HR Advisor

We had the pleasure of working with Surf Office to organise our annual company offsite in Portugal and the experience exceeded all expectations. From the initial planning stages to the final event, the team demonstrated outstanding professionalism, attention to detail and a true commitment to making our event a success. Every aspect of the offsite was handled seamlessly, including venue selection, team-building activities and logistics. They have a deep knowledge and network of local and trusted vendors.

Helen
Director of Market Intelligence

Team building activities

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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