Discover deep dish pizza, jazz music and more with co-workers in the Windy City.

Explore activities

Chicago is known for a lot of things from it’s beautiful architecture to 1920’s mobsters and culinary delights like deep dish pizza and Chicago-style hotdogs. Add to that scenic river views and a bustling music scene, and you’ve got an ideal spot to host your next team retreat.

From culinary tours to skyline cruises, there’s plenty of opportunity to bond with coworkers, build skills and make memories on a visit to Chi-Town. 

If you’re planning an upcoming retreat to Chicago, keep reading for our selection of the best team building experiences the city has to offer!


We work with our network of partners to provide you the best local and authentic experience around. You can book these activities exclusively as part of the company retreat package.

Explore Chicago’s culinary scene on a food tour

  • Explore the city of Chicago from a unique perspective as you dive into the history and culture of it’s culinary scene on a group food tour.
  • An experienced guide will share information about the city’s food history, local hotspots and fun facts about Chicago’s best eats.
  • Typically this experience lasts about three hours so be sure to set aside about half a day and wear proper footwear as you’ll be walking quite a bit!
  • Chicago offers tons of options to accommodate different dietary restrictions like vegetarianism or gluten allergies, making this an accessible experience for almost every team member.
  • These tours offer a great, private experience for team’s and can be totally customized to meet the requirements of your budget and group size.

Discover Chicago’s skyline on a boat cruise

  • Chicago is known for its impressive architecture and what better way to experience the skyline than through a boat cruise along the city’s waterways. 
  • Your tour guide will offer a ton of great information on the city’s history and culture while highlighting all of the best sites in Chicago.
  • The city offers a variety of different cruising options, providing a range of opportunities depending on your team’s needs and budget.
  • On most cruises you’ll even have the option to indulge in some drinks and light snacks while you tour.
  • Long sleeves and bug spray are a good idea for this activity during the summer months though as the bugs can be plentiful out on the water!

Problem-solve your way through an escape room

  • Escape rooms offer an awesome way to build on teamwork, communication and problem-solving skills while bonding with co-workers as you work together to solve the puzzle and beat the clock.
  • Staff are available onsite to answer any questions and help you through the experience and will even walk you through the solution if you run out of time.
  • Some facilities in Chicago offer VR options adding a bonus element of immersion to your experience.
  • This is a flexible team building option for groups of all sizes as you can add additional rooms to your booking at most locations to accommodate larger numbers.
  • Generally, this is a fairly affordable team building experience and works well for teams on a wide range of budgets.

Indulge in your sweet tooth with a baking class

  • From cookie decorating to learning how to make a french macaron, sweeten your next team building experience with a baking workshop.
  • A trained staff member will lead your activity offering tips, knowledge and hands-on techniques to make your very own sweet treats.
  • The facility will provide you with all of the tools and ingredients you need so all you need to do is show up hungry and ready to learn something new!
  • You’ll work together with team members as well as independently to bake your creations. Plus, you can hang out afterwards as you socialize and enjoy the final results.
  • This tends to be a pricier team building experience and typically has a maximum class size of 12-15 participants so may not be a great fit for larger groups.

Build real skills in a virtual space with a VR experience

  • Test your communication, collaboration and cooperation skills with a virtual reality experience in one of Chicago’s VR event spaces.
  • You and your team will be provided with everything you need for a great experience including multiple headsets and controllers and the option to add on more headsets as needed.
  • Most facilities offer a wide range of options to accommodate different sized teams from small groups of under fifteen to up to ninety participants. 
  • Typically you’ll be provided with a set number of hours for your activity allowing you to play as many games and rounds as you’d like within your allotted slot.
  • Many VR spaces offer the option of catering and/or bar service so you can snack and socialize between games.
  • This team building experience runs on the higher end for pricing so may not be accessible to larger teams working within a tight budget.

Get creative with a crafting workshop

  • Spark creativity while making a unique keepsake to remember your retreat with a group crafting experience.
  • You’ll be able to select from a variety of popular craft kits and an instructor will take you through each step in creating your final piece while leaving plenty of flexibility for you to customize and make your project truly your own.
  • Some venues in Chicago even offer virtual experiences providing added flexibility depending on your location. 
  • Often there is an option to bring your own drinks and snacks which is a big bonus, especially if your activity is running over a mealtime. 
  • This is a relatively affordable team-building experience for those on a budget and you’ll be provided with all of the tools and materials needed to create your keepsake.

Race to the finish at the go kart track

  • Race your way through fun-filled, friendly competition with a team building experience at the go kart track.
  • Time team members individually to see who can make it around the track the quickest or race in teams to see which departments grab the best times.
  • Beyond racing, some go karting locations provide additional team building activities such as pit crew challenges and other skill-testing games involving the karts.
  • Onsite staff will provide you with safety equipment like helmets but make sure to wear secure footwear and comfortable clothing for getting in and out of the karts.
  • Many facilities also provide additional opportunities for team time off the track such as snack bars, arcades and private meeting spaces where you can socialize between and after races. 

Create your own masterpiece with a paint night

  • Paint nights offer a fun, accessible and creative way to bond with team members as you work on creating your very own work of art.
  • You’ll paint at your own pace while instructors showcase various painting techniques and suggestions to apply to your own masterpiece.
  • You’ll be provided with all the materials and tools you’ll need, including a variety of paints, aprons and canvases - plus, they’ll even take care of the clean-up.
  • These experiences typically also include a BYOB and food option so you can sip and snack throughout the activity.
  • This type of experience is generally budget-friendly, especially if you can find a discount through websites like Groupon.

Test your aim with axe-throwing

  • Build a new skill while bonding with teammates through an axe-throwing experience during your next retreat.
  • An instructor will demonstrate everything you need to know to make this activity safe and beginner-friendly - just make sure to wear close-toed shoes!
  • Most facilities also offer a selection of drinks and snacks, or the option to bring your own, providing a great way for team members to keep occupied between turns.
  • Consider competing individually to see who has the best aim or break off into teams to work together to score the most points.
  • The price for this experience is typically budget-friendly and with the option to book multiple laneways it’s a great experience for team’s of all sizes.

Fill your appetite with a cooking class

  • If you’re looking for a fun and immersive alternative to a traditional team lunch or dinner, considering booking a group cooking class for your next retreat! 
  • An onsite chef will take your group through every step of the cooking process to make a delicious, 5-star meal completely from scratch.
  • You and your team will be able to build on your cooking skills, try new ingredients and work collaboratively to prepare your dish.
  • Not only is this a great opportunity to work together as your prep and cook your meal but it also offers a wonderful social experience as you sit down together to enjoy the final result.
  • This can be a bit of a pricier team building experience but if your budget allows it’s a great way to create a more dynamic team dining experience.

Would you like to book any of these activities?

(You can book these activities exclusively as a part of our retreat package)

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Team building activities in other Surf Office locations