Whether your company or team is based in Chicago or you’re traveling to the Windy City for an executive retreat, conference, or other team event, Chicago is packed with team building activities that go far beyond the typical happy hour (although the city does boast some incredible rooftop patios and breweries!).
From the picturesque Chicago River to buzzing neighborhoods like West Loop and River North, Chicago offers a mix of indoor and outdoor team building experiences for every group and season. And trust us: seasonality matters. While any Chicagoan will tell you that summertime Chi offers unparalleled outdoor experiences, the city also offers a plethora of creative indoor activities for colder and rainier team building occasions.
To help you find the right activity for your group, we’ve curated a list of our favorite team building events and experiences across the city.
1. Team Building Scavenger Hunts
With its diverse neighborhoods, unique parks and sculptures, and one-of-a-kind museums, Chicago offers great ways to bond with your team while exploring the city together. See the best of the city and introduce some friendly competition with a scavenger hunt from Watson Adventures! Teams collaborate, compete, and solve puzzles on unique scavenger hunts through neighborhoods, museums, zoos, and more.
Our most popular scavenger hunts in the Windy City include…
- For a traditional scavenger hunt: Secrets of the Loop Scavenger Hunt
A rave from one participant: “Our corporate finance team participated in the Secrets of the Loop Scavenger Hunt. We had an absolute blast! The scavenger hunt was extremely engaging with the absolute right scale of challenge. My entire team of 30 people work and live in Chicago, and the hunt brought us into buildings we’ve never been into before and guided our attention to details that we otherwise would have overlooked. Thank you, Watson Adventures!” - For mystery lovers: Museum of Natural Hysteria Scavenger Hunt at the Field Museum
- For food lovers: Munch Around Fulton Market & The West Loop
Want more options? Explore all Chicago scavenger hunts.
DIY or Hosted? Hosted
Location: Everywhere anywhere, including such places as Navy Pier, the Lincoln Park Zoo, the Art Institute of Chicago, and neighborhoods like Wicker Park
Group Size: Groups large and small (6-150+)
2. Improv Workshops
If you’re going to do improv anywhere, do it in the city that basically invented modern improv. Jump into fast-paced exercises that reward quick thinking, listening, and saying “yes, and…” instead of shutting ideas down. Improv-based team building exercises are equal parts hilarious and surprisingly insightful—perfect for loosening people up, breaking down hierarchy, and getting even the quietest team members involved.
DIY or Hosted? Hosted
Locations: Improv theaters around the city including Second City, io Theater, Logan Square Improv, and more!
Group Size: Small to medium groups
3. Shuffleboard at Royal Palms
If you want something competitive without being too intense, shuffleboard hits the sweet spot. Royal Palms Shuffleboard Club brings tropical energy to indoor events with courts, cocktails, and plenty of space for groups to spread out and mingle.
DIY or Hosted? Hosted
Location: Logan Square
Group Size: Small to medium groups
4. Food Tours in the West Loop & Beyond
Chicago is a world-class food city, so if your team is full of foodies (or just really hungry!), consider going beyond the traditional team dinner to make some truly lasting memories. Consider a guided tour or even a food scavenger hunt to add clues, friendly competition, and problem solving to the mix. Munch your way through hotspots like the West Loop/Fulton Market, Logan Square, or River North to explore the city and its best bites.
Watson Adventures’ “Munch Around Fulton Market/West Loop Food Scavenger Hunt”
DIY or Hosted? Hosted
Location: West Loop, River North, Wicker Park
Group Size: All sizes
5. Brewery & Distillery Tours
Chicago’s craft scene is strong, and a brewery or distillery tour is an easy win for team bonding. You’ll get a mix of guided tastings, behind-the-scenes insights, and just enough structure to keep things organized without feeling forced. It’s especially great for exploring neighborhoods beyond the Loop and River North, as well as for end-of-day events or teams that prefer a more social, low-pressure vibe. Just make sure to consider options for your non-drinking colleagues.
DIY or Hosted? Hosted
Locations: Revolution Brewing (Avondale), Koval (Ravenswood), Goose Island (multiple locations), and more.
Group Size: Medium groups
6. Architecture River Cruises
You can’t talk about Chicago without talking about architecture, and there’s no better way to experience it than from the water. A guided cruise along the Chicago River gives your team a shared experience that’s equal parts relaxing and impressive, with plenty of built-in conversation starters. It’s not your typical “high-energy” activity, but it’s perfect for teams that bond best over great views, good stories, and a drink in hand.
DIY or Hosted? Hosted
Location: Chicago River / downtown
Group Size: Medium to large groups
7. WhirlyBall
WhirlyBall is what happens when bumper cars, basketball, and lacrosse collide…and somehow, it works. Teams cruise around in bumper cars trying to score points while inevitably crashing into each other and laughing the whole time. It’s chaotic, high-energy, and perfect for breaking down barriers fast.
DIY or Hosted? Hosted
Location: Bucktown (right off the highway)
Group Size: Medium to large groups
8. Ping Pong Social Clubs
Who knew you could turn a simple game of ping pong into a party?! Chicago’s ping pong clubs blend casual competition with music, drinks, and a lively atmosphere that keeps things feeling social rather than overly structured. It’s easy to jump in and out of games, making it ideal for mixed groups where not everyone wants to be “on” the whole time.
DIY or Hosted? Hosted
Location: River North and surrounding neighborhoods
Group Size: Small to medium groups
9. Beach Day
If you’re looking for a laid-back, warm-weather company outing that can accommodate large groups, consider a classic Chicago beach day. Large beaches like Montrose and North Avenue offer plenty of space, volleyball courts, and more to keep groups entertained. For a convenient option close to downtown (as well as great city views!), consider Oak Street Beach. Beach volleyball not your team’s speed? Pack activities like Spikeball or Beach Bocce instead, or simply load a cooler up with snacks, sandwiches, seltzers, and sunscreen for a lower-key group get-together.
DIY or Hosted? DIY
Location: North Avenue Beach, Montrose Beach, Oak Street Beach, and more
Group Size: Medium to large groups
10. Murder Mystery Games
If your team loves a good storyline, murder mystery events turn everyone into detectives, suspects, or both. These experiences mix mystery, problem solving, and collaboration as teams piece together clues and try to crack the case. It’s a great way to get people interacting in new ways.
Go for a traditional murder mystery dinner party or opt for a murder-mystery-meets-scavenger-hunt game that allows your team to get out and about while still solving mysteries:
- Field Museum: The Field of Screams Murder Mystery Scavenger Hunt
- The Art Institute: Murder at the Art Museum
- The Loop (outdoor): Murder in the Loop
DIY or Hosted? Hosted
Location: Nearly anywhere—from your own office to museums and Chicago neighborhoods!
Group Size: For a classic murder mystery dinner party, small groups work best. For medium to large groups, murder mystery scavenger hunts are a better fit.
11. Outdoor Field Days & Lawn Games
When the weather cooperates, take things outside. Field days with games like cornhole, giant Jenga, relay races, or mini competitions give teams a chance to move, laugh, and tap into some low-stakes nostalgia. It’s simple, flexible, and surprisingly effective for team bonding.
DIY or Hosted? Both
Location: Parks and outdoor spaces across Chicago
Group Size: Medium to large groups
12. Trivia Nights & Competitions
Trivia is the great equalizer—everyone knows something, and that’s what makes it fun. Whether you host it at a bar or bring in a professional trivia company for a hosted trivia game, it’s an easy way to spark friendly competition and get people talking. Add themed rounds or inside-company questions for extra engagement.
DIY or Hosted? Both
Location: Bars, offices, or event spaces
Group Size: Any
13. Kayaking on the Chicago River
For a more active (and very Chicago) experience, get your team out on the water. Kayaking along the Chicago River offers a unique perspective of the city while requiring just enough coordination to count as team building. It’s best for smaller, more adventurous groups—just beware of the rogue pontoon boats captained by overzealous Chicagoans!
DIY or Hosted? Hosted
Location: Chicago Riverwalk
Group Size: Small groups
14. Axe Throwing
There’s something oddly satisfying about hurling an axe at a target after a long week. Axe throwing venues keep things organized with coaches, structured games, and just enough competition to keep it interesting. It’s simple, a little edgy, and a guaranteed conversation starter.
DIY or Hosted? Hosted
Location: Multiple indoor venues across Chicago
Group Size: Small to medium groups
15. Cooking Classes
Cooking classes are one of the few team building activities where collaboration literally creates something tangible (and delicious). Teams work together to prep, cook, and plate dishes—usually with a bit of friendly competition mixed in. Bonus: everyone leaves full and slightly impressed with themselves.
DIY or Hosted? Hosted
Location: West Loop and other culinary hubs
Group Size: Small to medium groups
16. A Trip to the Museum
A museum outing is a classic for a reason, and Chicago gives you no shortage of world-class options, from the Art Institute of Chicago to the Field Museum to the Museum of Science and Industry. Each is packed with enough to spark curiosity and conversation.
Want to actually get your team interacting so the outing feels less like a field trip? Turn the experience into a game. A museum scavenger hunt—like those from Watson Adventures—transforms passive wandering into fast-paced problem solving, with teams racing to crack clues, notice details they’d otherwise miss, and collaborate along the way. It’s an easy way to scale a museum outing for large groups.
- For art lovers: The Art Attack Scavenger Hunt at the Art Institute of Chicago
- For history buffs: Escape the Chicago History Museum
- For groups who want a little bit of everything: The Museum of Natural Hysteria Scavenger Hunt at the Field Museum
DIY or Hosted? Hosted
Location: The Loop and Museum Campus
Group Size: All sizes
17. Rooftop Happy Hours
It’s not summertime in Chicago without a rooftop hang, and sometimes the best team building is just giving people a great place to connect. Chicago’s rooftop bars offer skyline views, good food, and a relaxed atmosphere that encourages conversation. It’s a strong option for teams that prefer social bonding over structured activities.
DIY or Hosted? DIY
Location: Citywide, but especially River North and The Loop
Group Size: Small to medium groups
18. Boat Charters on Lake Michigan
If you want something that feels a little more elevated, a private boat charter on Lake Michigan delivers. You get skyline views, fresh air, and a built-in sense of occasion—ideal for celebrating milestones or hosting higher-end corporate events.
DIY or Hosted? Hosted
Location: Lake Michigan / Navy Pier area
Group Size: Medium to large groups
19. Cheering on Chicago Teams
Few things bring people together like cheering for the same team. Group outings to see Chicago teams at iconic stadiums like Wrigley Field (Chicago Cubs) and Soldier Field (Chicago Bears) are a great way to get outdoors and enjoy the warmer months (or brave the cold). Rather avoid the winter winds? Head for indoor arenas to cheer on the Blackhawks or Bulls for a shared experience with built-in excitement. It’s low effort, high energy, and easy to scale
DIY or Hosted? DIY
Location: Stadiums across Chicago
Group Size: Medium to large groups
20. Volunteering & Service Projects
Team building doesn’t always have to be about competition—it can also be about purpose. Volunteering together, whether it’s packing meals, supporting local nonprofits, or community clean-ups, builds camaraderie while giving back. It’s especially meaningful for mission-driven teams.
DIY or Hosted? Both
Location: Various organizations across Chicago
Group Size: Flexible
How to Plan a Corporate Team Building Event in Chicago
Planning a team building event in the Second City doesn’t have to turn into a second job. The trick is picking something that fits your group, not overcomplicating it, and getting help from the pros when you need it. Here’s what to consider:
- Start with your group size: Big group? You’ll want something that scales without turning into chaos—think structured games or reserved spaces. Smaller team? You’ve got more flexibility with things like cooking classes or hands-on workshops.
- Be honest about your goals: Are you trying to boost collaboration, celebrate a win, or just get people talking to each other like humans again? High-energy, problem-solving activities build teamwork fast, while more relaxed experiences are better for connection and conversation.
- Plan for Chicago weather (seriously): Winter = go indoors and stay there. Spring, summer, and fall open things up: neighborhoods, parks, the lakefront, and the Chicago River all become part of your playing field.
- Don’t underestimate logistics: Coordinating locations, timing, and group flow for a large team can get complicated fast. If you’re already juggling a dozen other things, this is where most “simple” plans fall apart. Which leads us to our last tip…
- When in doubt, don’t DIY it: Working with an experienced event company means you’re not stuck herding cats or troubleshooting in real time. Watson Adventures plans and hosts renowned Chicago team building events—from scavenger hunts to murder mystery games and trivia—that are built to engage groups small to large (even 150+!) without the planning headache.
Start Planning Your Best Team Building Event Yet
Contact us to learn more and start planning your Chicago team building game! Groups of all sizes are welcome.