It’s no secret: since the rise of remote work, it’s become harder to cultivate a strong team culture with teams that are now hybrid. Now more than ever, it’s essential to promote connections between co-workers in order to keep them engaged and productive. What better way to promote synergy than organizing team building activities right in the heart of Chicago. 

Team building activities are an excellent way to foster better communication, promote creativity, and help establish teamwork within your company. So why not take your team out to the beautiful streets of Chicago to eat, play, and learn? Whether your team is based in and around Chicagoland, or traveling into the Windy City for team bonding, here are some five star (or should I say Four Star, as in the four stars on the Chicago flag) outdoor team building activities to explore for your group in Downtown Chicago.


Make It A Team Beach Day — Picnic, Volleyball Tournament and more! 

There’s nothing quite as iconic as a day out on the beach with the team, grilling, playing some games and enjoying the sunshine out of the office. This Midwestern Mecca sports over 20 beaches along Lake Michigan’s immaculate shoreline. Head over to Oak Street Beach for a lazy day in the sun. This beach is an excellent choice for teams with different tastes as there’s sand for those who want to sunbathe and a concrete section for those who want to avoid the sand.  No real beach hang would be complete without a volleyball tournament, so don’t forget to pack a net and a ball. Chair rentals are available during the summer months. There’s also a bar and restaurant called Whisper’s at Oak Street Beach so your team can continue its outdoor team building activities with a celebratory drink for the winners of the volleyball tournament, or an excellent consolation prize.

Add to your team beach day with activities in the water as well! 


See How Your Team Takes to Kayaking on Lake Michigan 

Tucked away in the East corner of Ohio Street beach you’ll find Bobby’s Kayak rental shack. Your one stop shop for all your city kayaking needs. With the option to rent single or double kayaks, you can be sure to find the right fit for everyone in the group. 

Have you ever gone kayaking in a tandem kayak and not talked to the other kayaker at all? The simple act of paddling requires clear and precise communication, the more you participate and work with your partner, the smoother the ride. This is an excellent option for outdoor team building with an emphasis on communication. 

Organize a kayak race to a point out in the water, or simply enjoy each other’s company paddling around the lake, while getting unparalleled views of Chicago’s famous skyline. This activity, although not year-round team building activities, is great for any time of day during the warmer months. 

Sunset kayaking is a particular favorite time for locals since you can watch the sun set over our beloved concrete jungle, and end the day on a positive team note. Sunset paddling events make for a great opportunity for your employees to bring along their significant others and/or families to enjoy the outing as well.

Forget the Team Potlucks, Take a Guided Food Tour as a Team!

Let the team enjoy each other’s company and the fantastic dishes of Chicago.

In every culture around the world, one thing remains true: our love of food. But no city does food quite like Chi Town. In the 1970’s, we used our food culture to attract tourists from all over the country. Have you ever wondered why the relish on a Chicago Hotdog is dyed neon green? Or why we Chicagoans have an almost religious hate for Ketchup. Or what about this deep-dish pizza, what exactly makes it different from all the other pizza our world has to offer? If these are questions that keep you up at night, then come take the Chicago Favorites Food Walking tour.  Your team will be able to try all the classic foods every Chicagoan and tourist alike must eat to get the full city experience and not only that, but you’ll leave knowing more about these foods’ origin stories. 

There are lunch and dinner food tours as well, with each tour lasting 3 hours exploring Chicago’s most iconic sites from the Wrigley building to the Palmer House Hotel (where the original brownie was invented) and everything in between. 

If the public tour times don’t work for your group, feel free to contact us to set up a private tour!  Walking tours run year round, so your team outing doesn’t have to wait until the weather turns nice enough to get outside. Don’t give them one more thing to do during the day, treat your team to good food and a good time out together. 

Go The Extra Mile For You Team with a Group Bike Tour

Does the group food tour sound almost like a homerun, but your team is made up of bike riders looking to bike Chicago together? Swap out the walking tour for a city food tour by bike! 

A city bike tour is great if you have new team members that have just moved to the city, or you’re hosting remote employees that haven’t been out in Chicago much. Even for those employees that have lived and worked in Chicago much of their life, a city bike tour can open their eyes to new possibilities and ideas — and be a conversation for the team later on.

You can experience more of the northside neighborhoods while drinking some of the finest local beers and learn about the foods that made this city famous. Check out the Bike, Bites, and Brew’s tour starting at the Bobby’s Bike Hike Headquarters near Navy Pier and bike up to Wrigley Field, home of the notorious Chicago Cubs. This guided tour is a great casual team activity that gets you all out of the office, on some bikes, exploring the city and loaded up with bites and brews along the way!

Or get to know the immigration culture here in Chicago on our West Side Foodie Ride Tour. One of the greatest examples of teamwork is the migrant communities that built our grand city.  

All bike tours start and end at Bobby’s Bike Hike Headquarters at 540 N Lake Shore Dr. Biking tours run from March through December, and all tours run rain or shine!

Rent Bikes for the Day and Make It A Team Scavenger Hunt on Bikes!

 Is your group looking for a small group team building activity or a large group team building activity? Either way, you can experience the great outdoors along Lake Michigan’s waterfront taking advantage of the Lakefront Trail on bikes. This city trail is an 18.5-mile walking and biking path spanning from South Shore Nature Sanctuary and Cultural center on the South Side and ending at Lane Beach on the North Side. This path was originally designated as a bike trail in 1963 thanks to our mayor at the time, Richard J. Daley. A major boon for the Lakefront Trail is its separated bike path and walking path that was just finished in 2018, making biking along the Lakefront easier and safer for everyone. 

Bike to Navy Pier, Lincoln Park Zoo, Buckingham Fountain and more. Add a little team competition to the day with a scavenger hunt on bikes! Use this Chicago scavenger hunt list or create your own. Add in time limits, picture rules, steals, or extra points for team fun facts along the way!

Rent your bikes through Bobby’s Bike Hike today, and start planning the ultimate scavenger hunt for the team.

There’s Always a Team Theme, Why Not Take a Themed Tour Too?

 Holidays are as old as civilization itself and whether your team is full of Spooky Season lovers or Jolly Elves, there’s a tour in the city for you! 

Get ready to quake in your boots on Bobby’s Fright Hike – Halloween edition bike tour.  You’ll bike around some of Chicago’s most famous spots while learning of the hauntings at sites such as the ever haunted Congress Plaza hotel and the John Hancock Center. Nothing quite builds team morale as living through something scary together, and a team themed costume certainly counts as such! Come dressed up, if you dare. 

If your group is looking to experience some good ol’ fashioned winter holiday team building, then look no further than Bobby’s Holiday Hike. This three-hour food and walking tour mixes classic Chicago foods with the merriment of the season. 

This is a great option for changing up the usual holiday office party and taking the team building outside to the streets of Chicago!

Visit The Christkindl Market Together

Christmas Markets started to make their appearance during the mid-16th hundreds in Nuremberg, Germany, but have become a world-wide holiday favorite. The Christkindl Market here in Chicago has been in operation since 1996 and has made its home at Daley Plaza since 1997.  

Nothing provides a team with more opportunities to bond than picking out a Secret Santa gift for their co-workers, or an ornament to go on the office tree. Go shopping for handcrafted trinkets and other artisan products from Germany. Join in Chicago’s favorite Christkindl tradition and pick out which souvenir mug will hold your hot cider, hot coco, or hot mulled wine. 

Only so many guests can grace the market at once so plan for long lines to gain entrance on nights and weekends. The good news is that those lines usually move fairly fast and mulled wine can fix most grievances. The Market opens in Mid-November and goes until December 24th.

Need a Winter Team Building Idea? See How the Group Does Ice-Skating

That’s right! Rockefeller Plaza isn’t the only city ice skating rink here in the United States.  Chicago operates The McCormick Tribune skating rink in Millennium Park, which is Chicago’s number one visited tourist attraction, gathering over 5 million people every year. Since its opening in 2001, three years before Millennium Park would open in 2004, the McCormick Tribune Skating Rink has become one of Chicago’s favorite Winter traditions.

See who can skate the longest without falling, or who can skate backwards the best! Take a group photo out on the ice with the city and holiday lights gleaming in the iconic background “Cloudgate” or as it’s more commonly known “The Bean.”  

When you’re done, head over to Momentum Coffee Millennium Park, located in the building underneath “The Bean” to grab a hot coffee or hot chocolate to celebrate your team’s ice-skating prowess.  Tickets are free, but online reservations are required to skate. 

Head back to Maggie Daley Park, located just east of Millennium Park to check out their Skating Ribbon. A great addition or substitution to the rink, the Ribbon winds through towering climbing walls and is lined with ever-green trees, solidifying the Winter Wonderland theme. 

The ice-skating rink and Skating Ribbon are open from November to March. Tickets range between $15-$25 depending on the day and time you are booking your tickets for. Walk up tickets are available but are cheaper to purchase online beforehand.

A City History Built On Teamwork — We Understand the Importance of Team Building, and Fun Activities To Do So!

Chicago’s very essence is a legacy of teamwork, dedication, and passion. We are a second city built on the ashes of our predecessors, shaped by fire and water. The innovation of the Skyscraper, the successful implementation of the grid system after the city’s destruction, and the monumental environmental clean-up of the Chicago River and Lake Michigan all point to dedicated teams working together to achieve feats men only ever dared to dream of before.  

There truly is no better place to inspire your team and ignite a drive to work together than Chicago. Let us help you organize your corporate group outing and team building activities with a walking or biking food tour and we promise to show you some of the best things this city has to offer.