Planning memorable team building events in Chicago can be tricky. You want to please everyone, and facilitate genuine bonding time between coworkers. Obviously, we highly recommend a bike, walking, or food tour with Bobby’s Bike Hike. There’s no better way to get the team active and out and about in the city than on one of our top-rated guided tours. But there’s so much more out there! Below is how Bobby’s Bike Hike gets the team together— five fun and unique camaraderie-boosting activities to take the guesswork out of your planning. As always, let us be your guides!

Second City Improv Comedy Show
Improvised comedy, aka comedy that happens on the spot, was invented in Chicago and perfected on the Second City stage, which opened in 1959. Second City offers shows nightly, all hilarious, at various price rates, and has an in-house bar-restaurant. Mainstage shows can accommodate big groups, smaller upstairs theatres offer a more intimate setting. Audience participation, in-the-moment inside jokes, and a totally relaxed atmosphere make this the perfect place for your team to let loose and laugh together.

Best Time of Year: While Second City rolls out hilarity all year long, this is a great winter pick because of its indoor status.

Beermiscuous Friday Afternoons
Beermiscuous boasts itself as “a coffee shop for beer,” meaning it combines the cozy and zen vibes of your local coffee shop with dozens of interesting beers on tap and in the cooler. Fun custom team building activity idea: have the whole staff work from Beermiscuous on a Friday afternoon. This corporate team building event is obviously better for smaller staffs, and is optimal for a time period that your organization boasts a lighter workload. The staff brings laptops, and you all answer emails while sipping local craft brews! Then when five o’clock rolls around, coworkers are welcome to hang around for more, or travel as a group to one of the many breweries sampled.

Best Time of Year: Chilly fall days, or rainy spring afternoons!

The Chopping Block Cooking Classes
Nothing gets a team working together quite like getting them in the kitchen. The Chopping Block, which has locations in Lincoln Square and the Merchandise Mart, leads a myriad of different cooking classes to organically build relationships over food. The team will gain fresh new skills to take home with them, and get to share a meal together when it’s done. The Chopping Block can accommodate anywhere from 6 to 300 people, making it the perfect Chicago corporate team building activity for groups of any size.

 Best Time of Year: We recommend it in January. Not only will the fun event stave off the winter blues, but it offers team members new skills to follow through with New Year’s’ resolutions.

Murphy’s Rooftop Viewing – Chicago Cubs
We at Bobby’s Bike Hike think you’d be hard-pressed to find a more loyal fan base than the movement behind the Chicago Cubs. Cubs history is woven into the fabric of our city, and bringing your group out to enjoy a game is engaging them with the very pulse of Chicago. But don’t settle for mediocre seats with no perks! Book a game with Murphy’s Rooftops. Run by the team at Murphy’s Bleachers, (one of the most famous Wrigleyville watering holes) Murphy’s Rooftops offers the best Cubs rooftop experience available. Food and bottle service can be guaranteed, even when a Cubs win cannot.

 Best Time of Year: Baseball, season of course! For best options in availability and to reward your hard working team, try a weekday game!

Trivia and Game Nights – Local Bars and Restaurants
There’s no better way to breed a little bit of healthy competition among your staff than with bar trivia. The events are usually free, your group just covers food and drink, and these can be an amazing way to bond. If you have a small organization, you all can be on the same team and crush the outside competition! If you have a big group, you can shake things up and organize teams by department, or by coworkers who don’t know each other as well. There are a number of ways this can benefit group morale. Some of our favorites around Chicago include PBR Bingo at Boiler Room in Logan Square, the Buzzed Spelling Bee at Elbo Room in Lakeview, and Movieoke (yes, you read the lines from famous flicks) at The Whistler, also in Logan Square.

Best Time of Year: Whenever your team is feeling smart!

What are some of your favorite corporate outings in Chicago? We’d love to hear them all! Shoot us an email, Instagram message, or Facebook message so we can show all of the awesome activities some love!