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A Good Time Had By All


Exclusive group experiences to elevate your corporate event

There’s something about a fun-filled, unique activity that transforms an event into an unforgettable experience that people will delight in long after it’s over. When you book with us, you can take advantage of our exclusive partnerships to elevate your corporate off-site—or any occasion that brings your group to downtown Chicago. If that occasion is a social event or wedding, we have offerings just for you too.

At The Gray, our team excels at planning all types of events. Below we’ve highlighted a selection of the corporate offerings—from crafts and culinary arts to wellness classes and team-building workshops with a twist—that you can add on to your event, whether you’re staying with us for business or pleasure.

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Corporate Events

empanada food plate

Empanada Making Class

These crowd-favorite savory pastries are staples in South America for good reason—they’re delicious. And what brings people together more than preparing and enjoying delicious food as a group? Let’s gather your team for our empanada-making class with our Chef de cuisine from Boleo. Together we’ll make dough, conduct various empanada folds, prepare the fillings and dig in!


Stir It Up

There’s something inspiring about teamwork in action, and we can’t think of a team that works better together than wine and cheese. Collaborate with our Sommelier to guide you through an informative tasting or Head Bartender to engage in the art of making a good old fashioned. Stir up these options at your next event at Vol. 39 and impress your guests with a reimagining of a crowd favorite.

Boleo Bungalow

Boleo Bungalow

Nothing says spring like a private oasis right at your fingertips. Consider transforming Boleo’s Rooftop at The Gray into a space with stunning sheer canopies, greenery and bohemian accents provided by CSI DMC. Top it all off with mobile champagne carts and lush lounge groupings for guests to unwind and enjoy.


Private Trolley Tours + Executive Buses

Chicago is a city that was made to be explored—from our bustling downtown to our vibrant neighborhoods, each with their own identity and culture to discover. Thanks to Signature Transportation, your group can enjoy a private 30-passenger trolley experience that includes rear porches or, if you’re venturing a bit further, the fleet of Executive Buses accommodates between 24 and 43 guests.

Gray Theory

Kick off your meeting with an adrenaline-pumping workout on-site! CSI DMC will bring in a renowned Chicago boot camp instructor for a full body experience. Throughout the meeting space, various stations will challenge your guests both mentally and physically. Get ready to set the 'tone' for your day!


River to Rooftop

For groups small and large, consider giving guests the most iconic look of Chicago. CSI DMC will transport guests through the river for a private architectural boat tour, ending through the locks at Navy Pier where they will be escorted to a rooftop dinner. See Chicago from all points of view! 

empanada food plate

Artistic Endeavors with Emmy Star Brown

Add a creative activity to your next corporate event, paint customized murals and unique artistic gift with the help of Chicago-based artist (and our creative partner) Emmy Star Brown.


“Fore” the Win

Want to work on your swing in between your meetings? We’re game! Let’s have fun with it and give you a worthy break. Put your green jackets on and get in some putting action on our various greens paired with a 10.5’ simulator screen.

Happy Tails

Happy Tails

Who doesn't love puppy therapy? CSI DMC can organize a variety of giveback activities including hosting a shelter on-site where all guests can take a break from their all-day meeting and interact with dogs from a local shelter in a custom play pen on-site.

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