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March 2020

Chicago Corporate Events: 21+ Fun and Unique Ideas That Will Blow Your Team Away

navy pier best restaurants
Photo Source: Chicago Food Planet

Chicago Corporate Events: Best 21+ Ideas That Will Blow Your Team Away

We all know that corporate life can be fast-paced, high-stakes, and ever-changing. It’s one of the reasons why employees work so hard—and deserve to party hard, too. The problem is that too many companies resort to the same old cheese-plate-and-open-bar scenario instead of finding an activity that actually leaves their team recharged and ready to roll.

It doesn’t have to be that way, though.

Chicago is host to some of the most unique, whimsical, entertaining, and legit fun Chicago corporate events this side of the boardroom. In this guide, you can find the perfect celebration for your company, whether it’s a small startup of five folks or a Fortune 500 company made up of 5,000. Here are 21+ unique and fun Chicago corporate event ideas that will blow your team away.

Come Rain or Shine: Fun Chicago Corporate Events for All Seasons

Your team works for you 365 days a year. There’s no reason you can’t show your gratitude at any point during that time. Whether you’re kicking off the fall, offering an escape from the winter blues, celebrating the first signs of spring, or finally enjoying the summer sun, these events will keep everyone happy and humming.

#1 Turn Your Lunch Hour into a Feast with a Chicago Food Tour

Deep dish pizza chicago

Photo Source: Chicago Food Planet

Be gone, sad sandwich platter! A food tour of Chicago is a fantastic way to get your co-workers fed, festive and full of new friends. Along the way, our expert guides share insider knowledge of Chicago and its famed culinary scene.

Got some green newbies? Introduce those Chicago transplants to the legendary Lou Malnati’s, sample a delicious Al's Beef sandwich and the famed Portillo’s on Iconic Foods of Chicago Food Tour. You’ll stroll Michigan Avenue and the Magnificent Mile, snapping group photos in front of the landmarks like the Wrigley Building and the Chicago Water Tower.

It gets better:

Experiences can be customized to suit the needs and preferences of your team so everyone has a fabulous experience. Our corporate events team will be available every step of the way too, assuring the event goes off without a hitch.  

Insider Tip: Hungry for more? Foodies will appreciate our guide to the 20+ signature dishes in Chicago where you’ll find old standbys like deep dish and new favorites like apple candy balloons.

#2 Take Big Risks at Casino Night

Chicago poker activities

Photo Source: US Poker & Casino Parties

For the company that puts it all on the line, Casino Night may be just the kind of memorable night out they need. US Poker & Casino Parties specializes in corporate parties, fundraisers, and other events, assisting customers each step of the way.

With games like Texas Hold ‘Em Poker, Blackjack, Roulette, and more, you’ll get the thrills of a dazzling evening in Vegas with none of the regret.

#3 Bounce Ideas off Each Other at AceBounce

Chicago ping pong ace bounce

Photo Source: @acebounce

The only place where a constant back-and-forth is a good thing?

A ping-pong bar!

AceBounce offers all the fun vibes of your parents’ rec room but in an upscale environment, with the additional bonus of having a DJ and a mixology program to keep the party going. Games Gurus are also there to entertain guests with unique ping-pong games designed specifically for groups, regardless of ability.

#4 Play Hard in the Loop—the West Loop

Chicago West Loop Neighborhood Attractions

Photo Source: Chicago Food Planet

Mere minutes from Chicago’s business district, the West Loop is one of the hottest food destinations in the country. Chicago Food Planet’s Gateway to the West Loop Food Tour will give your team a behind-the-scenes look at the city’s culinary revolution while they eat their way through famous restaurants, hidden gems, and artisan eateries, including Bonci's Pizza, Cemitas Puebla and Kuma's Corner. This option is awesome any time of the year, but it really shines during the summer, when the trendy West Loop streets come alive with local revelers and fashionable visitors alike.

Insider Tip: Chicago summers are the absolute best thing about Chicago winters: they’re the only reason locals tolerate the harsh weather. For a guide to making the season perfect, check out our 18+ recommended activities for the summer.

#5 Suss Out the Competition at Game Night Out

Chicago game night

Photo Source: Game Night Out

Forget Monopoly, Risk, and Clue. For a truly unforgettable game night out with colleagues, look no further than Game Night Out. This completely private experience provides two jam-packed hours of original party games that will keep everyone moving, challenged, and ready to show their skills.

It’s a great option for small companies, since each event is capped at 24 people.

#6 Demonstrate Your Drive at K1Speed

Chicago go karting

Photo Source: @k1speed

Start your engines and blow off some steam with an outing to K1Speed, Chicagoland’s premiere indoor karting complex. Both the Addison and Buffalo Grove locations offer two challenging tracks, nightclub-style outing, an on-site restaurant, and meeting room with AV connections. K1 Speed makes sure you race only with the members of your group for a truly bonding experience.

#7 Find a Better Use for a Projector with a Movie Outing

chicago corporate events

Photo Source: Chicago Review of Books

Big-budget blockbusters, Hollywood classics, the latest indie flick—whatever your team is into, there is a Chicagoland theater willing to rent out their space so you can enjoy it together. AMC Theaters may be the most obvious choice for corporate outings, given their size and selection, but don’t snooze on the smaller venues.

Places like the Logan Theater in Logan Square, the Davis Theater in Lincoln Square, and the Music Box in Southport are also happy to host groups that may want a more intimate, quaint space.

#8 Enjoy the Best Views Navy Pier has to offer at Offshore Rooftop

navy pier chicago centennial ferris wheel

Photo Source: Navy Pier

Offshore Rooftop is somehow both lively and yet incredibly serene. 

Navy Pier's amazing restaurant and event space boasts the best views in all of Chicago.  Technically, it's also the world's largest rooftop.  The space has flexibility and can easily accommodate both indoor and outdoor events.

Come for the vibes.  Stay for the view.

#9 Score Some Major Points with the Boss at Headquarters

corporate events chicago

Photo Source: Headquarters

Trade the great game of business for the low-key joys of arcade games at Headquarters.

Have a large group to entertain and please?

This massive River North complex includes over 65 arcade games and pinball machines, a rotating selection of draft and canned beer, a delish menu of favorite grub-pub items, and several areas that can be rented out exclusively to your group.

#10 Break Confidentiality Agreements at Safehouse

chicago team building ideas

Photo Source: Safehouse

There’s no need to dabble into corporate espionage and intrigue when you have Safehouse.

The #1 spy-themed restaurant and bar in Chicago provides an interactive experience for groups of up to 300 people. Combining games, technology and challenges, this is one outing that will put the busybodies in the office to good work.

#11 Do Business on the Golf Course at Topgolf in Chicago

chicago group activities

Photo Source: Topgolf

If you dream of closing the deal with golf club in hand, you don’t have to wait for the warm weather to hit.

All three of Topgolf’s Chicagoland locations come equipped with climate-control hitting bays, a rooftop terrace with fire pits, and indoor meeting rooms for your team.

#12 Unleash Your Creativity with Native 312

chicago corporate workshops

Photo Source: Native 312

Loosen up that tie, roll up your permanent-press sleeves, and get your hands dirty with Native 312. This isn’t your stuffy VP’s paint party. Instead of brushes and watercolors, guests are armed with spray paint and a full-on wall to express themselves.

It gets better:

Local artists guide each workshop and their staff can also help you with venue, bar packages, and entertainment options.

#13 Witness the Power of Teamwork at Second City

chicago second city theater

Photo Source: Group Fox

Improv is an art form that fosters collaboration, trust, and quick thinking. It is also laugh-out-loud funny! And there is no better place to see improv than at legendary comedy institution, Second City. Invite your co-workers to eat drink, and see the future Tina Feys, Steve Carrels, and Bill Murrays—all alumni of this famed theater.

But wait, there’s more:

Second City can also be hired to perform at conference excursions, fundraisers, donor appreciation events, and conferences. Want to try it out for yourself? Their team also provides workshops and team-building exercises to corporations.

Hot Activities for Your Rays of Sunshine: Best Chicago Corporate Summer Events

Once the warm weather hits, nothing will show your staff that you appreciate them like a much-needed break from the office. Chicago is a fantastic place to soak up the sun, live up the long days and freshen up that annual summer outing.

#14 Make 2020’s Company Picnic a Walk in the Park

chicago corporate picnics

Photo Source: Windy City Fieldhouse

Windy City Fieldhouse is here to throw the picnic of your dreams with none of the hassle. They’ll take care of finding the ideal location, the best catering, and even transportation—so all you and your staff have to worry about is remembering the sunscreen.

Depending on your needs and interests, they can also organize softball tournaments, team challenges, Chicago scavenger hunts, relays and other games to keep everyone entertained.

#15 Smooth Sailings Deserve to Be Recognized on the Spirit of Chicago

chicago corporate outings spirit of chicago

Photo Source: Spirit of Chicago

Show your team their hard work paid off with a dazzling evening on the water.

Spirit of Chicago cruises will welcome your team aboard on one of their sleek fleets, where they can party the night away on their decks. If the mesmerizing Chicago skyline isn’t enough, passengers can also enjoy foosball, shuffleboard, casino games and more on the ships.

#16 Cover All Your Bases at Wrigleyville Rooftops

chicago wrigleyville rooftop corporate party

Photo Source: Wrigleyville Rooftops

Catching a baseball game at Wrigley Field may be a storied Chicago summer tradition, but how can you make sure even the sports-averse have a good time?


Turn to Wrigleyville Rooftops. Each one of their eleven rooftops will give your group spectacular views of the field—or the city, if that’s more your speed.

That’s not all.

Food and drinks are included so even White Sox fans will be happy with the spot. There are also meeting rooms with state-of-the-art equipment for any pregame presentations.

Cool Ideas for Chill Times: Best Corporate Winter Events

Looking to celebrate the end of a fantastic year?

Top off those last quarter wins with holiday parties, festive activities, and spectacular celebrations that will warm the hearts of your entire team.

#17 Throw a Throwback Corporate Holiday Party in Chicago at Bordel

team building corporate chicago event ideas

Photo Source: Bordel

Step into Wicker Park’s lux speakeasy Bordel and be immediately transported to a time when the cocktails were classy, the jazz was smoking, and velvet seating was all the rage.

The swank and seductive space is ideal for any corporate holiday party that wants a touch of naughty to reward all those who have been nice.

#18 Strike! Strike! Strike! with Bowling Night

chicago bowling events

Photo Source: Lucky Strike

Looking for some good, old-fashioned, wholesome fun?

Then lace up those bowling shoes and get swinging at Lucky Strike. In addition to eighteen bowling lanes, the Streeterville venue also features ping-pong tables, billiards, arcade games, and a full service bar and restaurant.

There’s even WiFi for those truly committed to refreshing their inbox every five minutes.

#19 Plan an Outdoor-ish Retreat Right in the City with Park & Field

chicago corporate restaurant outings

Photo Source: Park & Field

Does your team love the idea of being outdoorsy but hate the actual outdoors? Logan Square’s Park & Field, an exquisitely decorated vintage sports bar with an ultra hip vibe, is the solution. Your co-workers will get to indulge in their unique cocktails, nosh on their locally-sourced bar bites, and live out their woodsman fantasies right in the city.

This is the best part:

Park & Field has an amazing 6,000 square foot patio with bocce courts, fire pits, and an outdoor camper bar that is open year-round. During the winter months, they provide guests with piping-hot beverages, fresh-out-of-the-oven cookies and DIY s’more kits.

#20 Cutting-Edge Chicago Corporate Holiday Ideas at the Museum of Surgical Science

chicago networking ideas

Photo Source: Science News

Companies that thrive on the quirky, the kooky and the downright creepy (you do you) will want to celebrate their own uniqueness at the Museum of Surgical Science. All joking aside, this may be one of the most heart-stopping event spaces in Chicago.

Its opulent building and breathtaking views will turn any evening into a sophisticated affair.

And yes, you can also satisfy your morbid curiosity by checking out exhibits like “A History of Blood Transfusion” and “Dental Office: A Checkup On Dental History.”

#21 Sweep Your Problems Aside at Kaiser Tiger

chicago curling ideas

Photo Source: @kaiser_tiger_chicago

Two words: Ice. Curling. Yes, you and your colleagues can try out this most intriguing, enigmatic and Canadian of sports at Kaiser Tiger.

The friendly West Loop bar has three ice curling lanes in their beer garden during the winter months that will amp up the fun of any corporate event. Jenga, bags, and an assortment of mouthwatering bratwurst will entertain you while you wait your turn.

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