Six New Ideas for Chicago Corporate Outings

Let’s imagine it’s the moment when you decide it’s time to change up your typical Chicago corporate outing. It is a regular Thursday. You could be eating yet another catered lunch at your desk. You could be standing around at a happy hour at the bar around the corner from the office. Or maybe you’re listening to yet another motivational speaker and feeling less than motivated. In any case, you’re bored at a corporate work event. It is time to spice things up with some fresh ideas for Chicago corporate outings. We have six suggestions to fit any workplace that needs an energy shake up.

We research Chicago history and architecture like this while developing our live virtual events and custom corporate events. Join us for our public virtual events or book an exclusive team-building event for your private group. We can also create custom tours and original content creation about this Chicago topic and countless others.

Fresh Ideas For Chicago Corporate Outings
Photo courtesy of Backyard Axe Throwing League

Corporate Outing Idea #1: Relieve Tension with Axe Throwing

Instead of sending (another?) passive aggressive email, throw an axe instead. At Backyard Axe Throwing League, colleagues can relieve stress productively in a safe space with talented instructors. One big bonus is that it currently costs less than competitor Bad Axe Throwing. No alcohol allowed near the axes at this spot, so it is ideal for teetotaling corporate outings. You are welcome to bring outside food and non-booze beverages, though, making your event a complete evening in one location. BATL describes their facilities as “a cross between a battle cage and a bowling alley”. Along with tunes courtesy of BATL and friendly competition courtesy of an organized tournament for participants, what’s not to love?

Corporate Outings Idea #2: Cook and Sing Together

At Korean barbecue hotspot BellyQ, cook and eat together and even provide your own entertainment in the form of karaoke tunes. Ideal for an office full of independent spirits, at BellyQ you can book private rooms. Stocked with a full bar, the karaoke part of the evening, on top of the delicious eats, will certainly make some memories.  

Corporate Outings Idea #3: Compete Over Cake 

At the renowned culinary institution of Kendall College, they offer corporate events where teams construct and decorate a cake. They call this corporate outing “Let Them Eat Cake.” Particpants are set-up for success with instruction from a professional, trained chef in one of the school’s professional kitchens, along with support from Kendall College students. The chef then judges the teams based on their cake and presentation, maybe there’s a prize, and then you eat the cake. Coworkers can tap into a competitive side with a sprinkle of creativity, making “Let Them Eat Cake” a super cool corporate outing for building interpersonal connections. Kendall College is located on Goose Island on the river, super close to downtown offices. 

Medieval Times Fresh Ideas for Chicago Corporate Outings
Photo courtesy of Medieval Times

Corporate Outings Idea #4: Indulge in Kitschy Nostalgia

Is Game of Thrones is all anybody talks about around the water cooler? Or do your corporate staff meetings ever resemble GoT combat? At Medieval Times  in Schaumburg, you can get dinner and indulge in a little childhood nostalgia with the entertainment. Some may even enjoy a little violent catharsis. Make it happen by booking a private bus, or even a party bus, and make it a fun field trip to the burbs. The Chicago Castle offers special benefits for private corporate groups.

Corporate Outings Idea #5: Laugh with Chicago Improv  

You live in Chicago. And if you haven’t attended an improv show or workshop, I’m not convinced you really live in Chicago. Improv is historic to Chicago, it was born here! For a corporate outing in Chicago, this critical Chicago bucket list item. With iO Theater you can bring your corporate team for a private performance or a workshop designed especially to teach these skills for Chicago corporate outings.  

Fresh Ideas For Chicago Corporate Outings
Guests enjoying stories, food on our Old Polonia and Wicker Park Tour. Photo by Pawel Skrabacz

Corporate Outings Idea #6: Tour Chicago History

Look, obviously there was no way we weren’t going to suggest a private group tour with Chicago Detours. We work with a variety of companies, from small to big and from law firms to tech start-ups. We’ve got walking tours and bus tours, with or without dinner and/or drinks. You can charter a private yacht for a Chicago architectural boat cruise as well. Our historic bar tours were most popular for corporate outings. Our “Historic Chicago Walking Bar Tour” started right at the Michigan Ave. bridge, walking distance to many downtown offices. For “Big Shoulders Historic Bar and Food Tour by Bus” we picked you up your office and whisk your corporate team off to explore historic bars in the very historic Bridgeport neighborhood.  

— Morgan Lott, Private Tour Coordinator


In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore, learn and interact about Chicago’s history, architecture and culture through custom tours, content production, and virtual events.


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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