Three Tips for Planning a Chicago Family Reunion

Planning a Chicago family reunion can be tricky.  With multiple days, multiple age groups, and multiple guests with multiple opinions. At Chicago Detours, we’ve arranged many a Chicago family reunion. We’d like to share with you a little of the knowledge we’ve learned. Here are three tips that will help you plan a memorable Chicago family reunion.

We research ideas about how to experience Chicago history, architecture and culture like this while developing our live virtual tours, in-person private tours, and custom content for corporate events. You can join us to experience Chicago’s stories in-person or online. We can also create custom tours and original content about this Chicago topic and countless others.

Tips for planning a Chicago family reunion
A family reunion with 109 guests on our Jazz, Blues and Beyond Tour last summer. Photo by Amanda Scotese.

1. Keep things interactive.

Activities like tours and games help relatives become friends. After all, just because you’re related doesn’t mean you know each other. And, for those family members who wished they didn’t know each other, it can neutralize tense interactions. 

Bowling, axe throwing, or whirlyball can be fun for any age. Learning together can also be a great bonding experience. Think outside the typical family reunion box and consider options that are usually classified as corporate outings. For example, take a cooking class together. We’ve got more possibilities right here, including joining us for a tour.

Our tours are a great way to learn and interact as a group. Not to mention we take care of a lot of the planning for you. Guests on our custom neighborhood tours visit Chicago neighborhoods north to south while learning about Chicago’s rich music history from an animated guide. To top it off, we an arrange for a blues musician to give everyone a harmonica lesson (with a harmonica courtesy of Chicago Detours) and an exclusive live performance.

“Myself and my family had an amazing time on the tour! Amanda was great and the planning process was a breeze. Honestly, it was the highlight of our family reunion,” previous private tour client Pam Euring said.

Tips for Planning a Chicago family reunion Ukrainian Museum
Not all venues, like the Ukrainian National Museum, advertise they are available for private events, so be sure to call. Photo courtesy of the Ukrainian National Museum.

2. A banquet hall can turn your Chicago family reunion into a cultural experience.

Make your family reunion in Chicago even richer by hosting it in a cultural institution. Why not connect with your own shared cultural identity or celebrate a new one? Possibilities include the Ukrainian National Museum in Ukrainian Village or The National Museum of Puerto Rican Arts and Culture in Humboldt Park. The Chicago Cultural Alliance is a great place to start planning your family reunion in Chicago. 

You could also plan a dinner in an architecturally significant space. Venues like The Keith House on Prairie Avenue or SR Crown Hall at the Illinois Institute of Technology are picturesque and unexpected. Take it from us, architecture is a great conversation starter and can make a good time truly memorable. 

Tips for planning a Chicago family reunion
In addition to The Chicago History Museum, Old Town is also home to The Second City, a lot of shopping and plenty of great restaurants. Photo by Alex Bean.

3. Let your fam make their own Chicago adventure.

Up to this point I have failed to directly address one of the biggest challenges facing any Chicago family reunion. Teenagers. What do they want? What kind of family reunion activity would they think is cool and fun? Probably nothing, right? Right. Lean in and allow the dreaded teens (and the rest of your family) choose how to spend their time, within reason.

I’d recommend unleashing your teens on one of the many cool neighborhoods outside downtown. These small neighborhoods in Chicago are perfect for allowing folks to explore shared interests or follow the beat of their own drum. Your relatives, teenage or not, can shop, eat, learn and explore on their own in densely packed neighborhoods like Old Town and Lincoln Square. They’ve got their freedom and you’ve got a nice spot to window shop or chill out over coffee. No one under the age of 18 can say you’re uncool for planning it, because they made all their own choices. So there. 

– Morgan Lott, Private Tour Coordinator and Tour Guide


Chicago Detours is a boutique tour company passionate about connecting people to places and each other through the power of storytelling. We bring curious people to explore, learn and interact with Chicago’s history, architecture and culture through in-person private group tourscontent production, and virtual tours.


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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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