Five Creative Ideas for a Chicago Girlfriends Getaway

A girlfriends getaway to Chicago is not foreign here at Chicago Detours. We are a female-owned and operated business. We know all about the importance of a good #girlsquad and a good girlfriends getaway. The best part of being in a girl squad, of course, is that they make the best travel companions. Who better to explore new places with than your very best girl friends?

The Bean, the SkyDeck and the Art Institute are easy ideas for a fun Chicago girlfriends getaway. But what about if your lady group wants a less touristy experience? Well, we can create custom tour for your private groups, of course.

The Areas of our #GirlSquad Expertise

As a tour guide, I noticed lots of girlfriend groups coming to us at Chicago Detours on a ladies weekend getaway to Chicago. They tend to be girls groups that love learning about architecture and history. We get lady groups doing a landmark birthday trip (like 30th or 40th birthday) or bachelorette party groups.

Here at Chicago Detours, we share the Chicago stories and places even locals don’t know. So for all those #girlsquads out there looking for a more off-the-beaten-path girls weekend, here are some fun ideas for a girlfriends getaway in Chicago.

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.

Brunch with your Girlfriends Group at Three Arts Club

Chicago Brunch Location at Restoration Hardware 3 Arts Cafe
Photo by Lou Stejskal via flickr.

The first time I came with a group of girlfriends to this Gold Coast restaurant, I was blown away! Three Arts Club Cafe is one of the most aesthetically pleasing restaurants imaginable by virtue of it sharing the space with the super-chic furniture store Restoration Hardware. The gorgeous architecture and delicious food are both perfect for photo opportunities.

The building is also super historic. Dining here with your girlfriends provides a great connection to women’s history! The Byzantine-inspired building was designed by Holabird and Roche in 1915. It originally hosted a women’s club of the same name. This ladies group provided housing and community for female creators of music, painting and drama. Some of Chicago’s most prominent women were members of the Three Arts Club, including Jane Addams and Constance McCormick. These girlfriends most surely enjoyed a fine ladies lunch here!

So if you and your girlfriends love good food, Instagrammable venues, and some Chicago history, too, you may want to consider Three Arts Club Cafe for the itinerary of your girls getaway to Chicago.

Spend an Afternoon with the Girls at the Museum of Contemporary Art

group visit to the museum of contemporary art MCA
Photo by Phil Roeder via flickr.

Take your girlfriends on a getaway off the Magnificent Mile at the Museum of Contemporary Art. Located a short walk away from Water Tower Place, this sophisticated haven includes more than 2,500 artworks. Its permanent collection spans media and movements from the 1920s to the present. With a coterie of revolving installations and exhibitions highlighting the most exciting movers and shakers of the contemporary art world, your girlfriends may carve out a favorite area of the museum for your Chicago getaway weekend.

Personally, I love meeting my girlfriends at the MCA for Tuesday on the Terrace. We enjoy a free showcasing of local jazz talent while sampling beverages and delicious apps from their cash bar.

Visit Koval Distillery on Your Chicago Girlfriends Getaway

Girlfriends Weekend Getaway Group visit at Koval distillery

If your girlfriends aren’t the “rosé-all-day” types, you could take you girlfriends group to one of the 167 breweries in Chicago for your getaway. Or you and your lady friends could get a little more adventurous with a visit to the first distillery to open in the city since the 1800s. KOVAL Distillery produces organic whiskey, liqueurs and specialty spirits in their still in the oh-so-atmospheric neighborhood of Ravenswood, which is north of downtown Chicago. In addition to taking a quick look in the shop, you could consider KOVAL’s scheduled classes and tours with tasting that are bookable through their website.

Your girl group can either sign up on their website or arrange a private tour for a special event. All tours have a KOVAL employee lead discussion on the differences between white and aged whiskey, the distillation process, and show attendees where each and every step of their small-batch spirit production process takes place. Tasting of numerous spirits is just one of the many perks on this tour! The bottles have quite and impressive design and would be gorgeous souvenirs for your girlfriends Chicago getaway.

Make a Custom Handbag for your Girlfriends Getaway

creative ideas for girlfriend getaway group in chicago laudi vidni
Laudi Vidni, in Lincoln Park, offers custom accoutrements – perfect memento for a Chicago girlfriend getaway. Photo courtesy of Laudi Vidni.

While a laser print shirt may be fun, we have a special idea for your girls getaway weekend in Chicago. You can arrange a truly custom experience for your girls weekend and head to Laudi Vidni on Armitage Avenue in Lincoln Park. The store was actually founded by girlfriends Laura Kofoid and Grace Tsao-Wu, Laudi Vidni. Here you and your girlfriends get the unique chance to fully customize quality leather goods. The handbag and padfolios are made from their extensive catalog of fine materials, linings, and details. Items are then handcrafted in Chicago and sent anywhere in the United States with a two-week turnaround time.

And so what does this mean for your girlfriends getaway? Laudi Vidni welcomes special group events to their design space. Private groups can check-out their materials, mix and match, and get advice from expert stylist advice exclusive to your event. You walk away with a stylish, practical memento of your weekend in Chicago with your girlfriends, and you’ll make memories while you create it.

A Custom Private Tour from Chicago Detours

bar tour beer glass
Raise a glass with your gals on our Historic Chicago Walking Bar Tour. Photo by Pawel Skrabacz

(Learn more about why we switched to offering Virtual Events in 2020.)

As a guide for the old Historic Chicago Walking Bar Tour, especially in the summertime, I seemed to host girls getaways almost every week! And really, it’s no surprise.

With a fun and engaging tour guide to facilitate (ahem), this 2.5-hour long tour explores Chicago’s River North neighborhood. All your girlfriends will get food and drink along the way. You and your ladies will get to enter inside some of our favorite drinking spots near the Magnificent Mile. Private groups on this walking tour get to eat, drink and learn about the city’s entertainment history and architecture.

Girls getaway groups particularly love enjoying a glass of wine or beer amid the ambiance of a historic 19th century mansion at the SideDoor. This restaurant is inside Lawry’s the Prime Rib, which has called this Gilded Age building home for decades. It is one of the stops on this historic tipsy trek. For a pro-tip, I recommend you snag a picture of the original chandelier, sold to Lawry’s from the McCormick Estate.

To further ease your event planning for your girlfriends getaway in Chicago, you can upgrade the Historic Chicago Walking Bar Tour to include a full meal. No more guesswork for where to have dinner or confusion over paying the bill! Inquire about availability and pricing on our Private Group Tours page.

Hopefully this guide has some fun ideas that will help you plan a girlfriends getaway to Chicago. Whether it’s a landmark birthday like a friend’s 30th, 40th, or 50th birthday or perhaps a bachelorette party, we are sure Chicago will be an excellent destination for your girlfriends getaway weekend.

– Ellen Bushong, Private Tour Coordinator and Tour Guide


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.


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



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

Book a chicago event

Let’s Connect!