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10 Chicago Hidden Gems to Explore!

Oct 9, 2020

10 Chicago Hidden Gems to Explore This Fall | Thank You For The Best Year Yet

(Above: Taken in Humboldt Park, one of my favorite places. This is not in fact a “Hidden” gem, so good thing Jessica is here to share 10 REAL hidden gems!) 


I could think of nothing better to kick off your weekend plans than to hand over today’s post to local Chicago writer, author, and GG reader, Jessica Mlinaric. 

Jessica recently released her book, Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and she so generously sent me a copy. As soon as I started flipping through it, I said, “I HAVE GOT TO HAVE HER WRITE A BLOG POST!” and, luckily for us, she enthusiastically accepted! 

Her book is SO cool and filled with amazing recommendations I’ve never heard of–and I’ve lived in Chicago for over a decade now! It would also make a really amazing gift for any Chicago lover, or newbie to Chicago! (Plus, you’d be supporting a fellow female biz owner at the same time!) 

Now, I shall pass the torch to Jessica to share her 10 amazing secret spots with us! 

10 Chicago Hidden Gems to Explore This Fall


Hi all! I’m Jessica, and I’m so excited that Jess invited me to share some fall inspiration with you today. I’ve spent a lot of time digging into Chicago’s surprising sites and unique activities. While our travel plans are limited this year, you can still find the thrill of discovery that we love about travel by uncovering a hidden gem close to home. Here are 10 ideas for exploring some of Chicago’s secret spots this fall. 


10 Chicago Hidden Gems to Explore This Fall!


Enjoy Fresh Air at the North Park Village Nature Center

10 Chicago Hidden Gems to Explore This Fall

One upside of this pandemic is that it has encouraged me to seek out Chicago’s natural areas. This 46-acre urban oasis in North Park offers a stroll through wetland, forest, prairie, and savanna settings. You almost can’t tell that the area was once home to a tuberculosis sanitarium! From 1915 to the 1970s, this was the site of Chicago’s Municipal Tuberculosis Sanitarium. The natural setting was restful for recovering patients, and still offers an escape from the bustle of the city today.

Get Outfitted for Halloween at Woolly Mammoth Antiques and Oddities

10 Chicago Hidden Gems to Explore This Fall

If you want your home to stand out this Halloween, Woolly Mammoth offers cool and creepy items that you won’t find anywhere else. Run by a husband and wife, this Andersonville shop offers everything from taxidermy, to old dental slides, to Ecuadorian shrunken heads. If you really want to get spooked, check out the cartoon of Hitler drawn by serial killer John Wayne Gacy (not for sale). Safe shopping is in place with required face coverings and a limit of five people in the store at a time.

Support Sustainable Food Businesses at The Plant

10 Chicago Hidden Gems to Explore This Fall

A former meatpacking plant in the Back of the Yards neighborhood is reimagined as a sustainable food community known as The Plant. The facility is home to 20+ food businesses committed to material reuse and closed-loop systems including a coffee roaster, bakery, and kombucha brewery. Shop very local by supporting their outdoor market (every Sunday through October), order goods online, or raise a glass at Whiner Beer’s taproom (operating at 25% capacity).

Recreate Michelle and Barack’s First Date! 

10 Chicago Hidden Gems to Explore This Fall

Who better to look to for date night inspo than Chicago’s first couple? Barack and Michelle Obama shared their first kiss in 1989 at a Hyde Park Baskin-Robbins, and there’s a plaque marking the sweet spot. Fortunately for us, there’s still a Baskin-Robbins in the 53rd St. strip mall. Order a chocolate cone, like Michelle did, and smooch your sweetie. Afterward, soak in an incredible skyline view from Promontory Point or peep at the changing leaves in Jackson Park

Take a Trapeze lesson in a 112 Year Old Logan Square Chuch 

10 Chicago Hidden Gems to Explore This Fall

You would never guess that this Logan Square church is hiding a circus school inside! Aloft Circus Arts offers classes in things like trapeze, aerial silks, and trampoline ranging from the circus curious to a program for professionals. In-person classes are subject to COVID safety policies. If you’re not ready to go pro, try something new with Aloft’s online classes. From handstands, to stretching, to juggling there are plenty of opportunities to pick up a new skill from home.

Hike to a Buried Nuclear Reactor in Forest Preserve

Hike to a Buried Nuclear Reactor in Forest Preserve

Hike to a bit of world history in the Cook County Forest Preserve—but watch your step! After the world’s first nuclear reactor took place in Chicago, the reactor moved to a facility near today’s Red Gate Woods. When the lab was decommissioned, the reactor was buried in the woods. There are two nuclear burial sites in the park, and I’ve got a video on how to find them here

Celebrate Hispanic Heritage Month at Dulcelandia

Celebrate Hispanic Heritage Month at Dulcelandia

Hispanic Heritage Month runs through October 15, and my favorite way to celebrate is by stocking up on Mexican candy. Dulcelandia is a family-run business that offers the largest selection of Mexican candy in the Midwest. Their 600+ varieties of sweets include flavors you won’t find elsewhere like tamarind, mango, and marzipan. Check out their Chicago locations in Little Village, Logan Square, and Brighton Park. 

Take a Self-Guided Tour of Pothole Art

Take a Self-Guided Tour of Pothole Art

Chicago has a pothole problem, but artist Jim Bachor’s solution is to fill them with art. Since 2013, he’s been installing works of mosaic art in potholes on the city streets. His mosaics find beauty in the ordinary like a bouquet of flowers or a bag of Cheetos. This spring, he installed a COVID-inspired series including a bottle of Purell and roll of toilet paper complete with real gold leaf. Check out his website for a map of installations and hunt them down while social distancing. 

Taste a Mead Flight at Wild Blossom Meadery

Taste a Mead Flight at Wild Blossom Meadery

Did you know that mead is the world’s oldest alcoholic beverage? Fortunately, Chicago’s Beverly neighborhood is home to the first meadery in Illinois. Enjoy a flight of this honey wine in 12+ flavors at Wild Blossom Meadery. Their patio along the Dan Ryan Woods is open for a scenic and socially distanced visit.

Go on a Cemetery Scavenger Hunt

10 Chicago Hidden Gems to Explore This Fall

Hear me out— cemeteries are historic, nature-filled, and not too crowded. They’re a great place for a walk in this era of social distancing! Chicago’s cemeteries are filled with stories, but if I had to recommend one, I’d start by visiting the gorgeous Graceland Cemetery in Lakeview. If you really want to indulge in the spooky season, check out this scavenger hunt of historic graves I created for Chicago Magazine


Thank you SO much to Jessica for rounding up this amazing list of Chicago hidden gems for us! Whether or not you’re in Chicago, I hope this inspired you to seek out the unexpected wherever you live! For more secret spots check out her book, blog, or Instagram

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