It's my kind of spooky town, Chicago! That's what my latest visit to this icon of the Midwest had me singing, and I will be back soon for more spooky fun.
Admittedly, Chicago doesn’t always feel like a getaway to me. I grew up visiting my dad’s side of the family there every other summer, so we’ve done it all: the museums, the zoos, the Sears Tower (none of that Willis nonsense here, thank you).
But one thing I hadn’t done in my adult visits? Check out the spooky side of the city.
I had a great starting place, thanks to Splash of Spooky’s article in the fall 2024 full-size issue of Spooky Little Halloween—The Magazine. On my trip over for Midwest Haunter’s Convention this year, the Internet helped me find even more year-round spots to visit.
Here are six I stopped by, as a tourist, and whether or not I would recommend them for fellow visitors — plus five more recommendations for my next trip!
Spooky things to do in Chicago
October Cafe
6046 N. Avondale Ave.
Chicago, IL 60631
octobercafe.com
We’ll start with a (spoiler alert!) personal favorite spot in the Windy City: a fall-themed coffee shop where pumpkin spice is on the menu all year long! October Cafe is the most delightful spot you could imagine — like you just walked into the coffee shop in Halloweentown.
They serve Dark Matter Coffee, locally roasted, and serve a variety of food and pastries (all vegan!). There is plenty of seating throughout the shop, and you’ll enjoy how their team call everyone “pumpkin.”
Be sure to ask about their monthly flights too!
Would I recommend it?
DUH. If I could live at October Cafe, I would. It’s the cutest spot, and those pumpkin lattes hit just right when I show up in June every year. Plus owners Audrey and Michelle are just about the sweetest human beings in the world.
See more of this spot in the summer 2024 fun-size issue or the fall 2024 full-size issue of the magazine.
The BRewed Coffee
2843 N. Milwaukee Ave.
Chicago, IL 60618
thebrewedcoffee.com
I love the rise of the horror coffee shop, and The Brewed is one of Chicago’s other spooky coffee offerings.
This horror-themed shop, located in the Avondale neighborhood, has a seasonal themed menu along with coffee shop classics. The space is full of Halloween and horror collectibles, making it a delight to wander before finding a spot to post up.
Seating options are plentiful and varied, from a cozy couch to barstools to booths. They also host regular events, such as the bi-monthly Chicago Monster Mart, and even have their own members-only movie club.
Would I recommend it?
YES! I loved spending some time here with a friend when I visited, and my drink (the Firestarter, a tangerine ancho chili latte inspired by the Stephen King novel) was delicious. I can’t wait for the next visit to the city so I can return and try another seasonal drink.
Bonus points for this being within reasonable walking distance (10-15 mins through a neighborhood) from a Blue Line station too.
The Horror House
If you’re stopping by The Brewed, you’d be remiss not to take a walk across the street to The Horror House. Since 2022, this spot has offered up Halloween and horror collectibles, tricks, and treats.
Inside you’ll find everything from T-shirts and posters to unique jewelry, collectible toys and movie memorabilia. They also have a nice selection of magazines and zines.
Would I recommend it?
If you’re nearby, definitely! It’s a smaller space and a quick wander, but if you’re on the hunt for a specific or already planning to visit The Brewed (their front doors basically face each other) it’s worth the stop.
Sideshow Gallery
2219 N. Western Ave.
Chicago, IL 60647
sideshowgallerychicago.com
Whether it’s candles and tarot cards or unique jewelry and bath products you’re looking for, Sideshow Gallery has a little something for everyone who is witchy at heart.
This shop is small, but mighty. It’s beautifully decorated, cozy, and feels like such a hidden gem tucked away on a busy street just off the Kennedy Expressway.
In addition to shopping, Sideshow Gallery hosts regular classes and events if you’re looking to learn more about tarot, participate in a full moon ritual, or even join their book club!
Would I recommend it?
Definitely! Minneapolis is a little lacking in classic new age/occult shops, so stopping by Sideshow was such a delight. Inside was stunning, and I probably could have wandered in circles for hours and spotted something new every time. It’s absolutely a spot I’ll return to when I’m in town next.
Bucket O’Blood Books & records
3182 N. Elston Ave.
Chicago, IL 60618
bucketoblood.com
Looking for hard-to-find horror books, music, or movies? Then you need to stop by Bucket O’Blood!
In addition to large inventory of rare and collectible books, the shop has a huge vinyl section, wide variety of recent horror book releases, and even a killer graphic novel section. There’s also a full selection of new and used horror movies — you’re sure to find some hidden media gems here!
Bonus points: there are new and used options of everything.
Would I recommend it?
ABSOLUTELY! This ended up being my favorite — and most expensive — stop of the day. I’ve really fallen in love with specialty book stores in the last year, and Bucket O’Blood delivers for horror fans.
My favorite part: they had their Halloween records pulled into a special section so they were so much easier to find than most record stores. I stopped myself at three books and records, each, so I still had money for Midwest Haunters shopping the next day…
My only word of caution: this is off a busy intersection, and parking was sparse. Consider looking it up on Google Maps first for a parking plan if you’re like me (a typical millennial) and need to know the parking plan before you go.
Creepy Cruise | First Lady
112 E. Wacker Dr.
Chicago, IL 60601
firstlady.com/cruises/sightseeing-creepy
At nearly 200 years old, there is a lot of history in Chicago — including plenty of haunted history. During this 90-minute nighttime cruise on the Chicago River, you’ll learn more about the city’s shadowy past on and off the river from your tour guide.
This tour is only offered March through November. Indoor and outdoor seating is available, along with a full-service drink and snack bar on board. The Creepy Cruise sets sail rain or shine.
Would I recommend it?
Yes, but that is a tentative yes. I’m glad I went. The views of the city at night were incredible. The stories we heard? Meh. That may have been personal perception of what I was getting into than anything. My expectation was stories specific to the areas we were cruising, and while there were stories that took place in iconic buildings downtown and on/in the river, there were plenty that simply tied into local lore.
At the end of the day, it was a fun adventure, but if you’re budgeting time or money this might be one to skip.
More spooky things to do in Chicago:
There were a handful of stops on my list that I didn't have time to do this trip, so here are a few more places to add to your spooky travel itinerary! (Listed alphabetically.)
Graveface Museum
1829 N. Milwaukee Ave.
Chicago, IL 60647
gravefacemuseum.com
Graveface, founded in Savannah, GA, opened a Chicago museum in 2022. Inside, you’ll find artifacts and decades worth of research on topics ranging from true crime, cults, sideshow history, aliens, the occult and more.
Their shop is what I wanted to check out most — I scored some cool spooky records from their online store after seeing them at Oddities & Curiosities Expo in St. Louis earlier this year.
Malliway Bros Magic & Witchcraft
1407 W. Morse Ave.
Chicago, IL 60626
malliwaybros.com
This was the spot I was most bummed I didn’t make it to this trip. In additional to selling the typical new age/occult wares you’d expect to find in a magic and witchcraft shop, Malliway Bros also hosts regular fortune tellers, prepares monthly shop spells for you to cast, has a make-and-take station, and sells a huge assortment of herbs for your own spell vials.
Occult Bookstore
3031 N. Milwaukee Ave.
Chicago, IL 60618
occultbookstore.com
Looking to learn more about the occult, pagan practices, or different types of magick? Drop by Occult Bookstore, located just half a mile north of The Brewed and The Horror House on North Milwaukee Ave., where every member of their staff is a skilled and experienced practitioner on the path of spirituality.
In addition to magickal supplies and books, Occult Bookstore also hosts regular classes and events. Be sure to check their hours before you go — they are only open in the afternoon!
Roots & Ritual
3435 N. Kedvale Ave.
Chicago, IL 60641
rootsandritual.com
One final witchy shop for the list! Roots & Rituals seeks to offer customers ancient remedies and sacred self-care rituals. Here you’ll find custom-made honeys and teas, salves and tonics, and a full schedule of events.
Windy City Ghosts
Meeting spots for tours are provided in booking details
windycityghosts.com
This was the ghost tour I should have opted for! Whether you want to learn more about Chicago gangs and mobsters, supernatural and ghost stories, or the Great Chicago Fire (which happened in October 1871!), US Ghost Adventures has the perfect tour option for you.
Which spooky spot in Chicago will you visit?
Share your picks from my list in the comments. Or, better yet, drop a pick for something not on my list in the comments!
