8 Spooky Halloween Date Ideas around Chicago and the Suburbs

It’s cold, it’s spooky – it’s cuffing season! Whether you’re in a long-term relationship (don’t rub it in) or still searching for the love of your life, Fall is the best time to ignite that romantic spark. This time of the year, dates often get less exciting as you’re forced indoors due to impending inclement weather and are generally just looking to stay cuddled up on the couch. This Halloween season, our goal is to get you out of the house with some not-so-basic date ideas that’ll have you and your partner laughing together, jumping into each other’s arms, and warming up this chilly season with some romance.

Looking for the full-on spooky experience from top to toe to fur babies? Don’t forget to check out our ultimate Chicago Halloween activity guide!


Sweet Dreams – The Halloween Experience

3650 N Clark St, Chicago, IL 60613


Tis’ the season to be SCARED, and that’s exactly what you’ll be getting yourself into at Sweet Dreams – The Halloween Experience. This scary movie-themed pop-up event is quite literally perfect for the spooky season. Sweet Dreams is where 25 classic horror movies collide and you get to experience it all at the same time. Add some cocktails and you’re all set for the perfect date night! Tickets for this event start at $10 and include entry into the event and one complimentary drink, so pick out your best Fall fits and get ready to be bombarded with scary movies, in the best way. 

Sonny Acres Farm

29W310 North Ave, West Chicago, IL 60185

While there are pumpkins, treats, and activities for the whole family, Sonny Acres Fall fest takes Halloween-themed date ideas to the next level. If you’re looking for your partner to get scared right into your lap, take them on the haunted hayride where you’ll travel the grounds on a tractor and hold in your highest screams as creatures and characters jump out of the woods. After your heart rates return to normal, take your seasonal picture on the “Sit N Kiss” log, and start racking up those likes, baby! 


The Drake

140 E Walton Pl, Chicago, IL 60611

If you didn’t know, The Drake is notoriously haunted AF. Since opening in 1920, the Drake has been visited by celebrities, gangsters, and the famous Lady in Red. It’s said that the Lady in Red found her husband cheating on her in a room on the tenth floor, where she jumped to death. If you and your partner want to dabble on the paranormal side this Halloween season, we dare you to request a room on the tenth floor and do a little ghost hunting for yourselves. This year, they’re also doing an awesome Spooky afternoon tea program that is sure to take the thrilling romance to a whole new level.

spooky date idea in chicago gangster tour
Image Credit: Viator.com

Chicago Gangster and Ghost Tour

71 E Wacker Dr, Chicago, IL 60601

Chicago history is quite the story, and with this 2-in-1 walking tour, you and your sweetheart can enjoy the notoriety of Chicago’s classic gangsters and the famous ghosts who still haunt the city’s oldest buildings. Favorite stops include the Palmer House, Congress Hotel, and Chicago Theater, where you’ll hear all the details and secret’s about Chicago’s rich past. Previous tour goers recommend comfortable shoes, as this does require a lot of walking, but you’ll rest assured knowing you’re expanding your history on the city, spending a fun night with your partner, and perhaps encountering a ghost or two in the process. 

Halloween Wine Tasting – The Wine Cellar Outlet

3021 Butterfield Rd, Oak Brook, IL 60523

BOO(ze)! This October, head to the Wine Cellar Outlet in Oak Brook (right off 88) for their famous Halloween Wine Tasting. On October 20th from 6:00-7:30 PM, you’ll be able to test out some of the store’s favorite bottles that will pair perfectly with your Halloween festivities, even if that just includes downing like, three king-size Snickers bars on the 31st. The best thing about the Wine Cellar? You’ll likely learn about vineyards and labels you’ve never heard of because all their wine is boutique and hand selected for their stores. Want to do your wine shopping online with your lover? Head to https://shop.thewinecellargroup.com/ to have wine shipped right to your door. 

Fantasy Costumes

4065 N Milwaukee Ave, Chicago, IL 60641

Playing dress-up with your friends is something you used to love doing as a kid, so why not bring that into your relationship too? Fantasy Costumes is one of the oldest costume shops in the city, which makes it a perfect spot to spend the afternoon with your lover, picking out the perfect costumes for Halloween and, cough, beyond. From disco dancers to animals to superheroes, take some time to pick out a plethora of perfect costumes and laugh together as you realize how silly you look dressed up. Bonus, Fantasy Costumes has great outfits if you and your partner like dressing up all year long (wink). 

ChiTown Movies

2343 S Throop St, Chicago, IL 60608

I truly don’t think there’s anything more romantic than a drive-in movie with your honey. Tons of comfy pillows and blankets surrounding you? Check. Your favorite snacks? Yup! Getting scared and finding solace in each other’s arms? You know it. This spooky season, head to ChiTown Movies where you and your partner can snuggle up and watch some of the most popular Halloween movies. From scary to silly, enjoy a movie night somewhere other than your couch. Don’t forget, rates per car starting at $33! 

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