8 Scary Chicago Date Ideas to Handcuff “The One”


It’s cold, it’s scary – it’s handcuff season! Whether you’re in a long-term relationship (don’t stress) or you’re still looking for the love of your life, fall is the best time to ignite that romantic spark. At this time of year, dates often become less exciting as you’re forced to come indoors due to impending bad weather and you’re usually looking to cuddle up on the couch. This Halloween season, our goal is to get you out of the house with some not-so-basic dates that will have you and your partner laughing together, jumping into each other’s arms, and warming this cold season with a bit of romance.

Looking for the complete scary experience from head to toe to furry babies? Be sure to check out our ultimate Chicago Halloween activity guide!

3650 N Clark St, Chicago, IL 60613

It’s the season for being scared, and that’s exactly what you’ll be getting yourself into at Sweet Dreams – The Halloween Experience. This spooky movie-themed pop-up event is literally perfect for spooky season. Sweet Dreams is where 25 classic horror movies come together and let you experience it all at once. Add some cocktails and you are ready for the perfect evening! Tickets for this event start at $10 and include event admission and a free drink, so pick your best fall cuts and prepare to be bombarded with scary movies, in the best way.

29W310 North Avenue, West Chicago, IL 60185

While there are certainly pumpkins, treats, and activities for the whole family, the Sonny Acres Fall Festival takes your Halloween-themed get-together to the next level. If you’re looking to get your partner scared on your knees, take them on the Haunted Wagon Ride where you’ll roam the grounds on a tractor and hold back your high-pitched screams as creatures and figures leap out of the woods. Once your heart rate is back to normal, take your seasonal photo on the “Sit N Kiss” journal and start racking up those likes, baby!

140 E Walton Pl, Chicago, IL 60611

If you didn’t know, The Drake is notoriously haunted AF. Since its opening in 1920, the Drake has been visited by celebrities, gangsters and the famous Lady in Red. The Lady in Red is said to have found her husband cheating on her in a bedroom on the tenth floor, where she jumped to her death. If you and your partner want to try your hand at the paranormal this Halloween season, we challenge you to request a room on the tenth floor and do a little ghost hunting on your own. This year they are also hosting a spooky afternoon tea program that is sure to take the thrilling romance to a whole new level.

Image Credit: Viator.com

71 E Wacker Dr, Chicago, IL 60601

Chicago’s history is quite the story, and with this 2-in-1 walking tour, you and your sweetheart can enjoy the notoriety of classic Chicago gangsters as well as the famous ghosts that still haunt the city’s oldest buildings. Famous stops include the Palmer House, Congress Hotel, and Chicago Theater, where you’ll hear all the details and secrets of Chicago’s rich past. Previous visitors recommend comfortable shoes, as it requires a lot of walking, but you’ll be sure to know you’re expanding your story about the city, having a fun night with your partner, and maybe encountering a ghost or two in the process.

3021 Butterfield Road, Oak Brook, IL 60523

Booze)! In October, head to the Wine Cellar Outlet in Oak Brook (just off 88) for their famous Halloween wine tasting. On October 20 from 6:00 p.m. to 7:30 p.m., you can sample some of the store favorites that will pair perfectly with your Halloween festivities, even if that only includes drops like three king-size Snickers bars on 31. The best thing to about the wine cellar? You’ll likely learn more about vineyards and labels you’ve never heard of, because all of their wine is boutique and hand-selected for their stores. Want to shop for wine online with your lover? Head toward https://shop.thewinecellargroup.com/ to have the wine shipped right to your door.

4065 N Milwaukee Ave, Chicago, IL 60641

Playing dress up with your friends is something you loved to do as a kid, so why not incorporate that into your relationship too? Fantasy Costumes is one of the oldest costume shops in town, making it a great place to spend the afternoon with your sweetheart, picking out the perfect costumes for Halloween and, cough, beyond. From disco dancers to animals to superheroes, take the time to pick out a plethora of perfect costumes and laugh together realizing how silly you look dressed. As a bonus, Fantasy Costumes has some great outfits if you and your partner enjoy dressing up all year round (wink).

2343 S Throop St, Chicago, IL 60608

I really don’t think there’s anything more romantic than a walk to the movies with your sweetheart. Tons of comfy pillows and blankets surround you? Check. Your favorite snacks? Yeah! Being afraid and finding comfort in each other’s arms? You know. This spooky season, head to ChiTown Movies where you and your partner can cuddle up and watch some of the most popular Halloween movies. From scary to wacky, enjoy movie night away from your couch. Remember, per-car rates start at $33!

Featured Image: Unsplash


Comments are closed.