MomSkoop
Fall in Chicago means one thing: it’s time to embrace spooky nights out! Whether you’re coordinating a girls-night costume party, a date with flair, or a fun adult outing, we’ve found eight standout restaurants and bars where Halloween isn’t just an after-thought—it’s the main event.
From immersive décor and themed cocktails to full pop-ups built for photo ops and festivities, these spots bring the holiday energy in style. Grab your witches’ hats (or pumpkin earrings), make reservations now, and get ready to explore Chicago’s October scene.
1. Nightmare on Clark Street
The first stop is the wildly immersive experience at Nightmare on Clark Street, tucked inside Stolen Saddle. Opening for the 2025 season on October 10 and running through November 3, this haunting spectacle offers intense décor, multiple floors of thrills, and bar service with themed cocktails.
For the mom-crew or friends that love a little adrenaline, this one hits big: think house-of-horror meets Instagram-ready interior, with creative lighting and spooky zones that keep the ambiance high.
Pro tip: dress up, because the photo ops are everywhere and you’ll want to capture the full vibe—plus it’s a great excuse for matching Halloween outfits or a mini-costume moment before the weekend gets wild.
2. Boo-kini Bottom Halloween Pop-Up
Next up: dive under the sea at Boo‑kini Bottom, the Halloween pop-up at Replay Lincoln Park. For about $30 you get express entry and two cocktails, plus a totally themed atmosphere with décor and events that lean playful and nostalgic.
This isn’t your standard haunted lounge—think under-the-sea meets costume party meets cocktail bar. It’s perfect for a fun-loving group of moms who want to let loose a little, laugh, and enjoy something unexpected rather than full fright.
Plan ahead for a weekend night, and maybe coordinate a mini-theme with your friends (sea creatures, reefs, pineapple hats) to maximize the fun. Also check their calendar for costume contests or other events.
3. JoJo’s Pumpkin Patch
For something a little more relaxed (or family-friendly early in the evening), head to JoJo’s Pumpkin Patch at JoJo’s Shake BAR. Opening September 28, 2025, it features a patio filled with pumpkins, fall décor, seasonal shakes, festive cocktails, and space to hang out in style.
Whether you’re doing a mom-date with friends, or bringing a motivated tween for the photo backdrop, this spot nails cozy meets Instagram-worthy. You get the autumn aesthetic without diving into full-on horror (unless you want).
Tip: Grab a reserved table under one of their domes, order the big “shake” (yes it’s dessert-first!) and plan for early evening to snag the best views and photos before the nighttime crowd kicks in.
4. Never Trust the Living at The Dandy Crown
If cocktails and serious ambiance are your vibe, check out Never Trust The Living at The Dandy Crown. This dedicated Halloween pop-up bar runs from Sept 21 to Nov 3, 2025 and features art-filled spaces, devilishly themed drinks and a patio covered in decorations.
It’s a great fit for a “grown-up Halloween” night out: less jump scares, more stylish chill with immersive décor and clever mixology. The kind of place you can transition after dinner or make the evening itself.
Go earlier if you want to mingle and relax; later means it turns up a notch. Suggest arriving when the sun sets to see how the lighting enhances the mood and décor.
5. Jack’s Pumpkin Pop-Up
For something bigger-scale and outdoor-friendly, the Jack’s Pumpkin Pop‑Up on Goose Island delivers. Spread over two acres, it features the city’s largest corn maze, 10,000+ pumpkins, carnival games, hidden bars, axe-throwing stations and more. Running through November 2, 2025.
This one plays both kids-friendly (early) and adult-fun (later): you could start here for a family outing then head for cocktails once the sun sets. For moms who want “Instagram + activity + drinks,” this is gold.
Advice: buy tickets in advance, plan parking (Goose Island gets busy), and if you can, schedule during off-peak to enjoy the maze without feeling rushed. Bonus: coordinate spooky-fall picnic vibes or grab a flannel and comfy shoes.
6. Sweet Dreams: The Halloween Experience at Rizzo’s Bar & Inn
Stick out a night of immersive horror-themed fun at Sweet Dreams: The Halloween Experience inside Rizzo’s Bar & Inn in Wrigleyville. The space transforms into a 20,000-square-foot indoor/outdoor haunt where scenes from 20 classic horror movies collide.
This one is for when you and your crew want full commitment to the Halloween theme—dress up, go bold, and expect nightmarish fun. It’s less casual than a regular night out, but hugely memorable.
Tip: wear comfortable but cool wardrobe (you’ll walk and explore), drink responsibly, and maybe split rideshares if you’re going after 10 pm. It’s perfect for making a Halloween night of it with friends.
7. Halloween Town at Tree House Chicago
When you’re craving celebration plus spectacle, hit Halloween Town at Tree House Chicago in River North. This pop-up transforms the venue into a full “The Nightmare Before Christmas”-inspired world, with glowing pumpkins, themed cocktails, photo installations and family-friendly until a designated hour.
It hits that sweet spot: you can bring younger kids early on (depending on time) or make it a fun adult outing after dinner. Tons of visuals for your feed, and the vibe is inclusive and festive.
For best experience: visit in the early evening to enjoy decor + food then stay for cocktails if you’re staying out. Reservation recommended since themed pop-ups fill fast.
8. The Haunted Tavern
Last but definitely not least, check out The Haunted Tavern—a themed, ticket-only cocktail journey (about 90 minutes) at a haunted venue in Chicago, where you move through four interactive “chapters” while sipping curated drinks and hearing chilling back-stories.
This is ideal for a paired-down, grown-up Halloween outing: fewer people, more immersive story and drink-focus. If you’re looking to celebrate with your partner or a small group of friends, this is perfect.
Pro tip: treat this like a show—arrive early, dress smart-casual, and leave room for a follow-up drink somewhere nearby so you don’t feel rushed out after the 90-minute session.