Spooky Things to Do in Chicago This Halloween

Already finished every movie in the “A Nightmare on Elm Street” franchise before fall even officially started? It’s time to take the horror outdoors. Chicago comes alive in October with seasonal celebrations so here is your ultimate guide to the best spooky things to do in Chicago this Halloween.

Jack’s Pumpkin Pop-Up

Looking for a great place to experience fall without leaving city limits? There’s no better place for fall festival vibes than Jack’s Pumpkin Pop-Up. Open every day until November 1st, you can expect family-friendly activities like corn mazes, carnival games, gem mining, and of course, exploring the pumpkin patch. You can also enjoy alcoholic drinks at the full bar on site, and try your hand at more adult activities like axe throwing and Instagram-worthy photo ops among the 10,000+ pumpkins and fall decor. 

Catch “The Rocky Horror Picture Show” with Original Cast Members

There’s truly no better way to experience “The Rocky Horror Picture Show” than in a packed theater on Halloween night. Unless, of course, you manage to host it with three of the film’s original stars—which is exactly what’s happening on October 31st at the Chicago Theatre.  Catch the 4K restoration of the film on its Spooktacular Tour and be sure to schedule a meet and greet for extra immersion. 

Take a Creepy Cruise with First Lady 

Trying to find something unique for your Chicago Halloween agenda? If you’ve already experienced our award-winning architecture tour and you’re looking for a spine-tingling waterborne adventure, look no further than our Creepy Cruise. These 90-minute nighttime cruises focus on the shadowy figures and haunting tales from the Windy City’s wild history. Our tour guides flex their storytelling muscles with some truly terrifying stories. Our boats are outfitted with a full bar with seasonal specialties, spacious decks for covered or open-air viewing, and restrooms so you’re never without comfort. 

Hop on the Howl-O-Ween Canine Cruise

If you want to try something spooky with your four-legged friend, why not hop aboard our Howl-O-Ween Canine Cruise? The event, hosted on the third and fourth weekends in October, gives you 90 minutes aboard one of First Lady’s spacious vessels. Get in the autumnal spirit with a costume contest for you and your pet! Your dog can enjoy pumpkin-flavored treats and have plenty of tail-wagging fun socializing with other pups.

Celebrate Spooky Season with First Lady

From haunting Chicago history to fun pet costumes, First Lady is thrilled to bring the magic of Halloween to the water this autumn. Spaces on our seasonal cruises are strictly limited and sell out quickly every October. Finalize your costume, grab your favorite ghoul (or dog!), and book your tour to celebrate the spooky season from the best view in the city.