The Ultimate Chicago Halloween Bucket List

It’s officially spooky season and there are many thrilling, Halloween-related activities to do this year in Chicago. Every year, the city comes alive during October with fall festivities like picking pumpkins, watching Halloween-themed parades, and watching scary movies. If you’re looking for something to do this Halloween in Chicago that is exciting—and maybe just a little bit frightening—look no further. Here’s the ultimate 2021 Chicago Halloween bucket list.

Go see Navy Pier’s Pier Pumpkin Lights

This year, you can do a variety of Halloween-inspired activities at Navy Pier. One popular activity is the Pier Pumpkin Lights, which transforms the Pier into an insta-worthy fall spectacle with nearly 1,000 pumpkins throughout October. Additionally, you can go on Saturdays to experience Slightly Spooky Saturdays, which are free themed events that include magicians, movies, costume parties, and trick-or-treating from October 9 to 30. 

Take a Gangsters and Ghosts Tour of Chicago

Go on a 2-hour guided walking tour through the Chicago Loop and discover the spooky stories of gangsters and ghosts from the city’s past. You’ll be able to see the places where gangsters, such as Al Capone, used to party, make deals, and carry out threats. Additionally, you’ll be able to visit haunted locations and old crime scenes. Some of the places you’ll stop at include the Congress Hotel and Death Alley.

Commemorate Day of the Dead

Although Day of the Dead is after Halloween on November 2, it is still a fun holiday to celebrate. To celebrate this traditional Mexican holiday, visit the National Museum of Mexican Art to see their annual exhibit for the Day of the Dead. The exhibit, Día de Muertos – A Time to Grieve & Remember, runs from September 10 to December 12.

Watch a scary movie at a drive-in

If you’re a fan of scary movies, then this activity is perfect for you. This month, Music Box Theatre is showing spooky movies at the Chi-Town Movies Drive-in. Showings include the Bride of Chucky, The Exorcist, American Psycho, and more. If you don’t have a car, there are also spots for chairs.

Attend a Halloween parade

This year, there are a few Halloween parades that you can choose to attend. One is Arts in the Dark, an evening parade that celebrates art and artists. There will be unique floats, spectacle puppets, and creative performances against the backdrop of historic State Street on October 30. Another popular parade, the Haunted Halsted Halloween Parade—and costume contest—takes place on October 31 on North Halsted Street. It will feature fire-breathing performers and an all-girl cover band.

Stoll through the Night of 1,000 Jack-o’-Lanterns

While visiting Lincoln Park Zoo this month, you can stroll through the Night of 1,000 Jack-o’-Lanterns, a pathway that displays more than 1,000 hand-carved pumpkins. Along the way, you’ll be able to see pumpkins carved by professionals that include images of superheroes and celebrities. In addition to the pumpkins, there are also costumed entertainers, live carving demos, and food and drinks for sale.

Planning your visit

Whether you choose to visit Chicago this fall or in the future, you’ll have a unique and exciting experience. After you’ve selected your travel dates, you’ll need to decide where you’ll stay on your trip. Consider booking a hotel located in the heart of the city, close to many of these spooky activities. Now you’re ready for your upcoming trip to Chicago filled with breathtaking adventures and spectacular sights. 

Need a place to stay when visiting Chicago? Book your reservation here.