Chicago transforms into a thrilling playground during Halloween, offering endless options for those looking to celebrate the spooky season. From haunted houses and ghost tours to festive bar crawls and family-friendly events, the Windy City is brimming with activities to suit all ages and tastes.

Whether you want to immerse yourself in Chicago’s creepy history, dress up for a night out on the town, or indulge in some fall-themed treats, there’s no shortage of ways to get into the Halloween spirit.

Fun Things to Do on Halloween in Chicago​

If you’re a resident of Chicago or just visiting for a short break over Halloween you might want to check out our list of great fun ideas we’ve compiled. Read on to discover some of the best things to do in Chicago for Halloween!

• Night of 1000 Jack-o-Lanterns
• Halloween in the Parks
• Chicago Halloween Parade
• Halloween Bar Crawl
• Halloween House Music Party
• Haunted Halloween Monsters’ Ball
• Halloween Day Crawl in River North
• Chicago Halloween Party Cruise – Titanic Masquerade

Night of 1000 Jack-o-Lantern

The Night of 1000 Jack-o-Lanterns is a must-see Halloween event in Chicago that’s sure to delight visitors of all ages. This enchanting display features thousands of hand-carved pumpkins illuminated by LED lights, creating a magical and spooky atmosphere that’s perfect for the Halloween season.

As you stroll through the illuminated trails, you’ll be amazed by the creativity and artistry on display. Each pumpkin is a unique carving, showcasing the talents of local carvers.

In addition to the stunning pumpkin display, the Night of 1000 Jack-o-Lanterns also offers a variety of other activities for the whole family. Children can enjoy face painting, games, and crafts, while adults can sip on hot cocoa and explore the beautiful grounds of the Chicago Botanic Garden. There’s something for everyone to enjoy at this festive event.

If you’re looking for a fun and memorable way to celebrate Halloween in Chicago, the Night of 1000 Jack-o-Lanterns is a must-see. This event is a great opportunity to create lasting memories with your family and friends.

Halloween in the Parks

Halloween in the Parks is a popular annual event in Chicago that offers a variety of spooky fun for the whole family. Each year, parks throughout the city host Halloween-themed activities, games, and crafts. From trick-or-treating and costume contests to haunted houses and hayrides, there’s something for everyone to enjoy.

One of the highlights of Halloween in the Parks is the costume contest. Children and adults of all ages can show off their creative costumes and compete for prizes. There are also plenty of games and activities for kids, including pumpkin carving, face painting, and spooky storytelling.

For those looking for a more thrilling experience, some parks offer haunted houses or haunted trails. These attractions are designed to scare, so they may not be suitable for young children. However, older kids and adults who enjoy a good scare will love these spooky adventures.

Halloween in the Parks is a great way to celebrate Halloween with your family and friends. It’s a fun and affordable event that’s perfect for kids of all ages. So grab your costume and head to your local park for a night of spooky fun.

Chicago Halloween Parade

The Chicago Halloween Parade is a lively and exciting annual event that showcases the creativity and spirit of the city’s residents. This colorful parade features floats, marching bands, costumed performers, and more. It’s a must-see event for anyone looking for a fun and festive way to celebrate Halloween.

The parade typically begins in the heart of downtown Chicago and winds its way through the city streets. As you watch the parade, you’ll be amazed by the variety of costumes on display. From classic characters to original creations, there’s something for everyone to enjoy.

In addition to the parade, there are also often pre- and post-parade activities. These may include live music, food vendors, and other family-friendly entertainment. It’s a great opportunity to spend the day with friends and family and soak up the festive atmosphere.

The Chicago Halloween Parade is a truly unforgettable experience. Whether you’re a local or a visitor, it’s a must-see event that will leave you with lasting memories.

Halloween Bar Crawls

Halloween bar crawls are a popular way to celebrate Halloween in Chicago. These events typically involve a group of people visiting multiple bars and clubs on a designated night. Participants often dress in costumes and enjoy Halloween-themed drinks and specials.

Try the Chicago Halloween Bar Crawl. This crawl also takes place in River North on October 26th and features a variety of spooky bars. So take your ghoulish friends and enjoy some ghostly DJ sets, costume contents and themed cocktails, the night is bound to be alive.

Halloween House Music Party

The Halloween House Music Party is a popular annual event that brings together music lovers and Halloween enthusiasts. This event typically takes place at a nightclub or other large venue and features a lineup of house music DJs. The atmosphere is electric, with people dancing and celebrating in their Halloween costumes.

The Halloween House Music Party is a great way to have fun and meet new people. It’s also a great opportunity to show off your Halloween costume and win $1000 in a costume contest! If you’re a fan of house music and Halloween, this event is definitely for you.

Haunted Halloween Monsters Ball

The Haunted Halloween Monsters Ball is one of Chicago’s most popular Halloween parties. It takes place at the much-loved Hard Rock Cafe and features live music, dancing, and a costume contest.

The Haunted Halloween Monsters Ball offers a night of spooky fun with live music, dancing, and a costume contest. A DJ will spin dance music all night long, while guests can show off their creative costumes and compete for a cash prize. The Hard Rock Cafe will be transformed into a haunted wonderland with spooky decorations, and thrill-seekers can explore a haunted house on-site.

The event is open to guests 21 and over, and tickets are available online or at the door. The Haunted Halloween Monsters Ball is a great way to celebrate Halloween with your friends and have a night to remember.

Halloween Day Crawl in River North

Looking for an exciting way to celebrate Halloween in Chicago? Head to the Halloween Day Crawl in River North, one of the city’s most anticipated annual events. This lively bar crawl combines great food, drinks, live music, and a vibrant party atmosphere, making it the perfect way to enjoy Halloween in one of Chicago’s most popular neighborhoods.

The Halloween Day Crawl kicks off at noon and continues into the late evening, offering participants a full day of festive fun in the heart of River North. With a pre-purchased wristband, you’ll gain access to multiple participating bars and restaurants featuring discounted drinks, food specials, live music, and themed entertainment. Many venues will host costume contests with prizes for the best-dressed, and the entire neighborhood will be decked out in spooky decorations, creating a lively, Halloween-themed atmosphere perfect for mingling and celebrating the holiday.

Chicago Halloween Party Cruise – Titanic Masquerade

The Chicago Halloween Party Cruise is a unique and festive way to celebrate Halloween. This event takes place on a boat that cruises along the Chicago River and Lake Michigan and this year’s theme is Titanic Masquerade! The cruise features a variety of Halloween-themed activities, including a costume contest, live music, dancing, and a DJ.

The cruise also offers a variety of food and drinks, including a Halloween-themed buffet and specialty cocktails. The atmosphere is festive and fun, and it’s a great way to spend an evening with friends and family.

No matter how you choose to celebrate, Halloween in Chicago is an experience like no other. With so many unique events and activities, you’re sure to find something that sends a shiver down your spine or brings a smile to your face. From haunted attractions and costumed pub crawls to pumpkin patches and family-friendly festivities, the city offers something for everyone to enjoy.

If you’re planning a Halloween getaway to Chicago, be sure to secure your accommodation early! For convenience and comfort, book your stay through ParkSleepFly.com to find great airport hotel and parking deals near Chicago O’Hare Airport (ORD) and Chicago Midway Airport (MDW), that will make your trip even more hassle-free.

Enjoy the festivities without worrying about where to stay or park—start planning your perfect Halloween escape now!

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