As the air turns crisp and the leaves start to fall, Lakeview East transforms into a Halloween lover’s dream! From haunted happenings to spooky-themed events, there’s no shortage of festive fun in the neighborhood. Whether you’re looking for family-friendly activities or something a bit more eerie, we’ve got you covered.

Be sure to check back often, as we will continue to update this page as we find more events happening around the neighborhood!

Little Monster’s Crawl | October 26th 11AM to 3PM | Neighborhood Wide

Mark your calendars for the Little Monsters Crawl, happening on October 26th! Bring your little ghouls and goblins for a day of trick-or-treating fun around Lakeview East. With family-friendly activities, treats for the little monsters and goodies for their Big Monsters, it’s the perfect way to celebrate Halloween in the neighborhood. Don’t miss out on this spooky adventure! Partipating Locations have been announced! Click here!

Located in the Bamboo Club, this Halloween-themed bar is back! Both a bar and a haunted house, Nightmare on Clark Street is perfect for a Halloween-filled night. Experience their terrifying haunted house, then get a Halloween-themed cocktail to end the night. This is an experience you do not want to miss!

Go to their website to find their seasonal hours and cocktail menu!

Wrigleyville Halloween Crawl

Saturday, October 26th

Get ready for Chicago’s biggest Halloween party—the Wrigleyville Halloween Crawl! On Saturday, October 26th, join hundreds of costumed party-goers for an unforgettable night of bar-hopping through Wrigleyville’s hottest spots. With admission, you’ll get access to multiple bars, a costume contest, drink specials, and giveaways. Whether you’re dressing up as something spooky, silly, or downright creative, this crawl is the perfect way to celebrate Halloween in the heart of the city. Don’t miss out on the fun—grab your tickets and get ready for a hauntingly good time! Order tickets early for a cheaper price!

Haunted Halsted Halloween Parade

October 31st, 7:30 pm

Don’t miss one of the most exciting Halloween events in the city – the Haunted Halsted Halloween Parade! This iconic parade, taking place on October 31st, is a must-see spectacle in Northalsted. Featuring fabulous costumes, spooky floats, and live entertainment, it’s the perfect way to cap off the Halloween season. Whether you’re dressing up to join in the fun or just coming to watch the festivities, the energy and creativity on display are sure to amaze. Plus, there’s a costume contest with fantastic prizes, so bring your A-game and get ready for a night of Halloween magic!

Alamo Horror-House

Terrifying new titles & Halloween classics risen from the grave! Bio-exorcists! Alien symbiotes! Two different but equally terrifying clowns! Alamo Drafthouse in Wrigleyville has some pretty scary characters worthy of the pulpiest of headlines heading your way for Alamo Horror-House. Steel your nerves and head into the darkness with us to take on the most terrifying new titles and some chilling horror legends.

Smoke Daddy presents: movie night Wednesdays

You know what pairs perfectly with a horror movie? Scary good BBQ! Smoke Daddy in Wrigleyville is hosting Movie Night Wednesdays throughout October, starting at 6:30 pm.

Sketchual Education Presents: Enough With the Boo Sheet!

Tuesdays October 1st, 8th, 15th, 22nd, and 29th at 8:00 PM

Looking for a laugh this Halloween season? Don’t miss Sketchual Education’s Enough With the Boo Sheet! every Tuesday in October at 8:00 PM. This spooky variety show is packed with comedy, sketches, and more to get you in the Halloween spirit. It’s the perfect mix of scares and chuckles for those looking to enjoy the lighter side of the season. Head over to The Annoyance Theater and grab your tickets before they disappear!

Penne BOO-gate!

Wednesdays October 2nd, 9th, 16th, 23rd, and 30th at 8:00 PM

Back by popular demand, Penne BOO-gate! is here to fill your Wednesday nights with spooky entertainment! Filmed live at The Annoyance Theater, this Halloween special will have you laughing out loud as Penne Rigate navigates a world of hilarious horror. Monsters, curses, and unimaginable terror await—so join the fun and grab your tickets for a Wednesday filled with frights and laughs.

Summer Scaries: The Improvised Teen Horror Musical

Wednesdays October 2nd, 9th, 16th, 23rd, and 30th at 9:30 PM

Get ready to sing and scream with Summer Scaries: The Improvised Teen Horror Musical! Every Wednesday in October at 9:30 PM, this completely improvised musical will have you on the edge of your seat, blending nostalgic teen horror tropes with audience suggestions for a night of unpredictable fun. Whether it’s a haunted eyelash curler or a cursed film projector, each show brings a new twist to the world of teen horror. Don’t miss it!

Burlesque Is Gore

Fridays October 4th, 11th, 18th, and 25th at 8:30 PM | Halloween Special on October 31st at 10:30 PM

Prepare yourself for a night of spooky, sexy fun at Burlesque Is Gore! Held every Friday in October at 8:30 PM, and with a special Halloween edition on October 31st at 10:30 PM, this show is a must-see. It’s a thrilling blend of burlesque and Halloween mischief that will have you laughing, gasping, and maybe even a little spooked. If you’re a fan of the sultry side of Halloween, this event is for you! Grab your tickets and get ready for an unforgettable night at The Annoyance Theater.

Spooktacular Sing-Along

October 29th, 7 pm

Katy on Keys will be hosting a Spooktacular Sing Along on Tuesday, October 29th at NOLA Bar & Kitchen in Wrigleyville! Sing along to Halloween favorites, win prizes, and sip on themed cocktails and shots.

Cesar’s Killer Margaritas’ Spooky Margaritas and Día de los Muertos Ofrenda

Stop by Cesar’s Killer Margaritas throughout October to enjoy their special Spooky Margaritas, featuring flavors like La Catrina (Mango & Raspberry), El Corazón (Strawberry), and Black Widow (Blackberry). While you’re there, take part in their Día de los Muertos Ofrenda by bringing photos of loved ones to add to their altar, honoring those who have passed. You can also email photos to pics@KillerMargaritas.com by October 25th, and Cesar’s will include them in the display. Celebrate Halloween and Día de los Muertos with family, flavors, and remembrance at Cesar’s!

spooky movie trivia all month long at lost never found

Every Wednesday at 7 pm

Lost Never Found is hosting a series of spooky-themed trivia nights every Wednesday in October, perfect for getting into the Halloween spirit! It all starts with Twilight Trivia Night on October 2nd, followed by Stranger Things Trivia on October 9th, and Rocky Horror Picture Show Trivia on October 16th. The fun continues with What We Do in the Shadows Trivia on October 23rd, and wrapping up the month is Buffy the Vampire Slayer Trivia on October 30th. Each night kicks off at 7:00 PM with prizes and specials!

lost never found pumpkin paint & sip

Every Thursday from 6-8 pm

Get ready for a night of fall fun and creativity at the Pumpkin Paint & Sip every Thursday in October, from 6:00 PM to 8:00 PM! For $35 per person, attendees will receive their own pumpkin to paint and take home, along with all the essential supplies—paint, glitter, brushes, and aprons. To add a little extra sparkle to the evening, guests will also enjoy a complimentary glass of champagne. The event, led by artist Dana Phipps, is perfect for anyone looking to celebrate the season with a creative twist. This 21+ event will have food and drinks available for purchase, making it a festive, fun-filled evening for all.

Halloween comedy night

Thursday, October 24 at 7 pm

Come out to Good Times Brewing for a night of comedy, drinks, and food! There are five comedians, and the show is free to attend. Help yourself to a $10 pizza slice and beer combo while you’re there, and come in costume for extra fun!

scary movie trivia

Thursday, October 24 at 7:30 pm

Do you like scary movies? Head over to Brickhouse Tavern for scary movie trivia, and enjoy some great specials while there!

Spooky Jazz and Boozy Boos

Halloween Adult Jazz Dance Class
Join Dance on Broadway for their annual Spooky Jazz and Boozy Boos! From 6:00-7:00 there will be a Halloween Themed Beg/Int Jazz class led by Marissa Shanbrom followed by a wine tasting brought to you by Bottles Up from 7:15-7:45! Get ready for the spookiest Jazz class of the year! Price includes dance class and wine tasting! This is a 21+ event.

Fall Cocktail Class at Big Star Wrigleyville

Thursday, October 24th from 7-9 pm

Celebrate the flavors of fall by learning to craft delicious autumn-inspired cocktails with Big Star! In addition to mixing up seasonal drinks, you’ll enjoy a hands-on experience at our build-your-own guacamole station, where you can create and snack on Big Star’s signature guac while mastering your cocktail-making skills.

Golden Autumn Margarita: Pueblo Viejo, Aronia Apologue, Apple Cider, Habanero Bitters, Lime

Season’s Harvest Whiskey Sour: Evan Williams Bonded, Apple Brandy, Honey, Apologue Persimmon, Lime

halloween group bike ride

Saturday, October 26th at 5:30 pm

Johnny Sprockets is hosting an exciting night ride on Saturday, October 26! They will kick off from 5434 N Clark at 5:30 PM, heading west and northwest before looping back south to the final destination at the Lakeview shop. The ride covers about 20 miles at a comfortable pace of 14-15 mph, but be prepared—some sections will be quite dark, so lights are required. After the ride, gather for drinks, snacks, raffles, prizes, and a spooky movie at the shop. Costumes are optional, but feel free to get creative!

Halloween Youth Party

Saturday, October 26th at 4PM

Dance on Broadway is so excited for our annual Fun Halloween Extravaganza on Saturday October 26th from 4:00-6:00pm featuring games, dance, and spooky activities such as a Costume Contest. This event costs $50 per dancer and is open to all dancers ages 4+ and includes the party and a pizza dinner! Please fill out the following questionnaire to help us accommodate your dancer’s needs at our party.

This is right after the Lakeview Chamber of Commerce: Little Monsters Crawl, so this would be a perfect opportunity for parents and dancers to celebrate Halloween in Lakeview all day long. RSVP Here

terrifying trivia – Halloween edition

October 30th from 7-9 pm

Test your Halloween knowledge at Terrifying Trivia: Halloween Edition on Wednesday October 30th at Lark Chicago! This spooky trivia night will challenge even the most dedicated horror fans with questions about all things Halloween—from classic horror films to eerie folklore. Grab your friends, get in the Halloween spirit, and enjoy a night of fun, competition, and themed drinks. Costumes are encouraged, so dress to impress and get ready for a frightfully good time!

halloween party

October 31st, 6:30 pm

Prizes, karaoke, beer, and more! What more could you want from a Halloween party? Good Times Brewing is throwing the ultimate Halloween Party and YOU are invited!

1920s Murder Mystery at the Speakeasy – Halloween Weekend

Saturday, November 2nd

TopAct Events invites you to an unforgettable evening of suspense, secrets, and mystery at Room 13, a Prohibition-era speakeasy at the Old Chicago Inn. Set in the 1920s, guests will dive into an interactive murder mystery, where the top crime boss has been killed, and it’s up to you to solve the case! Whether you’re a suspect, detective, or witness, the night promises thrilling twists and turns. Tickets include hors d’oeuvres, mystery materials, and prizes, while classic 1920s cocktails will be available for purchase. Don’t forget to dress in your best Roaring Twenties attire for the full experience!

spooktacular drag brunch at kit kat lounge

Saturday, October 12th and Sunday, October 13th

Celebrate Halloween early with the Spooktacular Drag Brunch at Kit Kat Lounge on Saturday and Sunday, October 12th & 13th! Join Shantell D’marco for hauntingly fabulous performances during one of three seatings at 10:30 AM, 1 PM, and 3:15 PM. Enjoy free-flowing mimosas and an unforgettable drag brunch experience as you get into the spooky spirit. Make your reservations at 3700 N Halsted for a brunch full of chills, thrills, and drag!

dressed to kill drag brunch

Saturday, October 12th

Join Lark for a killer good time at the Dressed to Kill Drag Brunch, starring the fierce Joan Julian! From 11:00 AM to 3:00 PM, enjoy bottomless drinks, including NÜTRL canned cocktails and $5 Bud Light, while indulging in fantastic drag performances. With a spooky twist and some seriously fierce vibes, this drag brunch is the perfect way to celebrate the Halloween season. Don’t miss your chance to be part of this unforgettable event—reserve your spot today!

a very wicked broadway brunch at kit kat lounge

Saturday, October 19th and Sunday October 20th

Join the Kit Kat Lounge & Supper Club for a spellbinding experience with their Wicked Broadway Brunch on October 19th and 20th! With three seatings available at 10:30 AM, 1 PM, and 3:15 PM, enjoy performances by the dazzling Shantell D’marco, hosted by the fabulous Angelicia Maria, featuring music from the hit musical Wicked and other Broadway favorites. Sip on free-flowing mimosas while indulging in a wickedly good time. Make your reservation today at Kit Kat Lounge, 3700 N Halsted, and don’t miss out on this magical brunch!

femme fatale drag brunch at kit kat lounge

Saturday, October 26th and Sunday October 27th

Get ready for the ultimate villain-themed brunch at Kit Kat Lounge with the Femme Fatale Drag Brunch on Saturday and Sunday, October 26th & 27th! Featuring Kinley Preston and Angelicia Maria, this brunch brings all your favorite femme fatale icons to life. With seatings at 10:30 AM, 1 PM, and 3:15 PM, enjoy free-flowing mimosas while you indulge in an unforgettable drag performance. Reserve your spot at 3700 N Halsted and get ready to brunch with the baddest ladies around!

the beetlejuice halloween drag brunch

Saturday, October 26th

Step into the spooky world of Beetlejuice at Lark Chicago’s Beetlejuice Halloween Drag Brunch on October 26th! Get ready for a thrilling and hilarious drag performance inspired by everyone’s favorite bio-exorcist. With fabulous queens bringing the spooky vibes and all your favorite Beetlejuice moments, this brunch promises fun, frights, and fantastic performances. Enjoy delicious food, themed cocktails, and an unforgettable Halloween-themed drag show. It’s showtime!

halloween weekend scaryoke

Friday, October 25th and Saturday, October 26th

Get ready for a spooky night of karaoke fun at Halloween Weekend Scaryoke on Friday and Saturday, October 25th and 26th! Hosted at Lark Chicago, this event is the perfect way to kick off Halloween weekend with your favorite songs and a hauntingly good time. Whether you want to belt out a spooky classic or just come for the entertainment, Scaryoke promises a night full of fun, festive vibes, and great drinks. Grab your costume and get ready to sing your heart out!

Oz Halloween Bash at Kit Kat Lounge

Thursday, October 31 
Head to Kit Kat Lounge for an unforgettable night in the Land of Oz! This Halloween, join Diva Kinley Preston for a fabulous evening filled with glitz, glamour, and all things Oz. Come dressed in your favorite costume for a chance to win $250 in cash and prizes. Sip on delicious cocktails, enjoy the dazzling performances, and immerse yourself in the Halloween magic. Don’t miss out on this enchanting night—follow the yellow brick road to Kit Kat Lounge!