Spooky Season in Lakeview East
This fall, Lakeview East is creepin it real. Our neighborhood goes all out for just about everything, and Halloween is no exception. Halloween isn’t just a day, it’s the entire month in Chicago’s most extravagant neighborhood. Scroll below to see every Halloween / Haunted Event happening this Spooktober, separated from week to week. Stay scary Chicago!
Nightmare on Clark Street
Open from October 10th to November 1st At Stolen Saddle
The rooftop of Stolen Saddle is turning into something straight out of a nightmare, for three weeks this fall. Nightmare on Clark Street is making it’s return from the dead, with over-the-top Halloween décor, themed rooms, festive cocktails, and plenty of photo ops. Every ticket includes a drink!
twilight pop-up bar
Opening October 9th at Replay Lincoln Park
Bella, where have you been loca? Launching Friday, October 9, Replay Lincoln Park is hosting a brand-new Twilight pop-up, bringing the eerie town of Forks to Chicago with immersive recreations of classic scenes, photo ops with your favorite characters, iconic meme references, themed details, and plenty of moments made for your camera roll.
Replay Lincoln Park hosts the most iconic pop-ups in Chicago, with thousands of decorations, delicious themed drinks, and tons of fun events. Whether you’re Team Edward, Team Jacob, or just here for the baseball scene and the memes, come spend Halloween season in Forks at Replay
Keep Up on Events at Replay’s Website
October 1-4
The addams family drag dinners
Friday, October 2 and Saturday, October 3 | 6 pm to 10 pm
Abigail Beverly Hillz, Joan Jullian, and Jacky Couture are hosting The Addams Family Drag Dinners on Friday and Saturday night! Your tickets don’t just include a scary good show, they also include a prix fixe dinner, with a starter, choice of entree, and two martinis!
American Horror Stories Bottomless Drag Brunch at LARK
Saturday, October 3 and Sunday, October 4 | 11 am to 3 pm
Kick off October with an American Horror Story themed Brunch at Lark! The hauntingly beautiful hosts Venus Carangi and Ginger Forest will be performing, with great costumes, fun music, all while you enjoy delicious food and bottomless drinks from Lark.
October 5-11
spooky trivia at lark: horror movies
Wednesday, October 7 | 7 to 9 pm
What’s your favorite scary movie? Lark is hosting Spooky Trivia on Wednesdays throughout October, with a different theme every week. This theme is Horror Movies! Specials for the evening are Double Cheeseburgers for $10, $5 Bud Light, and $8 on all mules.
raks inferno Halloween circus burlesque
Friday October 9 | 7 at Newport Theater
This Halloween, experience a burlesque circus speakeasy featuring performers who headline international festivals! “Spectacular!” – WGN-TV
“Best of Chicago” 2025 Winner – Chicago Reader
Experience a spooky cabaret with burlesque performers, fusion bellydancers, circus artists, and more! Join Raks Inferno for a unique show featuring artists who have performed around the world, dazzling and inspiring audiences from Germany to Morocco, Costa Rica to the Czech Republic.
Featuring:
Miss Nyxon, Duchess of Tease 2025 (NOLA), fresh off the Burlesque Hall of Fame stage
Caity, award-winning pole artist and contortionist
Lee Na-Moo, who’s toured Europe with Bellydance Evolution
Dawn Xiana Moon, who has sung the National Anthem for the Chicago Bulls and danced on Britain’s Got Talent
and more!
Get Tickets Here
The Dead Dance Bottomless Drag Brunch
Saturday, October 10 and Sunday, October 11
11 am to 3:30 pm both days
Kit Kat Club invites you to the Dead Dance Brunch, happening on both Saturday and Sunday! Kit Kat Divas Abigail Beverly Hillz and Joan Jullian will be your hosts for the brunch. Tickets include a two-course prix fixe brunch with an entree choice, with free flowing brunch and a two hour seating.
Get tickets here
zombie Bottomless Drag Brunch
Saturday, October 10 and Sunday, October 11
11am to 3pm both days
Head to Lark over the weekend for Zombie Drag Queen Bottomless Brunch with hosts Apollo Summers & Venus Carangi! Each ticket guarantees the guest’s seat and serves as their reservation, with all tickets including the bottomless brunch package.
killer prom at replay lincoln park
Saturday, October 10 at 9 pm
Got the looks that kill? Replay Lincoln Park is hosting Killer Prom on Saturday night, a dark, over-the-top prom night with music, drinks, dancing, and a contest built for anyone who wants to go all in on the look! So yes, this is your excuse to show up dressed like the main character, hit the dance floor, and make it count
21+ and no cover
spooky arts and crafts
Saturday, October 10 from 3 – 4:30 pm, at Shine Bright in Life
October’s Arts & Crafts class invites participants to get into the spooky spirit with an inspirational idea buffet filled with creative projects to explore. With a variety of spooky-inspired activities to choose from, attendees can follow their interests and create something uniquely their own.
The featured project is spooky glass painting, where participants can choose from a variety of spooky coloring pages, trace their favorite design onto glass, and bring it to life with paint. With plenty of projects and creative options to explore, the class offers something for every experience level and is a fun opportunity to play, create, and make a little spooky magic.
October 12-18
spooky trivia at lark: twilight trivia
Wednesday, October 14 | 7 to 9 pm at Lark
Whether your team Edward or Jacob, all are invited to play Twilight Trivia! Lark is hosting Spooky Trivia on Wednesdays throughout October, with a different theme every week. This theme is Twilight! Specials for the evening are Double Cheeseburgers for $10, $5 Bud Light, and $8 on all mules.
the rocky horror picture show trivia
Thursday, October 15 | 7 to 9 pm at Replay Lincoln Park
Give yourself over to absolute pleasure at Rocky Horror Picture Show Trivia at Replay Lincoln Park! For Halloween season, Replay is transforming into a Twilight pop-up, and is hosting fun Halloween themed events like this, all month long. Trivia is free to play, there are prizes for the top teams, and tons of fun to have!
Pumpkin Bowling at duffy’s
Thursday, October 15 | Sign Ups Start at 7 pm
Pumpkin Bowling is a thing, and it’s happening at Duffy’s Tavern on Diversey on Thursday, October 15th! Sign-in starts at 7 pm, and bowking starts at 7:30 pm. The grand prize is a pair of Blackhawks tickets! There will be a prize for best costume and best team name, so get creative and dressed to impress.
Sign Up Here
rpg-13: a spooky comedy show
Friday, October 16 | 7 pm at Newport Theater
Welcome to RPG-13, the comedy company from Chicago, IL, that combines role playing games with improvisation: where fate and funny collide! And we are celebrating the spooky season with several of our friends!
Join our Game Master, as they invite a volunteer from the audience onstage (maybe you!), and will help you create your very own role playing adventure! You will create your character, pick which Adventurer as your avatar, and discover the location and genre of your adventure. However, as the story unfolds, the random roll of the dice will be the deciding factor on how well everything goes. Roll a 20, a glorious success! Roll a 1, a hilarious disaster!
Get Tickets Here
ghosties themed paint party
Friday, October 16 | 7:30 pm at Shine Bright in Life
Once a month, community art center Shine Bright in Life, hosts a paint party with a theme! Paint Parties are a playful, no pressure night to unwind, experiment, and reconnect with your creativity. For October, the theme is Ghosties! Create something ghouling, or scary cute, to display proudly in your home. This isn’t paint-and-sip. It’s paint-and-play. Follow the theme, work on something of your own, or simply paint whatever calls to you. There are no wrong answers and no pressure to create a masterpiece. All materials provided. All experience levels welcome.
Register Here
Pints & pumpkins at pilot project wrigleyville
Sunday, October 18 | 11 am to 3 pm
A beautiful fall Sunday spent sipping beer and painting pumpkins?! Yes please! Pilot Project Brewing in Wrigleyville is hosting Pints & Pumpkins, and tickets are only $10! Price includes the pumpkin, carving tools, and a cider. Grab a ticket before it sells out!
Register Here
October 19-25
practical magic trivia night
Wednesday, October 21 | 7:30 pm
Budweiser Brickhouse Tavern in Wrigleyville is hosting a Practical Magic Trivia Night, with some great potions available. Sip on $12 margaritas, and enjoy Midnight Margaritas and Chocolate Cake! Prizes will be given to first, second, third place, AND best dressed will also get a reward!
Reserve a Table
witches b*tches & bingo
Wednesday, October 21 | 8 to 10 pm
Psycho bingo hosted by Diamond Yaki and Kev Rokken kicks off Wednesday October 21st and you better be ready! In addition to the usual chaos and standard prizes, come dressed to impress for a witch-themed costume contest for the cash grand prize.
pumpkin carving and dog costume contest
Thursday, October 22 | 7 pm
PUMPKINS. PUPS. PRIZES. The 9th Annual Pumpkin Carving & Dog Costume Contest is back at Replay Lakeview! Join them on Thursday, October 22 at 7PM for one of their favorite spooky-season traditions. Guests can grab a complimentary pumpkin and carving supplies with the purchase of a Sun Cruiser or Dogfish Head, while pups are invited to show off their Halloween best in the Dog Costume Contest. Prizes will be awarded to the top three in each category, with the festivities hosted by Alex Kay. Bring your pumpkin, bring your pup, and get ready for a night of Halloween fun!
spooky art fair
Friday, October 23 | 6 pm
Spooky season is getting an art night. Get a head start on your candy haul and swing by Replay Lincoln Park for free candy and creepy-cute finds. Local artists Pelon Creates, Natalia Sustaita, Squeak Starzula, and Raquel Hung are putting their spookiest art on display for one night only. Come browse, support local artists, grab a drink, and stick around for DJ Adam Black and a special Fall Out Boy tribute after 8 pm.
KIDS HALLOWEEN DANCE PARTY
Saturday, October 24 | 4 to 6 pm
Dance on Broadway is hosting a Halloween Dance Party the week before Halloween! From 4 to 6 pm, come dressed in your favorite costume and come dance, play games, and eat treats. Ages 3+ and registration is required
Register Here
Rocky horror picture show memorial watch party
Saturday, October 24 | 7 pm to 8:30 pm
Hop on over to Cuddle Bunny to celebrate the life of the entertaining and enigmatic Tim Curry with this cult classic during a lowkey, yet interactive, experience with bunnies! The Rocky Horror Picture Show is R-rated, so only adults are permitted. Attendees will receive a prop bag full of bunny-appropriate items and a list of cues for fun-filled audience participation. For the safety of the bunnies, no outside props will be allowed. Don your best Dr. Frank-N-Furter, costume to win a prize appropriate for such a spooktacular occasion! Festive snacks, popcorn and hot chocolate will be provided.
Get Tickets Here
howl-a-ween dog market and costume contest
Sunday, October 25 | 11 am to 2 pm
Stolen Saddle is teaming up with 312 Markets for a Howl-A-Ween party, and YES, your pup is invited! Come shop local vendors, enjoy Tito’s sampling from 11 am to 2 pm, and enter your pup in a Halloween costume at 1 pm. Top three costumes get prizes! $20 Bottomless Mimosas or Aperol Spritz, AND $35 Breakfast for the table!
halloween, october 31
Grave Rave at the river
9 pm to Midnight
The Halloween celebration is raising the dead and raising some hell with a night packed with fun. Guests can enjoy a DJ all night, go-go dancers, apple bobbing, specialty shots, an open bar, and walking apps throughout the evening. Costumes are highly encouraged, so guests are invited to get creative and embrace the Halloween spirit. Wristbands include well cocktails, domestic beers, High Noons, and walking apps all night. Early bird tickets are $20, with the next ticket tier priced at $40. Guests are encouraged to grab their crew, put together their best costumes, and get weird this Halloween.
the hot b!tch halloween party
Smartbar | Doors at 10 pm
Featuring Miss Toto * Madeline * Kitt Vesper * Virago
Hosted by Alex Jenny * Eliel * Kahmora Hall * Lezbian Minnelli * MizThang * Vanity Unfair
$20-$25 Adv / $25 Door / $20 Student Door (before 12am with valid ID) / 21+ /
Doors and entertainment at 10 pm.
wrigleyville halloween crawl
All over Wrigleyville, from 5 PM to 1 AM
On Saturday, October 31st, the historic Wrigleyville neighborhood will be full of party-seekers creeping and crawling from bar to bar on the only night where you can act like a kid and drink like an adult! You and your friends can show off your costumes as you sing, dance, and drink the night away. Throw on your best costume and join in on all of the frightening fun for this haunted holiday at the BIGGEST Halloween Party in Chicago!
Get Tickets Here
dolloween, halloween for the lesbians
Level Sporting Club | 7 pm – 1 am
This one’s for the dolls. Level Sporting Club is kicking off their first ever Halloween Party with Nina Doll House and Voly Red. There’s a costume contest at 9 pm with a cash prize, and dancing all night long! Let’s boogie.
Sounds By: Live DJs spinning Latinx hits, Hip-Hop, Reggaeton, and high-energy party anthems all night long
VIP & Table Service: Tables are extremely limited and will sell out fast. Table fee includes entry for 2 people and tables seat 4
Get Tickets Here
monster mash bash
Lark | 9:30 pm – 3 am
Halloween at Lark is one for the books this year. Jaharia from Dragula is hosting a night of freaky fun soundtracked by DJ Ricky Sixx. General admission is $15, and drink specials include Nutrl Drink Buckets and $5 Bud Lights. Come dressed as your best and you might have a chance to win the $100 cash prize in the costume contest.
Haunted Saloon
Charlie’s | 11 pm – 4 am
Strap on your cowboy boots and saddle up your skeleton horse because Charlie’s has been taken over by ghouls and ghosts! Drag queens from the underworld Fifi Depraved, Pixel, Luna La Catrina, Persephone Brooklyn LaRue, Sapphire Feliciano, and the hostess with the mostest, Bella DeBalle are coming back to life for one incredible spooktacular drag show.
At midnight, their annual costume contest returns with big cash prizes! Sign-ups are from 11-11:45 pm and prizes are as follows:
1st Place: $500 Cash
2nd Place: $250 Cash
3rd place: $100 Cash
