Haunted Happenings in Lakeview East

Halloween isn’t just a date on the calendar; it’s a state of mind, a festival of the bizarre, and a celebration of all things spooky. It’s that bewitching time of year again – the season of Halloween! Unleash your inner horror obsessed self, que up the scary movies, and prepare yourself for a season of fright. Read on how to discover the best LVE has to offer to savor the season of the witch. 🎃👻🕷️

The events listed are in order by date! For things happening on Halloween (October 31) scroll to the middle of the page.


Month Long Events

Nightmare on Clark Street

Chicago’s favorite annual Halloween-themed extravaganza is back for the 2025 season starting October 10th! Step inside Nightmare on Clark Street, where spooky season takes over Stolen Saddle! Enjoy over-the-top haunted décor, creepy-themed cocktails, and Instagram-worthy photo ops designed to get you into the Halloween spirit! Happy haunting.

boo-kini bottom

I’m ready! I’m ready! I’m ready! Replay Lincoln Park has done it again, they have transformed every square inch of their huge arcade bar into an astonishing pop-up. Just in time for spooky season, get lost in the underwaters of Boo-Kini Bottom! Inspired by everyone’s favorite crew under the sea, this fully themed experience takes you deep into an ocean of cocktails, events, and Halloween fun. Expect all-new themed cocktails, over-the-top décor, new trivia dates, and special events every week. And for Halloween? Get ready for one of the biggest costume contests in the city with some of the best prizes in Chicago. Whether you’re here to sip, snap, or sea the magic, this is your chance to experience Bookini Bottom before it floats away at the end of October.

No reservations needed, just swim on in!

Haunted Happenings

Pole dance, flow arts, and burlesque, oh my! On Sunday, October 12th from 7 to 9 pm, be amazed at the Newport Theater for their Fae Soiree: Halloween Edition. This enchanting, whimsical, and sensual burlesque show created and hosted by Gaybriel Le Fae.

Enter if you dare! Bring your tipping dollars.

Annual Horror Marathon | All Month Long

In celebration of spooky season, Alamo Drafthouse in Wrigleyville be showing old school horror movies all October long! With classics like CREEPSHOW (1982), Scream (1996) and The Mummy, you can catch Halloween favorites on the big screen.

spooktacular drag brunch | October 18 & 19

The newly opened Kit Kat Club is hosting a Spooktacular Drag Brunch on both Saturday October 18th and Sunday October 19th, hosted by Shantell DeMarco & Abigale Beverly Hillz! Seatings are at 11 am and 1:30 pm! Book your seats online through OpenTable, call (773) 525-1111 to reserve, or buy a ticket in advance.

Tickets Include: Two course prix fixe brunch with entree choice, free flowing brunch drinks: Mimosas, Bellinis, Sangria, Bloody Mary Martinis, 1800 Tequila Skinny Margaritas, Vodka Spritzers, and a 2 hour seating.

Pumpkin Paint & Sip | October 9, 23, and 30

Pumpkin Painting | Every Wednesday in October

Pumpkin Painting | Every friday in October

terrifying trivia | october 22 & 29

Spooktacular Haunted Trail | October 23, 24, 25, 26, 30, 31 and Nov 1 & 2

frankenstein | October 24-26

Rocky Horror Picture Show 50th Anniversary Spooktacular! | October 25, 6:30 to 8:30 pm

Halloween Brunch | October 26th

scary-oke | October 29

Are you scary good at singing, or does your singing scare people away? Rock the Tin Roof stage on October 29th for karaoke- Halloween edition!

journeymen tasting spooktacular | october 30th

Space Park, located at 815 W Roscoe, is turning into a Haunted Trail for Halloween! During the haunted trail on Hallows Eve, Journeyman Distillery will be hosting a tasting of some delicious brews. Sample Featherbone Bourbon, Last Feather Rye Corets, Whips & Honey, and OCG Apple Cider Liqueur. Also in attendance will be Screamin’ Rachael from Trax Records! Grab a ticket now!

Halloween Events – October 31

Wrigleyville Halloween Crawl

On Friday, 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!

WHAT’S INCLUDED: Tickets include admission, free dinner buffets, gift cards to use on the crawl, costume contest, giveaways and more!

WHERE: Wrigleyville’s Best Bars* including: Old Crow, Moe’s, HVAC, Cubby Bear, Murphy’s, Stretch, Roadhouse 66, Country Club, Rabbit Hole, Sports Corner, Underground Lounge, DraftKings, Almost Home Tavern, Lucky Strike, Yak-Zies, Tin Roof, Stolen Saddle, Sluggers, Rizzo’s, Merkle’s, Home Away From Home, Cheesie’s, Vines, Pilot Project Brewing, Trace, Smoke Daddy, Graystone Tavern, Bernie’s, Dugout & More TBA! *Bars subject to change

Haunted Halsted Halloween Parade

The 28th annual Haunted Halsted Halloween Parade, October 31st, 2025 in Chicago’s landmark LGBTQ Northalsted neighborhood, hosted by the Northalsted Business Alliance!

The free-to-watch parade, ranked one of the top ten in the US by Fodor’s Travel, has a spectacular Costume Contest with hundreds of entrants (Sign Up Free) featuring $4,000 in cash prizes and concludes with an awards presentation.

The Parade also features the Chicago Full Moon Jam fire performers, Windy City Jeep Club, Chicago Thriller, Lakeside Pride Marching Band, The Windy City Rollers, and Chicago Spirit Brigade pep squad.

The costume competition covers 5 categories: Character, Creative, Scary, Youth (<13) and Group. Each category will have a $500/$200/$100 prize winner for 1st place/2nd place/3rd place, respectively.

ghouls night out | trace chicago

Wrigleyville’s spookiest Halloween party is back! Join Trace Chicago on Halloween from 5 PM to Midnight for the 4th Annual Ghouls Night Out—a haunted celebration packed with costume contests, cash prizes, creepy games, and more.

Whether you’re rocking something sexy, scary, or just straight-up weird, you’ll want to enter the Halloween costume contest for a chance to win cold, hard cash. Plus, enjoy classic party games like bobbing for apples, themed drink specials, and plenty of tricks and treats all night long.

Come dressed to distress… if you dare. No reservation or tickets necessary, just show up!

The Monster diner | celebrating lady gaga from 6 to 10 pm

The Chicago Diner Lakeview is calling all the little monsters to celebrate Lady Gaga in the heart of the Haunted on Halsted parade!

THE Halloween Extravaganza Drag Dinner

Come join the boo-tiful Kit Kat divas on Halloween night! THE Halloween Extravaganza Drag Dinner featuring Kinley Preston, Shantell Demaco, & Kylee Hunter. Book your seats online through OpenTable, call (773) 525-1111 to reserve, or buy a ticket in advance. Tickets Include a starter, your choice of entree, two martinis, and a 2 hour seating. Seatings are at 6 pm and 8 pm!

barcocina circus

Step right up! Barcocina is throwing a circus on Halloween night. A $50 ticket will get you three hours of bottomless drinks (Beer, Seltzers, House Cocktails (Vodka Soda, Whiskey Coke, etc.), House Margarita, Skinny Punch.) , and you can watch aerialists, fire dancers, and more. The party is from 10 pm to 1 am. Reserve a VIP fire pit for any group size! Email Desi@barcocinachicago.com

spooktacular drag brunch

Start your Halloween season with a bang (and free-flowing mimosas, Bellinis, Sangria, Bloddy Mary Martinis, Skinny Margaritas, and Vodka Spritzer). The Spooktacular Drag Brunch ($72.49 per person +Tax and gratuity; -$10 if not drinking) features electrifying performances by Shantell D’Marco and Abigail Beverly Hillz , bringing their signature blend of glamour, wit, and fierce vocals to the Kit Kat stage. Guests can indulge in the club’s new fall-inspired brunch menu and sip from an array of over-the-top cocktails—all while surrounded by hauntingly chic Halloween décor. No cover. See menu.

KILLER LOOKS

The Colette Collection

Colette cuties know that The Colette Collection is THE neighborhood boutique for trendy looks for any holiday / season! Stay warm in a bootiful sweater, get Halloween accessories, and browse the clearance rack while you’re there!

goldplaited boutique

Goldplaited has been waiting for Spooky Season to debut their huge Halloween collection! Come on down to this stylish boutique and treat yourself to something cute enough to wear all year.

TURN YOUR HOME INTO A HAUNTED HOUSE

Foursided

Gourd vibes only at Foursided! From horror themed coffee table books, black flame candles, and literally ALL things pumpkin, Foursided has everything you need to transform your space into a monster getaway. With two Lakeview locations, come stock up and be the talk of the ghost town.

plant stand collective

Plant Stand Collective has some killer plants for sale! They carry so many carnivorous plants, and also black and orange pots for them to live in. Don’t be scared to add some spooky plants to your collection! The Plant Stand Collective crew will help you find the perfect plant so it doesn’t end up in the graveyard.

SCARY GOOD TREATS

windy city sweets

Sweet so good you don’t mind killing your diet this Halloween. Windy City Sweets has all your fall favorites- like caramel apples, any candy you can name, and even cute chocolate goods like these white fudge mummy oreos!

ROCKS | Slasher Burger Available All October Long

The Slasher Burger is so good you’ll scream. An 8oz smash patty with mac and cheese, diced jalapenos, cajun shoestring fries, drizzled with chipotle BBQ and siracha and served on a brioche bun and brushed with roasted garlic aioli. Just $17.75 to satisfy your taste buds, and available all month long at ROCKS.

Matilda + babyatlas

Matilda is serving up Halloween themed cocktails and dishes this spooky season. They also have Trivia Tuesday every week, where you can put your brain to the test while enjoying these October specials!