West Town Halloween Food, Drink, and Parties 2026

Features waived bar covers, drink specials, and a costume contest.

Illustration of costumed clay figures with frothy beer mugs and glowing jack-o'-lanterns at picnic tables in a night patio (West Town Halloween Crawl)

West Town Halloween Crawl

Host-guided bar crawl visiting four establishments with an included shot

Illustration of a Halloween nightclub where costumed clay partygoers dance beneath purple and green lights near a stage (Haunted Halloween Ball 2026)

Haunted Halloween Ball 2026

Chicago's longest-running Halloween costume party in a historic haunted hotel.

Chicago Halloween Bar Crawl

Oct 24 – Oct 31

Halloween bar crawl visiting top Chicago bars with waived cover charges.

Memento Mori Halloween Gala

Fri, Oct 30

Chicago

Haunting Halloween fundraiser inside a historic medical museum mansion.

The Boos & Booze Chicago Halloween Bar Crawl | West Loop

Oct 30 – Oct 31

Two-day Halloween bar crawl through Chicago's West Loop neighborhood.

Ivy+ Alumni Chicago Halloween/Oktoberfest Costume Party

Thu, Oct 29

Chicago Free

Joint costume party bringing together alumni from eleven Ivy+ university clubs.

Illustration of costumed characters toasting with frothy mugs at picnic tables under string lights and pumpkins (Wrigleyville Halloween Crawl)

Wrigleyville Halloween Crawl

Features dinner buffets, gift cards, and a social media costume contest.

Illustration of a Halloween costume contest on an outdoor stage with costumed figures, a ghost, a trophy and a watching crowd (Shedd Aquarium Haunted House Party)

Shedd Aquarium Haunted House Party

A 21+ Halloween party blending house music DJs with aquarium exhibits.

The Boos & Booze Chicago Halloween Bar Crawl

Oct 30 – Oct 31

Two-day River North bar crawl with drink specials and after-party entry.

Illustration of costumed characters toasting with frothy mugs at picnic tables under string lights and pumpkins (Halloween Day Crawl in River North)

Halloween Day Crawl in River North

Daytime Halloween bar crawl with welcome shots and costume contests.

Illustration of costumed characters dancing at a Halloween party with pumpkins, a cake and a disco ball (R&B Halloween Costume Yacht Party Chicago on Anita Dee II)

R&B Halloween Costume Yacht Party Chicago on Anita Dee II

Three-level Lake Michigan cruise with DJ sets and skyline views.

Illustration of clay figures in costumes and a floating ghost at a Halloween party with a punch bowl and glowing pumpkins (Halloween on the Pier at Offshore Rooftop)

Halloween on the Pier at Offshore Rooftop

Fri, Oct 30

Chicago

Rooftop Halloween party with live house and EDM DJs.

Illustration of a cozy lantern lit patio at night where costumed figures toast frothy beer mugs at wooden picnic tables (West Loop Halloween Bar Crawl)

West Loop Halloween Bar Crawl

Multi-venue neighborhood bar crawl featuring drink specials and a costume contest

Illustration of a vampire bartender pouring a glowing green cocktail at a smoky Halloween bar with pumpkins and candles (Haunted Halloween Night Lake Cruise)

Haunted Halloween Night Lake Cruise

Fri, Oct 30

Three-story Lake Michigan yacht party with a live DJ.

Illustration of a glowing Halloween party scene with a pumpkin, a witch figure, a cat and a cake on a purple dance floor (Local Edition Fall Night Market)

Local Edition Fall Night Market

Thu, Oct 8

Curated evening market featuring small-batch goods and live music.

WIOFA Presents All Hallows' Evening 2

Chicago

Charity Halloween party benefiting pediatric cancer and blood disorder patients.

Illustration of costumed figures beside a table with two gold trophies on a hay covered stage with pumpkins and string lights (Afrobeats Fridayz Halloween Costume Party)

Afrobeats Fridayz Halloween Costume Party

Oct 30 – Oct 31

Costume party featuring Afrobeats, Amapiano, and up to $1000 in prizes.

Offshore Halloween

Rooftop party featuring live DJs and sweeping Lake Michigan views.

Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights (2026 HALLOWEEN BOO BASH)

2026 HALLOWEEN BOO BASH

Sun, Oct 25

Chicago 6 mi $$

Costumed Halloween fundraiser featuring karaoke, campfire stories, and trick-or-treating in the theater.

Illustration of a glowing Halloween party where a vampire and a girl stand by a pumpkin disco ball near a cake and a cat (Monster Mall Chicago: Boo's and Brews)

Monster Mall Chicago: Boo's and Brews

Sun, Sep 20

Chicago Free

Spooky pop-up market featuring alternative vendors, treats, brews, and music.

Illustration of a Halloween costume contest on a decorated barn stage with ghosts, a trophy table and pumpkins in front (Afrobeats Saturdayz: Halloween Costume Party)

Afrobeats Saturdayz: Halloween Costume Party

Features a costume contest with up to $1,000 in prizes.

Haunted Harbor

CHICAGO Free

Open-air lakefront electronic music event featuring DJs, fog, and spooky visuals.

Haunted Mansion (Sunset Society)

Multi-floor Halloween electronic music party with 16 DJs in Logan Square

Illustration of a candlelit Halloween dinner table with small pumpkins, black cauldron bowls and a friendly ghost nearby (Hands-On Pumpkin Ravioli Making Class)

Hands-On Pumpkin Ravioli Making Class

Make fresh pasta dough and pumpkin ricotta filling from scratch.

Illustration of a pumpkin headed clay performer in a purple feathered costume on a stage as a costumed crowd cheers (Twisted Horrors: A Femme Halloween Soiree)

Twisted Horrors: A Femme Halloween Soiree

Femme Halloween gathering featuring live pole and burlesque performances.

Illustration of a Halloween nightclub stage with a performer in a purple feathered costume, curtains, fog and pumpkins (Dark Paradise: Halloween Bash)

Dark Paradise: Halloween Bash

A 21-and-over Halloween celebration featuring music, costumes, and themed decor.

Illustration of a Halloween costume contest on a small stage with a pumpkin, robot, witch, ghosts, trophy and audience (Pink Peach Events Presents: Trick or Turn Up — Hip-Hop & R&B Halloween Party)

Pink Peach Events Presents: Trick or Turn Up — Hip-Hop & R&B Halloween Party

Cicero 6 mi $$

Features a DJ dance floor, costume contest, and photo booth.

Illustration of a Halloween party at dusk with a ghost above string lights, two witches by a table, and glowing pumpkins (Fall Bakes: Fall Themed Baking Class)

Fall Bakes: Fall Themed Baking Class

Hands-on instruction for pumpkin scones and caramel apple pull-apart bread.

Pumpkin Carving Party at Federales

Mon, Oct 26

Includes a pumpkin, carving kit, and a select margarita.

Illustration of a Halloween costume contest on a small stage with a pumpkin, robot, witch, ghosts, trophy and audience (Halloween Comedy Bash: Laugh Till You Scream)

Halloween Comedy Bash: Laugh Till You Scream

Live comedy showcase, costume contest, vendors, and poetry performances.

Illustration of small costumed figures toasting with a frothy mug beside wooden barrels, pumpkins and autumn trees outdoors (Fallin’ for Wisconsin)

Fallin’ for Wisconsin

Day trip from Chicago featuring wine tasting, apple picking, and Lake Geneva.

Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights (Afternoon Tea: Fall Edition)

Afternoon Tea: Fall Edition

Fall-inspired teas, herbal infusions, and family-style treats.

Illustration of clay figures clinking foamy beer steins at wooden tables under a striped tent with pretzels and pumpkins (Y2K & 16 Candles Live at St. Al's Oktoberfest)

Y2K & 16 Candles Live at St. Al's Oktoberfest

Chicago Free

Live music spanning three decades on the Southport Main Stage.

Oktoberfest

Sep 25 – Sep 26

Woodridge 23 mi $$

Adults-only festival featuring live music, German food, and beer.

Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights (Autumn Reserve Wine Experience)

Autumn Reserve Wine Experience

Thu, Oct 15

Lisle 22 mi $$$

Fine wine tasting and live guitar amidst changing autumn leaves.

Illustration of costumed clay characters toasting with frothy mugs at an autumn festival tent among barrels and pumpkins (Ciderfest 2026: A Seasonal Cider Celebration)

Ciderfest 2026: A Seasonal Cider Celebration

Thu, Sep 24

Cider tastings with a commemorative glass and dog-friendly admission.

Illustration of a Halloween party at dusk with a ghost above string lights, two witches by a table, and glowing pumpkins (An Oktoberfest Celebration)

An Oktoberfest Celebration

Thu, Oct 8

Lombard 17 mi Free

Business networking gathering featuring pretzels, brews, and professional connections.

Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights (ISBS Oktoberfest Open House)

ISBS Oktoberfest Open House

Fri, Oct 23

Lombard 17 mi Free

Casual open-house networking event with complimentary food, drinks, and prize giveaways.

The Nightmare Bar

Tim Burton and horror movie-inspired Halloween bar

Illustration of costumed clay characters toasting with frothy mugs near barrels and pumpkins at an autumn beer festival (Lincoln Park Wine Fest)

Lincoln Park Wine Fest