Hubbard Inn transforms into The Haunted Inn for 13 days this season. (Kaitlyn McQuaid / For RedEye )
Maybe it's the candy-induced sugar rush or the anonymity that masks offer, but Halloween is second only to New Years' Eve when it comes to no-holds-barred debauchery. For some, it's a chance to show off a killer homemade costume, while others are content to throw on a store-bought cape and hit the bars. Because this year's holiday falls on a Thursday, true die-hards can party twice; plenty of bars and clubs will throw parties the weekend before, and others plan big bashes for Oct. 31. Here's a toast to the one time each year when it's normal to wake up to a pillowcase covered in glitter and a set of cat ears on the bedroom floor. email@example.com | @redeyeeatdrink
Now through Nov. 1: The Haunted Inn at Hubbard Inn
110 W. Hubbard St. 312-222-1331
The River North bar and restaurant has slipped into a haunted hotel theme through the end of the month, with two floors of vintage hotel decor and themed cocktails ($13) such as Death in the Afternoon (absinthe and champagne) and Pumpkinn (gin, grapefruit and cinnamon syrup, and pumpkin pie syrup). Stick around for dinner with a three-course harvest menu ($31), which features dishes including seared scallops with pumpkin puree and sage-hazelnut brown butter; maple-glazed pork tenderloin; and a chicken crepinette with apple stuffing and cranberry mostarda. 11 a.m.-close. No cover.
Oct. 24: The Squidling Bros. Circus Sideshow at Live Wire Lounge
3394 N. Milwaukee Ave. 773-756-5363
Inspired by early 20th century circus sideshows, performers The Squidling Brothers have created a twisted, humorous and edgy show full of dancing, sword-swallowing, fire-breathing, body modifications, burlesque and more. The traveling troupe brings its oddities to this Irving Park bar for a mere $8, making this one of the most bizarre bangs for your buck this season. 10:30 p.m.
Oct. 26: The Numbered Days Halloween Loft Party at Logan Square Auditorium
2539 N. Kedzie Blvd. 773-252-6179
You, 500 costumed friends, candy and DJs. That's really all you need to know about The Numbered Days' bash, which kicks off with sets from three local DJs including Kyle Garner, Clash Gordon and Matt Roan. Come in your best, weirdest or coordinated group costume for a chance to win prizes, trick or treat via an "interactive candy installation" and don't forget bills for the cash bar. 9 p.m.-2 a.m. $20. Tickets: thenumbereddays.com
Oct. 26: The Belmont Burlesque at Theater Wit
1229 W. Belmont Ave.773-975-8150
The ladies of the Belmont Burlesque Revue plus special guests Serenna Starr, Helena Handbasket, Diva LaVida, Hazel Hellbender and Paly Flames present a spooky-sexy night of burlesque hosted by the vampiric MsPixy and her sidekick Giant Martini. Magic, comedy and plenty of sequins and fangs round out the performance. 10:45 p.m. $16. Tickets: theaterwit.org
Oct. 26: Nocturna All Hallow's Eve Ball at Metro
3730 N. Clark St. 773-549-4140
American Gothic Productions—the people who live every day like it's Halloween—goes all-out for a midnight dance party that lasts until the early hours of the morning. DJ Scary Lady Sarah spins a request-driven mix of current and classic goth, industrial, post-punk, death rock, ethereal, shoegaze and New Wave while you compete in a costume contest or show off in the Glitterguts photo booth. 11:59 p.m.-5 a.m. $15 with costume, $18 without.
Oct. 26: Whores of Horror 4: Slash-Her! at The Call
1547 W. Bryn Mawr Ave. 773-334-2525
Courtesy of Another Production Company, drag cabaret meets classic horror at this LGBT-friendly Andersonville bar with slasher-inspired acts from Ashley Morgan, Amanda Lynn, Coco Sho-Nell, Vivian Dujour and Muffy Fishbasket. $6 Absolut cocktails help you work up the courage to enter a costume contest following the show. 9 p.m. pre-show; 10 p.m. performance. $10.
Oct. 26: Halloween Costume Contest at The Boundary and Old Town Pour House
1932 W. Division St. 773-278-1919; 1419 N. Wells St. 312-477-2800
If you've worked for weeks on your costume, head to either of these two Bottleneck Management bars for a costume contest that could win you as much as $100. Video DJs play Halloween-themed songs and shows while guests vie to be one of the winners announced at midnight. 7 p.m. (The Boundary). 9 p.m. (Old Town Pour House). No cover.
Oct. 27-Oct. 31: Boo-ze! at Three Dots and a Dash
435 N. Clark St. 312-610-4220
Given the wall of blue-lit skulls that greet guests here, it shouldn't surprise anyone that the River North bar's first Halloween will be a special occasion. For five nights, Three Dots transforms into a creepy tropical lair serving seven special cocktails including Sidewinder's Fang (demerara rum, Jamaican rum, passionfruit juice, curacao and lime juice) and Pegleg Punch (vodka, aquavit, orgeat and grapefruit and lemon juices). Or, just order the Zombie Punch ($75, serves four to six), which is served in a seasonally appropriate crystal skull bowl. 5 p.m.-2 a.m. Sunday-Thursday. No cover.