Expert Picks

Your Weekly Guide for What to Do, See, Eat, and Drink in Chicago

Photo courtesy of Flight Club Chicago

This week in Chicago, celebrate Halloween by trick-or-treating in Lakeview, listening to scary stories at Otherworld Theatre Company, road-tripping to haunted houses and a new Indiana distillery, and dining at a West Loop restaurant “dressed up” as the Olive Garden.

Photo courtesy of 3 Floyds Brewpub

October 28: Trick-or-Treat on Southport 
One of Chicago’s most family-friendly neighborhoods puts on a great and safe trick-or-treating evening. Bop around from store to store, looking for candy and great deals. Each shop will offer something different, from a fun kids’ game to a discount on shopping to spooky kids’ meals. It’s a great night out. Details: 4–8 p.m. on North Southport Avenue, from Roscoe to Grace
—Samantha Lande, Family Fun

October 28: Scary Stories: Are You Afraid? 
Otherworld Theatre and Random Acts Chicago are teaming up for an evening of creepy short plays by a lineup of truly talented playwrights. I am so there!
—Tanuja Jagernauth, Theater

October 30: Devil’s Night at 3 Floyds Distilling 
3 Floyds’s new distillery, next to the brewpub in Munster, has gone even further toward the dark side with frightening decor flourishes. This round-trip tour leaves Lone Wolf on Randolph Street at 6 p.m., then stops for a bloodcurdling visit at Reaper’s Realm haunted house in Hammond, before landing at 3 Floyds to partake in its array of spirits and cocktails. Details:  6–11 p.m.; $45
—Jim Morris, Beer

Photo courtesy of Volumes Bookcafe

October 30: All-Women’s Open Mic and Showcase 
It’s hard out here for ladies living in a white supremacist, late-stage capitalist patriarchy. Enjoy the cozy atmosphere of Volumes Bookcafe and hear real-life stories from badass women making it work.
—Tanuja Jagernauth, Theater

October 31: Flight Club Embraces the 1893 Chicago World’s Fair 
Thanks to the wild popularity of Devil in the White City, the 1893 Chicago World’s Fair is an aptly popular theme for Halloween hoopla. This year, Flight Club is embracing the theatrical/morbid era with a Halloween event filled with fortune-tellers, magicians, and murder mysteries. Be sure to dress in theme for a chance to win the costume contest. And come hungry for chicken skewers, flatbreads, and pumpkin spice cotton candy. Details: 8–11 p.m.; $49
—Matt Kirouac, Food/Beverage

October 31: Dino S’mores Release Party 
Off Color is making the move from bottles to cans, and apparently Dino S’mores, its imperial stout that subtly and delightfully resembles the popular campfire dessert, is no exception. This Halloween-night beer-release party will feature a costume contest, as well as a Dino S’mores vertical on tap and other variants, including Chixculub (aka spicy s’mores). Details: 6–11 p.m.
—Jim Morris, Beer

Photo by Jeremy Farmer/Courtesy of Off Color Brewing

Through November 1: Saint Lou’s Assembly Dresses Up as Olive Garden 
Here’s a fun one: Saint Lou’s Assembly is embracing its inner Italian-American chain and slinging endless breadsticks for a few days this month. The decor will feature fake ivy plants, idyllic photos of the Italian countryside, and all the Frank Sinatra–style tunes you can dream of. To eat, the menu will boast fried ravioli, calamari, minestrone, tiramisu, breadsticks aplenty, and drinks like a frozen peach Be-Lou-ni and the Auntie Pasta Bloody Mary.
—Matt Kirouac, Food/Beverage

November 2: Sebastian Maniscalco: You Bother Me Tour at the United Center 
Maniscalco has been experiencing mass success over the past several years, and this year he landed himself at number five on the Forbes list of highest-earning stand-up comedians. His most recent Netflix special, ​Stay Hungry​, was a huge hit, as was his bestselling memoir. Not many comedians rise to the level of performing in arenas, but Maniscalco has been doing it for years. Details: 9 p.m.; $39–$250
—Matty Ryan, Comedy

November 2: “Restrain” at Monique Meloche 
Chicago choreographer Brendan Fernandes is having quite a year, with inclusion in the Whitney Biennial on top of multiple exhibitions that illustrate his interest in the power dynamics of ballet. He returns to Chicago with a solo show at this esteemed gallery. Not much info has been released yet, but considering how he weaves traditional dance with rope bondage and leather culture, expect it to be kinky.
—Claire Voon, Art

November 3: “The International Boutique for Middle-Aged Ladies” at Goldfinch 
Guest-curated by Chicago painter Mari Eastman, this group exhibition is also a shopping experience. Intended to replicate a boutique for women, the show will include sophisticated works like painted wallpaper and evocative perfumes.
—Claire Voon, Art

Through November 3: Brick or Treat at Legoland 
Spend a day before Halloween at this brick-tacular event. It’s always fun to be at Legoland, but especially during Halloween, when you’ll see the creepiest of Lego displays and meet Lego characters in the holiday spirit. It’s all the Lego fun you could imagine, Halloween-ified. Details: $17.95 and up
—Samantha Lande, Family Fun

Restaurant Opening of the Week: JIAO
Last fall, I embarked on a little dumpling crawl through Chinatown with some friends, and the versions we gorged on at Qing Xiang Yuan Dumplings were by far our favorites. So it’s with much excitement that the dexterous minds behind those doughy delights have expanded into the Loop with JIAO, a fast-casual option in sleek digs serving steamed and pan-fried dumplings like lamb and coriander, truffled beef, and shrimp-pork-leek.
—Matt Kirouac, Food/Beverage