Expert Picks

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

Photo courtesy of County Line Orchard

This week in Chicago, attend a pug party (seriously), go on an apple-fueled road trip, attend a pickling class, and take in a presidential theater production.

Photo courtesy of Maplewood Brewery & Distillery

October 14: 2nd Annual National Pug Day Party 
Maplewood might be the only place where you’d be thanked for saying, “Wow, your Fat Pug has a nice roasted, sweet chocolate taste. Really goes down smooth, too.” Well, on National Pug Day, the brewery will show you that it loves these little critters so much that it named its oatmeal stout after them. Maplewood is closing down the kitchen and calling all pug lovers and their better halves to the lounge to take a free professional dog portrait and raise money for a local animal rescue organization by just drinking beer. Say hi to Otto for me. Details:11 a.m.–11:59 p.m.
—Jim Morris, Beer

All Month Long: Go Apple Picking 
Check out our handy guide to apple picking. There are so many great places to get your apple fix (and if we are being honest, your cider and doughnut fix, too!), and it’s the best time of year to do it. If you’re lucky, you’ll be able to snag a few Honeycrisps as well!
—Samantha Lande, Family Fun

October 14: Chris Gethard: Half Life Tour at the Hideout 
Comedian, talk-show host, actor, and podcaster Gethard (​Broad City​, ​Career Suicide, The Chris Gethard Show​) has officially been doing stand-up comedy for half his life (he’s 40 and started at 20). To commemorate the milestone, he’s embarking on a tour where he’ll be performing stand-up and recording live episodes of his popular podcast, Beautiful/Anonymous.​ Both Hideout shows will be stand-up, with comic Carmen Christopher opening. Details: 7 p.m. and 9 p.m.; $25
—Matty Ryan, Comedy

Photo courtesy of City Winery at the Riverwalk

October 14: Picklin’ and Preserves Class at Ina Mae Tavern & Packaged Goods  
If you’re a fan of the delicious pickles and preserves at Wicker Park’s New Orleans–inspired Ina Mae Tavern, then definitely make sure to sign up for the fun class it has in store. The Picklin’ and Preserves class will teach attendees how to make Michigan apple jam, pickled peaches, berry preserves, and bread and butter pickles, and the class kicks off with welcome cocktails. Guests also get 15 percent off dinner either before or after the class. Details: 6:30 p.m.; $40
—Matt Kirouac, Food/Beverage

October 16: The City Winery River Domes Are Back  
For better or worse, one surefire sign that summer is over is the annual return of the River Domes at City Winery at the Riverwalk. Yeah, drinking wine “alfresco” in a translucent igloo is cool as hell, but it’s a little sad to grapple with the notion that winter isn’t far away. The heated domes are back in action October 16–November 30, great for groups determined to keep those patio vibes going strong. Reservations are available for two-and-a-half-hour increments, and domes can fit up to eight guests. Details: Through November 30; $85 per person, including a $60 food and beverage minimum
—Matt Kirouac, Food/Beverage

October 17: Am I Man Enough? 
Storyteller and former professor Ada Cheng is at it again with another round of her storytelling series. She and her band of renegade storytellers will be at the Center on Halsted. Join them and bring those tissues.
Tanuja Jagernauth, Theater

Five Presidents / Photo by Michael Brosilow/Courtesy of American Blues Theater

Through October 19: Five Presidents 
I almost want to see this just to remember that there was a time not so long ago when the United States had presidents who were presidential. Conservative were ruthless, yes, but they had some expertise with geopolitical issues. They took care to craft an image of warmth for their constituents. They knew how to wear a suit. Heck, they knew how to speak. In this show, American Blues Theater brings to life a moment when five former presidents were all in the same room at the same time prior to Richard Nixon’s memorial service. I’m dying to be a fly on that wall, and I know that writer Rick Cleveland (House of Cards, The West Wing) won’t let me down. Details: At American Blues Theater
—Tanuja Jagernauth, Theater

October 18–20: Jim Gaffigan: Secrets and Pies Tour at the Chicago Theatre 
One of the most popular and prolific comics working today, Gaffigan is already considered by many to be one of the all-time living greats. With 12 albums and two books under his belt (one of which spent months on the New York Times Best Seller’s List), Gaffigan is showing no signs of slowing down. Don’t be surprised if much of the material on his Secrets and Pies tour ends up on his 13th album in 2020. Details: Showtimes vary; $52–$69
—Matty Ryan, Comedy

October 19: Tour of Elmhurst College’s Chicago Imagist Collection at Elmhurst Art Museum 
Iconoclastic and now iconic, the Chicago Imagists carved out one of the most important chapters in the city’s art history. For a primer on their works, head to this special tour of the museum’s newly reinstalled Imagist collection, led by none other than Suellen Rocca—one of the artists who helped birth the movement.
—Claire Voon, Art

Photo by Mistey Nguyen/Courtesy of Gadabout

Restaurant Opening of the Week: Gadabout 
Globally inspired street food is the bill of fare at this stylish new Andersonville spot, from a husband-and-wife team of chefs with a pretty stacked résumé (e.g., Pacific Standard Time, Boka, Hopleaf, Yusho). The menu is one of the most exciting assortments I’ve seen all year, running the gamut from buffalo skate wing and elote tarts to chickpea fritters, smoked eggplant, and even a Disney World–inspired combo of churros and pineapple.
—Matt Kirouac, Food/Beverage