Eat This Now: 23 Fall Dishes and Drinks to Try in Chicago

Seize the season with pasta, pierogi — and pumpkin too
October 23, 2017
by Matt Kirouac

Chicago’s dynamic dining scene is filled with must-have dishes all year long. Settling into cooler weather, though, it’s an apt time to check out the city's buzzy newcomers, fresh hot spots and vibrant new menu items at old standbys. These are the 23 essential dishes (and drinks!) you need to check out in Chicago right now. 

Fried chicken sandwich at The Orbit Room
The duo behind the Leisure Activities group and Sportsman’s Club, Jeff Donahue and Wade McElroy, is at it again with a spiffed-up version of Avondale’s classic Orbit Room. While staying true to the soul of this neighborhood standby, the pair updated the design, drinks and food, with the aid of chef Mark Steuer. Among the new menu highlights is a deep-fried delight that belongs on everybody’s cold-weather eating itinerary. Succulent and crispy, fried chicken breasts come spicy or mild, with classic accompaniments of iceberg lettuce and mayo on a buttery brioche bun. 

2959 N. California Ave.; 773-588-8540

Sausages at Bohemian House
Though its Eastern European fare is always delicious, Bohemian House’s new menu is particularly cravable right now. Along with other shareable items like a 19-oz. Bavarian pretzel and a fish board, the restaurant has amped up its sausage selection. New options include chicken bratwurst with Gouda and house mustard, applewood-smoked beef kielbasa and a crispy pork fritter dog with paprika aïoli.  

11 W. Illinois St.; 312-955-0439

SqueezIt cans at Corridor Brewery & Provisions
Big news out of one of Chicago’s premiere craft beer spots: Corridor Brewery & Provisions, from the owner of nearby DryHop Brewers, is now packaging beer in 16-oz. cans, starting with SqueezIt, a double dry-hopped double IPA. This bracing quencher is available in four packs to go, and it marks Corridor’s two-year anniversary. Heads up: these unsurprisingly popular beers have already sold out, but Corridor plans on releasing new four packs monthly, so keep your eyes peeled. 

3446 N. Southport Ave.; 773-270-4272

Impossible Burger at Umami Burger
The meat-free, plant-based “Impossible Burger” is sweeping the Windy City, with the latest iteration descending upon both local locations of Umami Burger. In partnership with Impossible Foods, the mini-chain makes a juicy, savory burger containing two patties, caramelized onions, American cheese, miso-mustard, dill pickles, lettuce and tomato. 

Wicker Park: 1480 N. Milwaukee Ave.; 773-423-2005
West Loop: 945 W. Randolph St.; 312-226-9919

Coconut Charcoal Elixir at Fairgrounds Coffee & Tea
Fairgrounds Coffee & Tea, one of the buzziest new coffee shops, has partnered with Vosges Haut-Chocolat for what’s sure to be the most memorable beverage of the season. The jet-black sipper is made with coconut charcoal ash, fermented cocoa and coconut puree, all of which provide health benefits. It looks good on Instagram too. Available for a limited time this season, the elixirs are sold at both Fairgrounds locations.  

Bucktown: 1620 N. Milwaukee Ave.; 773-770-3444
Millennium Park : 12 S. Michigan Ave.; 312-448-9015

Tortellini at Royal Grocer & Co.
Farm-fresh and rigorously seasonal, Bucktown’s newest restaurant is an appropriate spot to taste autumn in all its glory. One such dish is chef Rob Shaner’s tortellini, a soulful bowl of roasted squash and brie-filled pasta flecked with Colonel Newsom’s country ham, Swiss chard, apple cider and spiced pepitas. 

2118 N. Damen Ave.; 773-904-7805

Pumpkin spiced cheesecake at Petit Margeaux
Although it might sound basic, this is one pumpkin-spiced confection you’re going to want. For starters, it’s cute and photogenic with a pumpkin-shaped shortbread cookie garnish. The cheesecake is also satiny-smooth, redolent of warm fall spices and glazed with a patina of salty caramel. 

11 E. Walton St.; 312-625-1324

Cauliflower at Clever Rabbit
While many restaurants beef up their menus this time of year, Clever Rabbit celebrates fall in another — equally delicious — way. The roasted cauliflower dish serves as a vessel for a kaleidoscope of pickled summer vegetables, extending the life of those vibrant, colorful provisions we clamor for during warmer months. It also features cauliflower puree, which is surprisingly creamy and rich. 

2015 W. Division St.; 773-697-8711

TACOlato at Parlor Pizza Bar
It’s hard to save room for dessert at Parlor Pizza Bar, considering how rich the pizzas are, but thanks to a lineup of sweet new menu items, you’ll want to try. TACOlatos (waffle shell tacos + gelato) at Parlor’s West Loop outpost feature scoops of various flavors, sauces and toppings. Choice options include Unicorn Dreams, a rainbow medley of birthday cake ice cream, gummy worms, fruity marshmallows, rainbow Airheads, blue raspberry sauce, whipped cream, confetti and sprinkles; and Gimme S’more, with Rocky Road ice cream, chocolate chunks, marshmallow fluff, graham cracker, fudge sauce, whipped cream and a double chocolate shell. 

108 N. Green St.; 312-600-6090

Spiced butternut squash cheesecake at 312 Chicago
With its butternut squash, cinnamon, nutmeg, bourbon cream and walnut crust, the newest dessert at 312 Chicago reads like a hit list of fall’s favorite flavors. The handiwork of newly appointed executive sous chef Nick Blakey, the cheesecake is more delicate than typical New York-style. It's scented with autumnal spices and capped with candied walnuts before being garnished with vanilla-bourbon cream and butternut squash brittle for some  sweet crunch. 

136 N. LaSalle St.; 312-696-2420

Apple empanadas at Cafe Ba-Ba-Reeba!
Chicago’s O.G. tapas restaurant has a new chef, and for his first seasonal menu overhaul, Eric Jorgensen's showing a lot of promise. Case in point: seared sea scallops come with acorn squash puree and candied pumpkin seeds; roasted pumpkin and sweet potato soup gets a dash of pimentón honey; and the clincher: Gala apples are folded into dessert empanadas and glazed with Licor 43 anglaise. 

2024 N. Halsted St.; 773-935-5000

Caldereta at Sunda
It's stew season, and few look more promising than Sunda's. The caldereta is a contemporary take on a traditional, hearty Filipino stew made with lamb riblette, foie-tomato gravy and Asian tapenade, whose briny qualities help temper the decadent meatiness of the dish. 

110 W. Illinois St.; 312-644-0500

Wild mushroom pierogi at Woven & Bound
There’s plenty to savor at Woven & Bound, the new American brasserie inside the  Marriott Marquis Chicago in the South Loop. Courtesy of executive chef Joshua Murray, the menu takes guests all over the globe and through the seasons, starting with plates like wild mushroom pierogi. Inspired by Chicago’s Polish population, these umami-packed dumplings double down on fall flavor with Brussels sprouts. 

2121 S. Prairie Ave.

Butternut squash pizza at Stella Barra
Stella Barra greets autumn head-on with a menu addition showcasing one of the season's signature flavors. The butternut squash pizza sports a balanced mashup of sweet, spicy and herbal notes with candied bacon, Taleggio cheese, Fresno chilis, green onion, parsley and oregano. 

1954 N. Halsted St.; 773-634-4101

Apple pastries at Bake
All year long, Bucktown’s adorable Bake rounds out its staple cupcakes, brownies and cookies with seasonal treats. That means apples are now filling up the pastry cases. Try the flaky and buttery apple hand pies for a dose of Americana nostalgia, or opt for an almond-apple tart for something on the creamier side. There’s also caramel apple brioche bread, which blends sweet, tart and salty. 

2246 W. North Ave.; 773-384-7655

Baked halloumi at Ēma
In addition to the crowd-pleasing pumpkin hummus, which is back on the menu for the season, Ēma is working wonders with cheese for some menu additions. You’ve never tastes baked halloumi like this before, strewn with black plums, toasted almonds, honey, mint and aleppo. 

74 W. Illinois St.; 312-527-5586

Steak at Nacional 27
Chicago’s original Latin restaurant has added a new steak-focused menu, with preparations from various Latin countries. Highlights include a Cuban skirt steak with lime-mojo, Peruvian skirt steak with aji-amarillo and Argentine crusted filet medallions with an herbaceous chimichurri. 

325 W. Huron St.; 312-664-2727

Chicken nuggets at Split-Rail
Humble chicken nuggets get an upgrade at Split-Rail, where chef Zoe Schor proves her penchant for elevated Americana with a menu that’s equal parts playful and contemporary. The nuggets are plump morsels freshly fried and served with a side of tangy honey mustard for dipping. 

2500 W. Chicago Ave.; 773-697-4413

Rollin’ Down Rodeo at Broken Shaker
The new menu at Broken Shaker is a big deal. For starters, the bar and kitchen are pouring effort into sustainability. Not only have they adopted more compostable straws and garnishes, but they’re reusing and repurposing extraneous ingredients and scraps. For example: the Rollin’ Down Rodeo cocktail, a potent rye whiskey and coffee cocktail that employs leftover grinds from Cafe Integral to infuse a housemade spiced coffee liqueur. It’s rounded out with Lot 40 Rye, Johnnie Walker Black Label and Amargo Ballet.

19 E. Ohio St.; 312-940-3699 

Veal breast and langoustine duo at Nico Osteria
Here’s a surf 'n' turf you don’t see often. A newcomer to Nico’s seasonal menu is a combo of crispy-skinned veal breast and plump langoustines served with lobster mushrooms, cabbage and roasted apples for a mashup of soothing, harmonious flavors that smack of Eastern Europe. 

1015 N. Rush St.; 312-994-7100

Horchata Cocktail at Revival Social Club
There’s a slew of seasonal drinks at Edgewater’s Revival Social Club, but the creamy Captain’s Orders is the most tempting. Featuring housemade horchata, El Dorado 8-year aged rum and Shipwreck spiced rum, this deceptively easy-to-drink libation packs a boozy punch, while rice water keep things sweet and smooth. 

1133 W. Granville Ave.; 773-293-6435

Tagliolini nero at The Kennison
There’s a new pasta power player in town, as evidenced by a stream of impressive al dente dishes rolling out of The Kennison’s kitchens. The latest: a jet-black tangle of tagliolini nero swirled with crab, bottarga, chiles and basil for a balanced medley of salty, spicy and herbaceous. 

1800 N. Lincoln Ave.; 312-981-7070

Loaded donut holes at 1901 Restaurant at AceBounce
The game-changing restaurant at this subterranean ping-pong haunt isn’t messing around when it comes to sweets. On the brunch menu, guests can (and should) order a tray of donut holes flecked with maple and bacon and adorned with hot fudge. 

230 N. Clark St.; 773-219-0900

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