Best Restaurants for Fall in Chicago

Get cozy at Chicago's best restaurants for Fall dining and drinking

It's time to reject charcoal lemonade and poké bowls and order anything soaked in smoky whiskey or sticky maple. If a German  experience lifts your spirits, The Publican's annual Oktoberfest celebration is your ticket to ride into autumn. In West Town, Funkenhausen's Funktoberfest celebration adds a wunderbar dash of autumn glee. One of the few restaurants left in the city that serves traditional German food, Himmel's gets even better with its autumn Oktoberfest celebration. Since you're replacing the fashion item of summer, midriff tops, for sweaters and jeans, splurge on hearty yet refined European fare at Lincoln Square's Cobblestone Restaurant & Cider Bar. It has been a difficult year and a half - so have a some Old World spaetzle  and a latke Benedict already. 

Executive Chef  at The Dearborn Tavern, Aaron J. Cuschieri, is expert at working the bounty of seasonal Midwestern ingredients into an attractive and most delicious autumn plate. Nonnina's lovely outdoor dining options warmed up for fall plus housemade pizza and pasta make it an appealing seasonal choice in River North.

Autumn heralds "The Coasts that Make Kostali," a monthly series of prix fixe menus throughout fall and winter, exploring the cuisines and culture of the coasts of Spain, Croatia, Israel and Morocco. When the weather cools, head south, as in the South Loop's Sociale. They ignite the fire tables on the expansive patio and inside, the restaurant's wood-burning oven serves as seasonal aromatherapy. Boka Restaurant Group's brand new Alla Vita ("to life") brings a casual, family-style menu of comforting Italian cuisine to the West Loop that should make both nonni and food snobs swoon.




So you couldn't take that trip to Italy last year. Or this year. You won't mistake Clark St. for Rome's Via del Corso, but Nonnina's sweet River North sidewalk patio, the open-air tent Casa Nonnina, and the al fresco off-street patio under twinkly Tivoli lights feel awfully like a casual neighborhood trattoria serving authentic Italian food and wine. Just like the neighborhood trattorias of Italy, the Chicago restaurant serves classics made with locally sourced, seasonal ingredients. Nibbling housemade pasta and pizza, entrees and frilly salads in the garden atrium or on the fresh-air, heated patio is transportive. Start with a cheese board, sausage and peppers or fritto misto of shrimp, squid, bay scallops and batons of zucchini. Earthy fall salads include roasted red and golden beets and breaded eggplant accompanied by local mozzarella and roasted cherry tomatoes. Share a leek and mushroom pizza with bubbly edges or any of 10 handmade pasta dishes. There's a seasonal fish of the day, old-timey Chicken Vesuvio or Chicken Parm, or lovely grilled veg. Have fun pronouncing "Tortino di Ciocccolato" while waiting for the flourless lava cake with raspberry accoutrement to appear.

Recommended for Best Restaurants for Fall because: Nonnina's various outdoor dining options warmed up for fall plus housemade pizza and pasta make it an appealing seasonal choice in River North.

Jacky's expert tip: Stop by for Happy Hour at the bar, Mon.-Fri., for $6 pours of house wine; $7 cocktails and tempting bites like a half-dozen oysters for $10.

Read more about Nonnina →

Just the name, Cobblestone Restaurant & Cider Bar, sounds like a portal into autumn and the Lincoln Square eatery's European fare, cozy courtyard and lengthy scroll of hard ciders and craft beers affirm fall as the most comfortable of seasons. Executive Chef Michael McCloud fills the menu with hearty and shareable items like cider braised pork belly with crisped skin, smoked pink lady apple sauce and rye maple glaze; seared Porcini spaetzle with foraged mushrooms and heirloom cider Jaeger; pan-roasted chicken; and braised short rib with Sunday gravy and whipped celery root. Moisten the pipes with selections from the extensive cider list, European and local craft beers and European specialty cocktails. Traditional coffee service, skillet apple crisp or a warm butterscotch fudge bar make a fine conclusion. Indoors the space is adorned with antique ceiling fans and a long wooden bar punctuated with leather stools. The sidewalk café is open year-round with a retractable canopy and warmers when the air chills and the courtyard boasts new murals.

Recommended for Best Restaurants for Fall because: Cobblestone's European fare, cozy courtyard, year-round patio and list of hard ciders and craft beers is the model of an autumn dining experience.

Jacky's expert tip: Weekend brunch is all about European comfort food, too: schnitzel & waffles, Dutch Babies and latke Benedicts.

Read more about Cobblestone Restaurant & Cider Bar →

Boka Restaurant Group, in partnership with chef Lee Wolen, just opened Alla Vita, an Italian-American restaurant showcasing fresh food made with the best ingredients. There's a spacious outdoor patio and Indoors, the space is adorned in Italian floral prints and Fornasetti inspired artwork, affording a casual, garden atmosphere that's especially inviting in the cooler months. Alla Vita's menu covers antipasta (wood-fired bread, tender orbs of arancini); salads; homemade pastas like cacio e pepe ricotta dumplings; pizzas, al forno such as lasagna with wild mushrooms and Fontina or whole Sea Bream; and vegetables. Wolen, a Michelin starred chef known for his chicken dishes at Boka and GG's Chicken Shop, presents a signature chicken dish at Alla Vita: one of America's favorite Italian comfort foods - Chicken Parmesan dinner for two or four guests. Alla Vita's wine program focuses on small, lesser known wineries and offers an extensive wine-by-the-glass option.

Recommended for Best Restaurants for Fall because: The new restaurant offers a casual, family-style menu of comforting Italian cuisine that should make both nonni and food snobs swoon.

Jacky's expert tip: Boka Restaurant's pastry chef, Kim Mok, takes the lead on sweets. Do not pass on classic Italian desserts like Tiramisu, Dark Chocolate Budino, and an assortment of gelatos.

Read more about Alla Vita →

West Town

Just the name, Funkenhausen, connotes, well - fun. But the West Town restaurant is no Disneyesque gimmick. The space is an elegantly casual beer hall and Executive Chef Mark Steuer mixes a magical Southern American/German culinary alchemy in the kitchen inspired by his Charleston roots and German family heritage. Enjoy colossal garlicky pretzels, bratwurst and smoked Amish chicken year-round but autumn brings a Funktoberfest celebration filled with special food, music and beer. Sept. 18 - Oct. 3, the West Town spot pours Oktoberfest beer in novelty mugs, apparel, and an Uber Piggy Plate starring smoked pork chop, haus bratwurst, pork belly, sauerkraut, pretzel, mustard, and pickles. Ach du meine Güte! Count on live music from the Oompa Band and surprise pop-up acts throughout the length of the festival. Order some fall beers including Pfungstädter Festbier, Maisel's Amber Hefeweizen, and Hirter Morchl Munich dunkel. Save space for freshly made pastries, too.

Recommended for Best Restaurants for Fall because: Funkenhausen successfully mixes a menu German and Southern inspired cuisine and its Funktoberfest celebration adds a wunderbar dash of autumn glee.

Jacky's expert tip: You're steps away from Alcala's Western Wear which makes a fun stop to search for authentic Western boots, buckles and spurs.

Read more about Funkenhausen →

Kostali by Naha, on the fifth-floor lobby of The Gwen Hotel, is helmed by James Beard Award-winning chef Carrie Nahabedian. The stylish, understated restaurant threads a maritime mosaic through the Mediterranean - think Spain, Italy, France, Greece, Lebanon and Morocco. It's great any time of the year, but autumn heralds a monthly series presented by the women of Kostali. Beginning in September and evolving monthly throughout fall and winter, the prix-fixe menus explore the cuisines and culture of enigmatic coasts including Sardegna, Italy, Dalmatia-Zadar, Croatia, Tanger-Tetouan, Morocco, Galilee, Israel and Cyprus. Dishes from Michelin Star Chef Carrie Nahabedian and Pastry Chef Danielle Marelli are escorted by beverage pairings that highlight female distillers and winemakers from each region. September's menu travels to Galicia, Spain via Spanish octopus, roasted shishito peppers, Prime rib eye, scallops or mussels plus a winning conclusion of Giandua Budino - a rich pudding similar to French pot de creme - this one with hazelnut, banana and dark chocolate. Can't do the prix fixe special? There's still Parisian gnocchi, incredible hummus with spiced lamb and do not overlook broccoli and cauliflower fritto misto with capers, chickpeas, chermoula and Pecorino.

Recommended for Best Restaurants for Fall because: The monthly menu series presented by the women of Kostali, will make you actually look forward to fall and winter in Chicago.

Jacky's expert tip: Drink up! The wine roster features Mediterranean coastal regions and cocktails incorporate regional spirits and mixers like Aegean tonic, Italy's limoncello and figenzia vodka made with Grecian and Turkish figs.

Read more about Kostali →

Fulton Market

The Publican's annual Oktoberfest celebration attracts clamorous crowds to the expansive dining hall and outdoor patio for feasts full of pretzels, sausages and beer. While the party has been a weekend-long event in the past, the Fulton Market restaurant expands this year's event into a two-week long festival celebrating the Bavarian tradition. From Sept.17th - Oct. 3rd, there's a daily Oktoberfest menu featuring six family style courses of traditional fare. On Sunday, Sept. 19th and Sunday, Oct.3rd, The Publican is hosting a ticketed Oktoberfest party where revelers are treated to eight courses of German-inspired favorites, served family style. Pull on the lederhosen and dirndls to immerse yourself in the experience and get ready for live polka music. Even if you miss these events, The Publican's hearty menu, extensive international beer roster and beer hall space evoke fall in the most delicious way.

Recommended for Best Restaurants for Fall because: You can entertain your inner Arnold and party Oktoberfest-style at The Publican's Teutonic fall fête.

Jacky's expert tip: The Publican is akin to a European beer hall, so expect an exuberant, spirited dining experience.

Read more about The Publican →

Lake View

Get out of River North and Fulton Market for crying out loud and spend a fall evening at Wood, an upscale casual neighborhood spot in the heart of Chicago's Northalsted. It's Chef Devin Kreller's bully pulpit of classic French cookery combined with the best seasonal produce from family farms. There are house-butchered meats from Illinois, house-made charcuterie, and the intoxicating scent of just-baked bread exiting the wood-fired oven. Slip into a salmon-colored banquette or a seat at the wrap-around bar and nibble pork lardo toast - a savory wonder. Chef's autumn menu includes wood grilled quail with balsamic, rosemary, charred radicchio and roasted local farm grapes; braised chuck beef rib "pot au feu" with soy braised turnip, ginger and shio kombu; and sage butter roasted heritage chicken breast accompanied by Boudin blanc sausage, cranberry beans, leek veloute and local wild rice. If your cheeks aren't rosy from a chill in the air, they certainly will be after you try fall drinks like a sweet potato sour as well as hot cocktails.

Recommended for Best Restaurants for Fall because: Wood, a six-time Michelin Bib Gourmand winner, is a wonderful neighborhood restaurant offering soulful seasonal food and drinks.

Jacky's expert tip: Wood is just a few blocks from Briar Street Theater if you're heading to a Blue Man Group show.

Read more about Wood →

When the weather cools down, head south. The South Loop's Sociale lights up the fire tables on the expansive patio and inside, the restaurant's wood-burning oven serves as seasonal aromatherapy. Order a warm handmade cocktail and get your appetite ready for wood-roasted chicken; sumac dusted Diver Sea Scallops with pistachio butter emulsion and micro arugula (this may be the best scallop dish on the planet); and wild boar & lamb meatballs with sweet soy/teriyaki tomato sauce and prosciutto togarashi migas. Yeah, that's a lot of words but, trust us, chef/owner Martin Murch is a magician with fancy or simple autumn ingredients like apples and squash. Make a fine meal out of a stellar array of appetizers like polenta Parmesan fries with miso wasabi and Sriracha aioli dipping sauces; wild mushroom flatbread; crispy potato gratin; and grilled eggplant with Feta, roasted red peppers, charred red onion, yogurt dill sauce and balsamic. The famished will not be disappointed with Sociale's smoked Prime Rib dip, colossal burger, steaks or salmon. Finish with bourbon semi freddo or little doughnuts and it's almost time for bed.

Recommended for Best Restaurants for Fall because: Sociale's wood burning oven, outdoor fire tables and robust modern menu of skillfully prepared dishes make it a must visit this fall.

Jacky's expert tip: Sociale is a popular choice for weekend brunch, too, as the kitchen turns out hearty plates like the Printers Row Breakfast; Sociale Benedicts with Wagyu steak or Maryland Crab Cake; and various skillets, omelettes and pancakes.

Read more about Sociale →

Irish owned but utterly American, The Dearborn can be found at the intersection the Theater District, satisfying food and lively ambiance. Executive Chef Aaron J. Cuschieri is expert at working the bounty of seasonal Midwestern ingredients into an attractive and most delicious plate. Whatever you order, launch with buttery, warm Everything Parker House rolls served with Boursin-cream cheese spread and soon your eyes will roll up into your head. Chef's exceptional autumn dishes include Rohan Duck Breast: duck rillettes 'cigar,' charred radicchio, roasted Castelvetrano olives, black mission figs, frisée, goat cheese, honey-lavender glaze and Kabocha squash soup. How about Pork Three Ways when it's soy-braised pork belly, roasted pork loin and confit pork cheeks with a warm salad of sugar snap peas, Bosc pears and Delicata squash, wilted spinach, Sunchoke mousse, garlic chips, apple cigar gastrique and natural jus. Menu items are earthy yet elegantly presented. Open for lunch, brunch and dinner, The Dearborn is also a smart stop for classic and creative cocktails and apps pre-or-post theater, museum browsing and shopping in the Loop.

Recommended for Best Restaurants for Fall because: The Dearborn may be one of the best places to dine and drink in The Loop and autumn brings an additional bounty of comforting, seasonal dishes.

Jacky's expert tip: Don't miss Pastry Chef Julianna Westgor's chocolate and peanut butter tart or caramelized white chocolate carrot cake which are simultaneously nostalgic and modern.

Read more about The Dearborn Tavern →

When you want an injection of "die Fröhlichkeit" know that it's Oktoberfest all year long at Himmel's. Upon entry, the decor and scents transport you to Munich, hometown of owners Carol and Dianne Himmel. Count on a number of from-scratch German dishes this fall including: Bavarian pork shank prepared Munich style, crispy outside and tender and juicy on the inside, served with mushroom gravy, pretzel dumplings and cabbage salad; sauerbraten; wurst platter; wiener schnitzel; and comforting liver dumpling soup among the options. Those are in addition to tempting year-round menu items such as homemade spätzle baked with Swiss and Gruyere, wild mushroom stew and family recipe strudels. Pair it with several German beers on tap. Bring along little Harold and Heidi for kids' dishes like schnitzel with mashed spuds or even spaghetti with a meatball. Visit Friday to Sunday, Oct. 8-10, for rousing live German Music by the Phenix.

Recommended for Best Restaurants for Fall because: One of the few restaurants left in the city that serves traditional German food, Himmel's gets even better with its autumn Oktoberfest celebration.

Jacky's expert tip: Don't feel like sauerbraten? Formerly Pizza D.O.C., Himmel's kept the pizza oven and D.O.C. standards so you can also experience a wúnderbar pie.

Read more about Himmel's →


Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky