As summer winds down, Chicago’s culinary scene revs up, with an abundance of dining experiences that are perfect for the season — from al fresco brunching in the city’s last warm days to hunkering down in cozy old-school stalwarts. So whether you’re planning to dine out with pals, enjoy an intimate date night by the fire, or treating yourself to a solo snack at the bar, here’s a look at all the meals we can’t wait for this fall.
1. Take advantage of outdoor dining while it lasts.
From intimate date night dinners to spreading out with a group on the weekends, there are still plenty of outdoor options this season. Park and Field’s sprawling patio is the spot to sip ciders and nosh on buffalo chicken nuggets and barbacoa nachos. After a game of bocce ball, cozy up by one of their two firepits. For a quieter patio experience, Bistro Campagne offers a pleasant first-come, first-served outdoor seating section reminiscent of a French villa. You’re here for classics like steak frites and escargot and a selection of French wines.
2. Raise a glass to autumn.
Pompette’s warm globe pendant lights and airy ambiance might entice you to linger from morning to night. The all-day café and wine bar serves coffee and pastries in the morning, moves to a stellar happy hour in the afternoon, and then rolls into dinner service with an Italian- and French-inspired menu of shareable plates like burrata tartine, crab croquettes, and mushroom-and-herb agnolotti pasta. Delivering epic views and rooftop fire pits, Cindy’s Rooftop is your destination for seasonal cocktails to toast to the changing leaves.
3. Try a new hotspot.
From the folks that brought us Indienne, Sifr in River North offers a contemporary twist on Middle Eastern cuisine, boasting plates like chicken liver pâté and grilled vegetables and meat kabobs. Other newcomers include Evanston’s Zentli, where Mexican street food can be enjoyed within an art-adorned setting, and chef Otto Phan’s latest venture, Kyoten Next Door, a more affordable but still mind-blowing omakase experience in Logan Square.
4. Bring everyone together with a group dinner.
Looking for a great group spot? Bucktown’s trendy cocktail bar and restaurant Chef’s Special serves a Chinese American menu that skillfully fuses the classics with the new. Don’t skip their Thai chili-smothered crispy chicken, which pairs nicely with a cocktail heaped with fresh botanical ingredients. Meanwhile, chef Zach Engel has crafted an exceptional seasonal Middle Eastern menu at Galit — don’t miss the smoked turkey shawarma, falafel, and all of the mezzes. And at Monteverde, nearly all of the housemade pastas are meant to be shared, though we do recommend ordering an extra cacio whey pepe for the table.
5. Go on an outdoorsy outing, then reward yourself.
The best way to end a day of exploration is to treat yourself to dinner. Kayak down the Chicago River with Wateriders and then refuel nearby at Ciccio Mio, over a bowl of spicy vodka rigatoni or ricotta gnocchi. Or take a stroll along the lakefront or Northerly Island and then head to Apolonia, Stephen Gillanders’ European-Mediterranean restaurant, which serves a small but mighty menu of grilled meats and raw seafood. Start with an order of the black truffle puff bread and a cocktail, and go where the mood takes you from there.
6. When it gets chilly, indulge in some comfort food.
Chilly afternoons and early sunsets mean it’s finally time to sink into those hearty burgers and pastas we so crave. At The Village Restaurant, it isn’t just the white tablecloths, nostalgic décor, and framed photos of celebrities lining the wall that make it a classic stalwart — it’s the indescribable sense of warmth. Take your time, order some wine, and save room for a post-pasta brandy and tiramisu. Union in Logan Square is your go-to for elevated American pub grub (think brisket burgers with bone marrow aioli) and a pint, with some two dozen-plus rotating draft beers.
7. Treat yourself to a fall dessert.
There’s nothing like the temperature drop to awaken that sweet tooth. Cozy up in a leather booth near the fireplace inside Armitage Alehouse and order from their dessert menu, which includes sticky date cake and root beer floats. And apart from beer, Moody Tongue Brewery’s ten-layer German chocolate cake is a no-brainer, as is Gilt Bar’s happy hour, which includes a “teeny martini” that pairs nicely with their gooey skillet cookie with vanilla ice cream.
8. Cozy up to a good book at these spots that are perfect for solo dining.
Before all the holiday festivities begin, enjoy some solo time at Scofflaw, a cozy gin joint with a crackling fireplace. Over at Trivoli Tavern, you’ll find that oysters, coal-fired seafood, and a stiff drink are perfect companions for a solo night out, all within a low-lit and captivating old-world setting.
9. Embrace the season’s produce at a farm-to-table restaurant.
Now that fall is here, new ingredients are making their way to seasonal vegetable-forward plates across the city. Logan Square’s Lula Café has long been Chicago’s farm-to-table all-star and gets everything right, from an unbeatable ambiance to high-quality local and seasonal ingredients. Keep an eye out for the green harissa chickpea and fennel tagine.
10. And now that everyone’s back from vacation, it’s time to rally the crew for brunch.
The Duck Inn, as the name suggests, is the place to enjoy all things duck-related, plus an impressive lineup of cocktails by Brandon Phillips. Try the “Egg McDuckinn:” a fried egg and sausage patty sandwich with griddled onions, stacked inside an English muffin and spread with maple black pepper mayo. Their famous duck dog, with Chicago-style toppings (yes, relish) is also available for brunch.