7 Must-Book Restaurants in Chicago for Your Fall Bucket List

The Dearborn's Midwestern fried chicken | Credit: Neil Burger

As the seasons change, so do the restaurants. Chi-Town is known for its food scene, and there’s a reason reservations are flying off the shelves as dining out returns. Restaurants are getting inventive with new chefs, menus, and spaces. Tables are going fast as the all-star teams of television chefs, MICHELIN-lauded chefs, and veteran Chicago chefs showcase their skills. There’s a time and place for everything on this list, from Italian to American to Latin street food. Here are the seven must-book places in Chicago right now. 

Rose Mary (West Loop) 

Pork ribs pampanella

Credit: Matt Haas

Famed chef Joe Flamm, well-known for winning Top Chef season 15, opened the doors to this Italian-Croatian West Loop restaurant that has been repeatedly booking out tables two months in advance since opening in March. Named after his grandmothers, Mary and Mary Rose, and the herb rosemary native to Italian and Croatia coasts, Rose Mary brings together Flamm and his wife Hilary Delich’s heritage, respectively. Flamm coins the vibrant seasonal menu as “Adriatic drinking food” — think coal-roasted beets with kajmak, pistachio, and honey; squid ink risotto with lobster brodo and confit squid; and pork ribs pampanella with agrodolce sauce. Fill your glasses with a “golden negroni” or a white rum “plum’s the word” cocktail for the full experience in the warm-toned, tiled restaurant that evokes a Croatian konoba-esque interior (a tavern in the Dalmatian region).

Adalina (Gold Coast)

Adalina

Credit: Matthew Reeves Photography

From the executive chef who earned the first MICHELIN star for a brewpub comes this timeless Italian restaurant in the Gold Coast neighborhood. Fusing together Northern and Southern Italian fare, chef Soo Ahn brings to the table steak tagliata with Parmigiano Reggiano and artisanal handmade pasta such as lumache with lobster and crab. Ahn puts his own take on the Chicago Italian-American specialty chicken vesuvio (roast chicken and potatoes in white wine) in salmon vesuvio with potato gnocchi. Plus, don’t miss the quattro formaggi (four cheese) garlic-stuffed bread. Since Adalina opened in June in the former Walton Street Kitchen & Bar two-story space, it has already earned a well-deserved spot as a must-book destination.

Dusek’s Tavern (Pilsen)

Dusek's Tavern

Credit: Sandy Noto

Take a pub, dress it up with chic antiques, pop it next to a landmark music venue like Thalia Hall, and add a top chef like Ben Truesdell (formerly of Pacific Standard Time and The Publican) to the mix — and you’ve got Dusek’s Tavern, formally Dusek’s Board & Beer. The remodeled Dusek’s reopened in May after a seven-month-long closure with Truesdell as executive chef and ​​Ashley Robison as pastry chef, plus a new mix of contemporary American dishes alongside natural wine. Start with the hot butterflake rolls, followed by dishes from the wood-fired hearth such as pork chop and Mt. Lassen trout. Dessert comes in the form of a divine blueberries and peaches summer galette. Pro tip: Every Thursday at this updated neighborhood favorite, snatch up $2 oysters and half-off Champagne during happy hour. 

Bandit (West Loop)

Bandit Chicago

Credit: Mark Ballogg

Upscale dive bar Bandit took it to the next level quite literally this July, expanding to a second floor for the two-year-old bar. The new 4,000-square-foot floor holds 150 people and restaurant group DineAmic did not hold back on the decor — going all out with dollar sign wallpaper and a gold sequin wall with the word “BANDIT” in all caps plastered across it in red sequins, serving as the backdrop to a live DJ at night. Similar to the first floor, the bathrooms are decorated with iconic superstars such as Elton John, Destiny’s Child, and the Spice Girls. As for the food, bar bites include bulgogi short rib waffle fries with kimchi and mozzarella sticks with parmesan ranch and marinara sauce, and entrées run from salads and sandwiches to tacos and steak fajitas. Bottomless weekend brunch is a crowd favorite with two hours worth of mimosas, bloody marys, and bloody marias. Bonus: You can bring your pup to this dog-friendly restaurant.

Pilsen Yards (Pilsen)

Mezcal Margarita

Credit: Sammy Faze Photography

Jam out to vinyl DJ sets with a taco in one hand and margarita in the other at Pilsen Yard’s new-ish outdoor patio, open since January. Chef Carlos Cruz whips up Latin street food such as sweet corn tamales, al pastor tacos, and drunken rum tres leches, and the mezcal and tequila selection might make you lost for choice, but you can never really go wrong with a house margarita. The exposed brick and wood beam ceiling give off warehouse vibes, with heated floors and overhead heaters to brave the Chicago winters. Pilsen Yards also hosts weekly happy hour deals and a monthly neighborhood discount.

The Dearborn (The Loop) 

The Dearborn

Credit: Sean Henderson

This refined American tavern sits in the heart of the Loop, steps away from Millennium Park. The restaurant, opened in 2016 by Irish sisters Amy and Clodagh Lawless, serves up Midwestern-focused cooking in stylish digs of chandeliers and plush red sofas. The versatile menu covers all the bases with pizzas, burgers, fish and chips, Midwestern fried chicken, mezes, and Dutch apple pancakes, making it work for all occasions, from a pre-theater bite to post-work cocktails and business lunches. As crowds slowly return to Chicago’s Loop, expect The Dearborn to be seeing a lot more action, too. 

Chicago Cut Steakhouse (River North)

Steak

Credit: Stephen Hamilton

A power meal destination if there ever was one, Chicago Cut Steakhouse has hosted countless A-listers since its opening in 2010, such as Oprah Winfrey, Kate Upton, and Ryan Seacrest, to name a few. Since its reopening in April, after a four-month-long pandemic closure, eager diners have flocked to get a taste again of the beloved 35-day dry-aged steaks with sides of truffled scalloped potatoes, creamed spinach, and green beans almondine. The luxurious red leather seats are well suited for its lavish dishes, such as the “lobsterscargot” — Maine lobster tail in garlic butter baked with havarti cheese and served with crostinis. It’s a treat-yourself kind of meal, complete with riverfront city views.

Tried them all? Check out other options here.