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Cindy’s Rooftop

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How to Eat Your Way Through Chicago in One Day

Make every second count

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As the Midwest's unofficial capitol, Chicago welcomes millions of visitors each year. Thanks to the city's impressive culinary depth, there are countless options to satisfy hunger. It would take weeks of nonstop eating just to scratch the surface of everything available so for those with limited time, picking just a few restaurants might seem like an overwhelming task. To make things less daunting, the 24-hour itinerary below will help both visitors and locals alike by highlighting some of the most essential spots in town.

8 a.m. — Doughnut Vault

Doughnut Vault/Facebook

Exploring the city on an empty stomach is a perilous adventure so start the day off right with a sugar-fueled rush courtesy of Doughnut Vault. The shop is just one of many projects from restaurateur Brendan Sodikoff and his company Hogsalt Hospitality. Sorry Dunkin’ but Chicago runs on these perfect buttermilk old fashoneds, pillowy glazed doughnuts, and other assortment of classic flavors. It’s high praise, too, considering the number of doughnut purveyors around town. Still not convinced? Check out the lines that form before opening. Get there early because once the offerings are gone, they’re gone. Seasoned fans know to follow Twitter for the day’s specials and availability. The original store, located at 401 N. Franklin Street, opens at 8 a.m. on Mondays through Fridays and 9:30 a.m. on weekends. A second location is at 111 N. Canal Street.

9 a.m. — Manny’s Cafeteria & Delicatessen

Tim McCoy/Yelp

Old-school Jewish delis are a dying breed but as long as the city has Manny’s, there’s no reason to panic just yet. The South Side institution has been in business since 1942 and although the space was remodeled two years ago, little else has changed. Generous portions of corned beef hash, a breakfast Reuben sandwich, and other diner favorites ensure that folks leave full and satisfied after the most important meal of the day. Cafeteria-style service also keeps things moving along quickly – a huge benefit when short on time. Need some food for later? Grab bagels or meats and cheeses by the pound from the deli counter.

12 p.m. — Chicago Athletic Association

Cindy’s Rooftop

The Loop certainly has a fair amount of sights and attractions vying for attention. One of the most popular is the Chicago Athletic Association thanks to its wealth of choices. The historic hotel, first opened in 1893, was revived in 2015 after the building underwent a complete renovation. Along with a facelift, the project added several new food and beverage spots. Beloved burger chain Shake Shack anchors the ground floor while Cindy’s, a tourist-friendly beach-house-inspired rooftop restaurant and bar, sits 13 stories high. Elsewhere, guests can spend an afternoon at Game Room playing billiards, bocce, shuffleboard, and other activities or travel back in time via Cherry Circle Room’s vintage space and refined takes on classic dishes. And for a pre-dinner drink, acclaimed mixologist Paul McGee uses rare spirits to craft unique cocktails inside a small eight-seat bar dubbed Milk Room.

3 p.m. — Xoco


Rick Bayless’s name is synonymous with Mexican cuisine not only in Chicago, but around the country. His Frontera empire continues to expand and explore new regions, flavors, and techniques. At casual sandwich shop Xoco, visitors can get an afternoon pick-me-up in the form of sweet treats. Golden fried churros are available in different glazes, or served with chocolate dipping sauce, while hot chocolates are made fresh from cacao beans that have been roasted and grinded in-house. If an extra boost is needed, coffee can be added to the drinks as well.

6 p.m. — Maple & Ash

Maple & Ash/Facebook

The breadth of the city’s culinary scene is remarkable. From mom-and-pop taquerias to world-class fine dining, restaurants are leaving no stone unturned in pursuit of the next great bite. At its core, though, Chicago’s reputation as a meat-and-potatoes kind of town cannot be denied. Steakhouses are seemingly on every block downtown and more are opening up regularly. Among those ushering in a new beef experience is this posh Gold Coast spot. Yes, the chic design — complete with high ceilings and ornate chandeliers — is in line with expectations but the boisterous dining room lacks any hint of pretension and fosters a relaxed atmosphere. Guests start things off with a complimentary cocktail before delving into the luxurious menu. Executive chef Danny Grant, who previously earned two Michelin stars at Ria, utilizes a 12-foot hearth to cook items like 28-day dry-aged rib eye and fire-roasted seafood towers, a fresh twist on a chilled steakhouse staple. Big spenders or expense accounts should put their trust in Grant and go with the aptly-titled “I Don’t Give a F*@k” menu for a tasting of his greatest hits.

9 p.m. — The Aviary

The Aviary/Facebook

There are lots of watering holes in Chicago but this stunning, award-winning cocktail temple has no equal. It’s the brainchild of Grant Achatz and Nick Kokonas, a pair who have put Chicago on the map as a global dining destination with innovative restaurants like Alinea and Next. Beverage director Micah Melton dazzles guests with theatrics and liquid alchemy that pushes boundaries. Whether it’s served in a porthole infuser or encased in an ice sphere, each concoction is rooted in science and guaranteed to be a one-of-a-kind experience. The fun doesn’t end there. Hidden below The Aviary is The Office, an intimate speakeasy specializing in classic drinks. Together, the two bars offer a yin and yang approach to mixology. Reservations for both can be booked on Kokonas’s proprietary ticketing system Tock.

11 p.m. — Kingston Mines

Kingston Mines/Facebook

Just like deep dish pizza and a Chicago-style hot dog, the blues are an integral part of the Windy City’s identity. And while music venues are aplenty, this Lincoln Park landmark is the oldest continuously-operating blues club in town. Founded in 1968 and open seven days a week, Kingston Mines supplies an almost endless amount of live entertainment. Two acts perform across two stages every night until as late as 4 a.m. so that the good times roll into the early morning. The kitchen is likewise open late and keeps the party going with Southern comforts such as po’ boy sandwiches and barbecue ribs. From start to finish, it’s a soulful experience that fully encapsulates the spirit of Chicago.

Manny's Coffee Shop & Deli

1141 South Jefferson Street, , IL 60607 (312) 939-2855 Visit Website

The Aviary

955 N. Morgan St & W. Fulton Market, Chicago, IL 60607 Visit Website

Kingston Mines

2548 North Halsted Street, , IL 60614 (773) 477-4646 Visit Website

Chicago Athletic Association

12 S Michigan Ave, Chicago, IL (312) 940-3552 Visit Website

The Doughnut Vault

401 1/2 N Franklin St, Chicago, IL 60654 (312) 464-9544 Visit Website


1471 N Milwaukee Ave, Chicago, IL 60622 (872) 829-3821 Visit Website

Maple & Ash

8 West Maple Street, , IL 60610 (312) 944-8888 Visit Website

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