5 Reasons Chicago Should Be Your Next Getaway
If it's been a while since you hit the pavement in Chi Town—or if you've never been at all—now's the time to get reacquainted. With white-hot restaurants, swanky boutique hotels, and hip neighborhoods galore, here's why the Midwestern gem is a shoo-in for your next domestic trip.
A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.
1. Sleek hotels
From hip indie outposts to refurbished grand dames (and everything in between), Chicago’s hotels nail Midwestern hospitality. In the River North neighborhood, not far from the Magnificent Mile, one of our favorites—the revamped Eurostars Magnificent Mile—makes a persuasive play for Windy City visitors with sleek, urban-inspired rooms. But concrete ceilings, hand-scraped hardwood floors, private balconies, and spa showers are just a fraction of the hotel’s draw.
At Portsmith, the hotel’s elegant seafood joint, an elevated menu from executive chef Nate Henssler meets stylish nautical design (think: lots of navy blue, brass pendant lighting, and pearly floor tiles). Taking a “less is more approach” to dishes, the restaurant pays special attention to raw and lightly cooked plates like tuna tartare (with umami shrub, cilantro, and market chilies) and fancy oysters (with kombucha mignonette).
Just upstairs, at Leviathan—a sea monster-inspired bar—Benjamin Schiller whips up exotic cocktails in custom-made pewter mugs and smokey terrariums. Though the level of presentation is quite impressive, the specialty drinks really wow with unexpected ingredients and garnishes like blue thistle and shaved bonito flake. Our pick of the whimsical list goes to the Kraken, with Blackstrap rum, Hamilton 151, Smith & Cross, lime, grapefruit, honey, cinnamon, star anise, and squid ink tuile.
On the 26th floor—AKA the rooftop—the posh Apogee lounge draws both guests and walk-in locals with arresting city views and an expansive drink list including large-format cocktails like the Mr. Nice Guy (Absolut Elyx vodka, ginger, pineapple, and white oak and lemon smoke). When it’s chilly, cozy up to one of the outdoor, state-of-the-art glass fireplaces, or simply step inside and enjoy the elegant interiors; we’re talking marble-topped tables and bar, brass lighting fixtures, and deep-blue mohair sofas.
2. Michelin-starred kitchens
Chicago’s culinary scene is on fire. With celebrity chefs, diverse restaurants, and a slew of iconic Midwestern institutions (see: Portillo’s, Lou Malnati’s, and Giordano’s) on every corner, visitors aren’t hurting for a good meal. The city also isn’t a stranger to Michelin-starred kitchens—the 2020 roster includes 25 restaurants.
If your budget has room for one splurge-worthy meal, make a res at Smyth, which received two stars in the 2020 guide. The bi-level New American kitchen takes queues from rural Smyth County, Virginia, where executive chefs John and Karen Urie Shields worked with local growers. For a more casual meal, you can opt to be seated downstairs (in The Loyalist dining room—technically a second venue), but if you’re about the tasting menus (5-, 8-, and 12-course), you’ll head upstairs. Come hungry in order to clean up plates of aged lamb with young peanuts and brioche doughnut with marmite butter.
3. Buzzy bars
From clubby cocktail dens to low-key beer halls and romantic wine bars to see-and-be-seen rooftop lounges, Chicago is awash in all manner of watering hole. That said, West Town’s Beatnik—a globally-inspired restaurant and lounge—is our current space of choice.
The menu features a variety of Eastern Mediterranean, Asian, and Latin flavors, while cocktails from beverage director Jesse Filkins are sustainable and innovative. Options among the shaken, stirred, and slushie categories include Barefoot in the Park (vodka, fino sherry, melon, mint, lemon, guajillo spice) and The Sidehacker (Spanish brandy, amaro, lemon, gomme dem, Angostura & orange bitters).
Between eating and imbibing, you’ll be entranced by the décor. The Bonhomme Hospitality Group kitted out the former clothing store with pieces from Bali, Italy, Egypt, and more, combining arresting crystal chandeliers, Persian area rugs, and lush palms. Fall and winter visitors will also find the Andalusian-style, year-round courtyard particularly comfortable.
4. Hip neighborhoods
If you’re a fan of Brooklyn’s Williamsburg or London’s Shoreditch, then we have another neighborhood for you: Chicago’s Wicker Park. The once residential hood—just south of Bucktown and west of Humboldt Park—has transformed into a hipster haven rich in vintage shops, European-style cafés, and up-and-coming designer boutiques. Hunt down eclectic pieces and small-batch apothecary goods (from brands like Good & Well Supply Co. and Ursa Major) at Una Mae’s, and ‘80s and ‘90s fashions and housewares at Kokorokoko.
Before you hop the L train en-route to your next neighborhood of the day, make a pitstop for snacks. Big Star curbs taco cravings with an authentic Mexican street food menu; Stan’s Donuts has more than 50 varieties to please your sweet tooth (we’re all for the lemon pistachio old fashioned); and Mindy’s Hot Chocolate kills the dessert game with seasonal sweets (like the milk chocolate cream pie with whipped hot chocolate, chocolate tahini rice crispy, and coffee cocoa nib anglaise).
RELATED: The Best Boutique Hotels in Chicago
5. Can’t-miss seasonal events
Innovative architecture is at a premium in Chicago—just look to the city’s contemporary skyscrapers, historic Polish cathedrals, and residential greystones. To get a better feel for it all, visitors can check out events linked to the 2019 Chicago Architecture Biennial, September 19 through January 5. With anchor exhibitions spread throughout seven museums and institutions (think: DePaul Art Museum and Hyde Park Art Center), as well as installations and series at a number of smaller venues city-wide, there are a handful of events on offer every day.
If you’re in a shopping mood, you can hit the Randolph Street Market Festival just as it kicks off indoor season (end of October through April) in Chicago’s Beaux Arts-style Plumbers Hall. With more than 125 vendors hawking vintage fashions, city ephemera, repurposed furnishings, and all sorts of snacks stands, there’s truly something for everyone.
- The 10 Best Places to Travel This October
- The Most Underrated Cities in America
- 15 Incredibly Cool Suede Jackets We’d Love to Slip Into
All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.