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13 Chicago Airbnbs Worth Bookmarking, From Frank Lloyd Wright-Built Homes to Modern Lofts


13 Chicago Airbnbs Worth Bookmarking, From Frank Lloyd Wright-Built Homes to Modern Lofts

For solo trips, family vacations, and more.

If you’re interested in exploring the breadth and depth of Chicago’s renowned architecture, there’s a good chance you can start in your Airbnb. For a city that’s known the world over for its eclectic architectural collection of modernist meets gothic meets neoclassical, many examples of the Windy City’s historic cityscape lie outside the downtown corridor. From industrial lofts with soaring ceilings in the West Loop to a restored prairie-style home built by Frank Lloyd Wright to bright and airy condos in Oak Park, the Airbnbs below offer a taste of what makes this city so spectacular. Use them as your home base for some of the city’s best activities: an architecture boat tour along the Chicago river, meals and nights out enjoying its bustling food and bar scene, museums and walking tours through its inspired art scene, plus a trip to one of the must-visit beaches along Lake Michigan.

Courtesy Airbnb

Hip guest house in Humboldt Park

With a very unassuming entrance, you’ll be pleasantly surprised when you enter this airy studio in Humboldt Park. What it lacks in size it makes up for in design, with beautiful artwork, plenty of plants, and a renovated bathroom complete with a claw-foot soaking tub. The kitchenette features just the basics (a mini fridge, hot plate, tea kettle), so it’s best to take advantage of Humboldt Park and neighboring Wicker Park’s diverse food scene. Spend your days viewing local artists’ murals or paddling through the picturesque lagoon at the Humboldt Park boathouse.

Courtesy Airbnb

Sprawling penthouse in Old Town

If you want to explore one of Chicago’s trendiest neighborhoods in style, check out this 4,000-square-foot penthouse in Old Town. Just a few minutes from downtown, Old Town boasts incredible views of the cityscape, amazing restaurants, and the famous Second City comedy club. This apartment’s highlights include exposed brick walls and 120-year-old barn doors leading to a private rooftop deck overlooking the city. This is one of the best options for a big family or group of friends—inside, you’ll find four bedrooms, four full baths (including a hot tub with the primary room), two kitchens, and two laundry rooms.

Courtesy Airbnb

Restored Frank Lloyd Wright home in Rogers Park

Meticulously restored, the Emic Bach home—designed by famed architect Frank Lloyd Wright—is a steal at just over $500 a night (though prices may vary throughout the year). Located in Rogers Park, this home is next to Loyola University, steps from Lake Michigan, and walking distance to plenty of up-and-coming restaurants. The home itself is a work of art, with a beautiful built-in desk, a large living room, and outdoor patios off of each bedroom. The pièce de résistance is the second floor balcony, complete with a Japanese tea house, immaculately kept gardens, and ample outdoor seating. Built in 1915 for one of Wright’s admirers, this house is a must-visit for art and design lovers.

Courtesy Airbnb

Chic corner loft in Fulton Market

Located in one of the city’s best food neighborhoods, you’ll have no trouble finding great places to eat when you’re staying in this 1920’s corner three-bedroom loft in Fulton Market. With 15-foot ceilings, the large windows offer incredible views of the neighborhood, and the rest of the 2,500-square-foot loft features restored concrete floors and exposed brick and timber. You’d be remiss not to try some of the neighborhood’s best restaurants, including Girl & the GoatRoister, and Aba, or to explore the area’s local shops and galleries. Additionally, you’re just a quick Uber ride away from Magnificent Mile, the riverwalk, and Millennium Park.

Courtesy Airbnb

Private penthouse in Ukranian Village

You’d be hard pressed to find a better view of the city than this private penthouse in Ukrainian Village. Featuring a large patio on the roof and a smaller patio off the living room, there are plenty of ways to take in the skyline here. Inside the Chicago Airbnb there are rich leather furnishings and floor-to-ceiling windows sunning the space in natural light, a large kitchen, and two bedrooms and baths. This westside neighborhood is home to over 50,000 Ukrainian families—the second largest population in the country—so be sure to check out the area’s many tributes to their homeland, including the Ukrainian Institute of Modern Art, the Delta gift shop, and the TryZub Ukrainian Kitchen.

Courtesy Airbnb

Mid-century townhouse in Wrigleyville

Just steps from Wrigley Field, this three-bedroom home is the ultimate pad for baseball fans. Decorated with chic mid-century modern furniture, you’ll feel right at home on the cozy tufted couches and in the sleek, updated kitchen. The primary bathroom features heated floors, a soaking tub, and a steam shower, and the small outdoor patio is perfect for sipping cocktails or noshing on hors d’oeuvres. The nearby LGBTQ-friendly Boystown has non-stop nightlife (including discos!), as well as plenty of cafes and bistros.

Courtesy Airbnb

Trendy condo in Uptown

Situated on a quiet, tree-lined street, this one-bedroom condo in Uptown offers a tranquil oasis from the downtown noise. The big windows in the Chicago Airbnb let in loads of natural light, illuminating the spacious living room, large dining room, and master bedroom. Conveniently located just six minutes from the Wilson red line, you can quickly zip downtown or to other nearby neighborhoods, including Andersonville, Edgewater, and Ravenswood. The highlight of the area is Montrose Beach, which is steps away from the Airbnb and features a waterfront restaurant, dog beach, bird sanctuary, and miles of walking trails along the water. You’ll also find jazz clubs and vintage theaters, thanks to the area’s history as a booming nightlife destination during the prohibition era.

Courtesy Airbnb

Handcrafted gallery in River West

There’s a reason this River West apartment is called “the gallery.” This three-bedroom condo is part of Open House Contemporary, a collection of homes that feature a curated selection of artwork from America’s emerging artists. Situated in the up-and-coming River West neighborhood, you won’t find better views of the city anywhere. Soak in the cityscape from the living room’s floor-to-ceiling windows and enjoy the amazing artwork that’s peppered throughout (including the lamps and hand-painted murals). Nearby, you’ll find plenty of restaurants and cafes, plus direct access to the “hipster highway” (Milwaukee Ave) and the 606 walking path.

Courtesy Airbnb

Airy condo in Forest Park

If you need a break from the city, stay in this three-bedroom respite in Forest Park. The second-floor condo has a screened-in back porch, a spacious living room, and a large renovated kitchen. Adjacent, tree-lined neighborhood Oak Park is home to adorable shops, eateries, and Frank Lloyd Wright–designed homes. Plus, the L is within walking distance, so you can shuffle downtown in less than 30 minutes.

Courtesy Airbnb

Modern sanctuary in Logan Square

With each room seamlessly transitioning to the next, this one-bedroom condo in Logan Square feels bigger than it really is. Every element is thoughtfully designed and minimalist, from the tucked-away loft bed and built-in desk to the cubby bookcases and the renovated subway tile-lined shower. The highlight is the location, which sits right in Logan Square. Here you’ll find award-winning restaurants (like Giant and Parsons Chicken & Fish), historic landmarks (like the 1915-built Logan Theatre), and dozens of boutiques, vintage music stores, and antique shops.

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