The Best Airbnbs and Vacation Rentals in Chicago, Illinois

The Cloud Gate sculpture, also known as The Bean, has become a famous Chicago monument
The Cloud Gate sculpture, also known as The Bean, has become a famous Chicago monument | © JLImages / Alamy Stock Photo
Photo of Nick Dauk
7 April 2021

Skyscrapers dot the shore of Lake Michigan in the famous Windy City. Stroll through the Millenium Park, browse multi-million dollar artwork at the Art Institute of Chicago, or admire the view from the top of the 360 Chicago Tower. Chicago is pedestrian and cyclist friendly, and with a fantastic subway system, you can effortlessly venture into every corner of the city. Staying at a vacation rental is the next best thing to living in the Windy City, and these self-catering stays will make you feel right at home.

LEVEL Chicago – Old Town

Short-term Rental
Map View
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Courtesy of LEVEL Chicago – Old Town / Expedia
Whether you want to hit the beach, see “the bean”, or try the best pizza parlour in Old Town – hello, Happy Camper Pizzeria – LEVEL River North’s aparthotel puts you within minutes of it all. The in-room washer and dryer are super convenient for rinsing off your swimsuit after a day spent at Oak Street Beach or in the onsite pool. These deluxe rooms, which sleep up to four, are also pet friendly, while the seven-acre (3ha) doggy heaven that is Seward Park is only a block away.
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Sonder - The Plymouth

Short-term Rental
Map View
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Courtesy of Sonder - The Plymouth / Booking.com
You’re always in The Loop at Sonder’s The Plymouth apartments. Ranging from singles to three-bedrooms, which sleep as many as eight guests, these suites have full kitchens alongside areas to work, relax, and dine. A communal fitness center and outdoor terrace are great perks, but the best way to get your body moving is by walking a few blocks east to the Lakefront Trail adjacent to Grant Park. Though there is no parking onsite, the Harold Washington Library-State/Van Buren subway station is only a block from your room.
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Kasa Chicago South Loop Apartments

Short-term Rental
Map View
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Courtesy of Kasa Chicago South Loop Apartments / Expedia
In town for a Bears’ game? These apartments in Chicago’s South Loop will help you kick off an awesome vacation. One- to three-bedroom suites have full kitchens, so you can whip up snacks to chow down on while setting your fantasy lineup. Tinker around a bit more with coffee and city views on the terrace, then head down to nearby Soldier Field. Grab a hotdog from Kim & Carlo’s on the way, but if you can’t grab tickets to the game, catch all of the action at the late-night sports bar South Loop Club, just a Hail Mary away from the comfort of your bed.

Sonder at 943 Crosby

Short-term Rental
Map View
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Courtesy of Sonder at 943 Crosby / Booking.com
Trade lakefront for riverside with a stay at one of the smoke-free apartments in Sonder at 943 Crosby, right around the block from the Chicago River. Here you’ll find stylish queen and king suites that can sleep up to four. Must-visit spots, like the Chicago Water Tower and John Hancock Center, are less than ten-minutes away by car, which means even peak rush hour traffic won’t eat into your sightseeing. Prefer to save gas and ride the rails? The Chicago Station, serving both Brown and Purple lines, is just over a half-mile to the south.

Sonder at South Wabash

Short-term Rental
Map View
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Courtesy of Sonder at South Wabash / Booking.com
Staying in Sonder at South Wabash apartments offers the creature comforts that you can’t live without – even on vacation. A gym, washer and dryer, full kitchen and infant bed are all included in your stay. Whether you need a two-bedroom that sleeps a family of six or a cosy studio for you and your beau, these apartments are perfectly located less than a 30 minute walk from kid-friendly attractions like the John G. Shedd Aquarium, Grant Park, and the Field Museum of Natural History.
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  • Kasa Chicago River North Apartments

    Short-term Rental
    Map View
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    Courtesy of Kasa Chicago River North Apartments / Expedia
    Your shopping spree begins as soon as you roll out of bed in this gorgeous apartment complex, only three blocks away from the Magnificent Mile. The Whole Foods onsite lets you get the most out of the full kitchen, but there is a Starbucks Reserve Roastery and Giordano’s around the corner, if you want to fuel your vacay with fresh coffee and humongous deep dish pizza slices. Apartments range from studios that sleep three to two-bedrooms for six, but all include a comfortable living room with amazing downtown views.
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    Wrigleyville Coach House

    Homestay
    Map View

    A hugely sought-after spot in bustling Wrigleyville, this 1894 red-brick coach house is full of surprises. Set back from the street, it’s a little rustic oasis, and has recently been renovated with plenty of contemporary features. This place is ideal for families, with four bedrooms and room for eight, there are plenty of neat details the kids will love, including a secret play space and a walk-in toy closet. With its prime location near Wrigley Field, the park, zoo and beaches, this Airbnb is a solid family vacation option.

    Modern Loft, River West

    Homestay
    Map View

    This River West spot is more than just a loft space. It’s the pad for you if you’re looking for a place to unwind, hang out and enjoy some quality time with friends or family. A surround-sound cinema room, jacuzzi and pool table add to its appeal, along with cool hanging chairs and an inviting industrial-retro aesthetic. Sleeping up to eight guests split across four bedrooms, and with three bathrooms, this is luxury lofting at its finest. And while it is tempting to just stay in the space and chill, there are plenty of attractions within walking distance in the nearby Wicker Park and Bucktown neighborhoods.

    This is an updated version of an article originally written by Tara Gardner, with additional reporting by Josh Taylor.

    These recommendations were updated on April 7, 2021 to keep your travel plans fresh.

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