15 Best Airbnbs in Chicago, IL (2022 Edition)

There’s no doubt that Chicago is one of the best cities in the U.S. to visit and explore. The city is a hub of culture and is known for its love of sport and food. To get the most out of your time in the city, be it on a vacation or a staycation, the best Airbnbs in Chicago are where you need to be looking. Whether you’re after a stylish place to stay or even a 420 friendly Airbnb in Chicago, Airbnb has something for travelers of every stripe.

To ensure that these vacation rentals in Chicago are indeed the best Airbnb has to offer, only places with superhosts and/or those who are part of Airbnb Plus have been selected. Superhosts are Airbnb hosts known for their well-reviewed quality accommodation and service. Meanwhile, Airbnb Plus is an exclusive list of Airbnbs that have been verified through in-person inspections to ensure their accuracy. By using these criteria, you can have confidence that you’ve got a good stay ahead of you.

Related: 15 Best Airbnbs in Illinois, USA

Modern Chicago Loft with a Complimentary Garage Spot

Those looking for the best Airbnb rentals in Chicago will definitely want to take a moment with this apartment. Situated in the neighborhood of Avondale, this Airbnb Plus provides you with a central location that has shops and restaurants nearby, as well as easy access to downtown.

The first thing to jump out at you with this Chicago loft will be its clear sense of style. Inside there’s plenty of exposed brick and classy, modern decor that makes the space immediately inviting. Since this is a studio apartment, couples and solo travelers will find themselves best suited to staying here. There’s plenty of comfort offered here thanks to the queen bed with memory foam mattress, while the studio makes the most of its space with a nice lounge area and even a little study space.

Guests wanting to prepare their own meals will be pleased with the apartment’s full kitchen, complete with a gas oven and stove, dishwasher, and coffee maker. Other modern amenities include Wi-Fi, heating, and air-conditioning, and the option for self check-in. Finally, guests also have access to a little balcony and free on-site parking.

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Beautiful Airbnb in Great Location

With a comfortable and cozy interior, other vacation apartments for rent in Chicago could learn a lot from this great Airbnb. Located in the area of Wicker Park and Noble Square, the apartment puts guests nice and close to shops, cafes, and public transport for getting into downtown.

What’s nice about this one bedroom apartment is how the wonderful artwork everywhere balances with its homely feel. The decor effortlessly helps you relax while also giving you plenty to look at. It helps that this apartment does not have a studio design, providing a bit of space between the queen bed in the bedroom and the large living area.

One drawback of this Airbnb is that it only has a small kitchenette in the living room corner. With a small fridge, microwave, and coffee maker, you will be able to prepare a basic breakfast at least. Besides that, this apartment also features a TV with cable and a Blu-Ray player, central heating, air-conditioning, a washer/dryer, free parking, and Wi-Fi.

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Best in Chicago, Private, Amazing Garden Space

To experience one of the best Chicago Airbnbs out there, look no further than this apartment. Found in Logan Square, a popular historic neighborhood full of restaurants, cafes, cocktail bars and craft beer taverns. You’ll love spending time in this leafy part of the city, especially since it’s an easy train journey to both O’Hare International Airport and downtown.

This beautiful, spacious apartment can sleep up to five guests, making it a great option for families and groups of friends. In the master bedroom there’s a queen bed and the second room features a set of twin singles, with an additional air mattress should you need it. Parents with little ones will also have access to a portable crib, a high chair, and kids toys.

You also have superhost Meighan living upstairs. Megan is happy to help with questions and provide local recommendations should you need them. Beyond all the indoor space, guests also have a serene and private back deck, as well as a garden shared with Meighan below. Other benefits of staying here include a full kitchen, fast Wi-Fi, ample street parking, and laundry facilities.

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Logan Square Vintage Deluxe Suite

When you don’t need a lot of room and are seeking a more social experience, consider booking a private room rather than getting a whole apartment to yourself. This one is situated in trendy Logan Square, a neighborhood bursting with great dining and nightlife, while also enjoying super convenient public transportation connections.

Superhost Gabrielle offers guests what feels like a self-contained apartment suite in her Chicago Victorian frame house. Not only do you get a private bedroom with a queen bed, but you also get your own bathroom, a small back porch, and even a living space. On top of that, there’s a coffee maker, microwave, and small fridge for your use, which will probably make your mornings a little easier.

While best suited to solo travelers or couples, Gabrielle allows for some flexibility with bookings. There is an air mattress which can accommodate a third guest, and the house is dog friendly, so you can bring your pet too. Besides their own space, guests enjoy access to the house’s backyard, as well as lots of amenities like free snacks, central heating and air-conditioning, Wi-Fi, and TV.

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Industrial Style Chicago Loft with Free parking

While there may be many short term apartment rentals in Chicago, few offer visitors as much style and value as this loft. Located in the quiet, residential area of South Old Irving, this is one of the older neighborhoods of Chicago. This makes it quite a peaceful part of the city to stay in, while a quick trip on the train takes you to the restaurants and nightlife of Logan Square. 

Recently renovated, this one bedroom loft bears a stylized industrial look to it, with exposed brick and a surprising art deco ceiling. In its separate bedroom there is a big king bed with a memory foam mattress, best suited to couples or those traveling solo. Then there’s the spacious living area with an entertainment center on one end and a full kitchen on the other. Equipped with a stovetop, oven, microwave, and full-sized refrigerator, it has everything you need to cook for yourself.

Superhosts Dasha and Owen throw in a lot of nice touches to ensure you have a great stay. From self check-in to luggage storage and a free garage spot, they aim to make your experience as seamless as possible.

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Hip Chicago Apartment – Free Parking Spot Included

If you’re planning to rent an apartment in Chicago for your vacation, don’t miss this fantastic one in an ideal part of the city. Found in the popular neighborhood of Logan Square, this is one of the coolest parts of Chicago, offering plenty of character along with some great bars and restaurants.

Within this two bedroom apartment you’ll be able to comfortably fit four people. The master bedroom offers a king bed while the second room has a double bed, making it good for young families or close friends. No matter who’s staying, they’re sure to find the modern, light-filled interior of this recently renovated Chicago Airbnb to be a relaxing environment during their vacation. To unwind, you have the choice of the snug living room or the shared patio in the backyard.

For your convenience, the apartment features a fully-equipped kitchen with a stove, oven, microwave, fridge, and dishwasher. It has other modern comforts like Wi-Fi, a smart TV with Netflix, a washer/dryer, and air-conditioning to make your stay a pleasant one. Guests are able to self check-in here and securely drop bags off if needed.

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Shared Artist Loft Own Private Room

If you’re after an Airbnb in downtown Chicago, consider staying in a private room in this awesome loft. Situated in the neighborhood of River North, this area is famous for its converted warehouses and lofts, artist studios, and upscale bars, nightclubs, and restaurants. You’ll also be a short walk from the Chicago River with its iconic waterfront, plus all the attractions around downtown.

There’s so much to enjoy about this fantastic artist loft that you won’t mind it being a fourth floor walk up. Just looking around this beautiful loft and its stylish, bohemian decor will make the climb worth it. Then there’s the phenomenal outdoor deck that’s like a secret garden, only with views of downtown all around. Best of all, guests have access to the entire main floor of the loft with its many couches and an outdoor deck.

Then there’s your private room, which is able to sleep up to three people. In there you have a king bed and an extra single, making it quite a versatile option. You also have your own ensuite bathroom, so there’s no need for sharing. Other guest amenities include use of the loft’s full working kitchen and Wi-Fi.

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Three Level Skyline View Chicago Penthouse

Of the options available for renting Chicago penthouses, Airbnb has to be best, especially when you can choose a massive one like this. Located between River West and Noble Square, you couldn’t ask for a better area from which to get to know Chicago. Downtown is just a quick trip away, but the local area is nice and quiet. Plus, there are grocery stores, restaurants, and bars all close by.

The real headline with this condo though is its immense size, as this penthouse actually spans three levels. Even crazier, it’s possible to sleep up to fourteen people, making it perfect for big groups or families. In order to fit so many people, it has three bedrooms and an assortment of additional sleeping options in its common areas. Large groups will also be pleased that it features 2.5 bathrooms so there won’t be any long lines.

Beyond being huge, this penthouse apartment is both practical and incredibly stylish. The furnishings throughout are luxurious and enhance the charms of this historic Chicago brick building. Guests also have a large dining area, a fully equipped kitchen, cozy living area, a huge bathtub, and amenities like Wi-Fi and cable TV.

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Charming Apartment in Old Town

Full of charm, this has to be one of the most pleasant and humble Chicago Airbnbs available. Found in a quiet, leafy part of Old Town, this apartment is very close to The Second City, Lake Michigan, and Lincoln Park, with a nice selection of cafes and restaurants nearby too. Many people actually say that this is the best part of Chicago for tourists to stay in.

An interesting aspect of this apartment is its restored Victorian interior that makes it feel homely and inviting. While technically a studio apartment, the design of this Airbnb includes a number of partitions, which makes it feel more spacious. That said, the apartment is only meant for up to two, with just a queen bed for guests.

Not everything about this apartment is old-fashioned, with the modern kitchen featuring a stove, oven, microwave, dishwasher, and fridge. An important thing to note about this Airbnb is that it’s a ground floor apartment with no steps inside or out, making it a smart choice for those with accessibility concerns. Air-conditioning, an indoor fireplace, and Wi-Fi just add to the comfort of the apartment.

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The Noble Farmhouse, Sunlit with Private Garden in West Town

Some Airbnbs in Chicago and other big cities make you feel like you need to trade-off comfort, style, or location. Not this apartment in Noble Square though, where you get a stylish place with a peaceful garden and an interesting neighborhood to explore. Noble Square is a lively part of Chicago with a diverse range of places to eat and shop, as well as solid transport connections into downtown.

With this Airbnb Plus you’ll be delighted with all the space you have, making it an excellent long term choice if you’ll be in Chicago a while. The apartment is best suited to solo travelers and couples, although it can sleep three if you use the sofa bed in the second bedroom. A queen bed with a memory foam mattress awaits in the master bedroom, ensuring a restful night’s sleep.

While the apartment has a stylish living room and modern full kitchen with everything you need, it’s the garden that many guests fall in love with. Surrounded by greenery, it’s a little oasis that’s even within range of the Wi-Fi so you can easily work or chill out there all day.

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Feel at Home in Chicago, with Parking, Steps from Evanston

After an Airbnb in the Chicago suburbs? Then be sure to take a look at this wonderful home in the city’s north. Situated in the multicultural suburb of West Ridge, this is a diverse residential area that offers a nice change of pace from the inner city. It’s also quite simple to take the train into downtown Chicago, passing some of the city’s coolest neighborhoods on the way.

Renting this condo you’ll be occupying one floor of the house, with superhosts D and B living upstairs. But you also have complete privacy in this Airbnb Plus. The condo features two bedrooms, each with a queen bed, making it suitable for young families or two couples on vacation together. Everything from the bedrooms to the living area and dining area has a tasteful, modern look to it, with occasional cattle ranch themed accents here and there.

Sitting between the living area and dining area you’ll find the condo’s full kitchen. There, behind the breakfast bar is a stove, oven, microwave, fridge, and dishwasher that will make self-catering a cinch. Other nice touches include self check-in, free parking, and Wi-Fi.

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Andersonville – Perfect Location!

One of the friendliest Chicago Airbnbs you can find is this extremely well-rated private room. Located in the relaxed and quaint neighborhood of Andersonville, there’s a strong community vibe here and lots of great local businesses. And even though it’s quite a way to the north, it’s easy enough to reach the downtown area by train.

Staying here, you’ll be renting a private room in the home of superhosts Mat And Randy. The room can sleep two people with a queen bed and enjoys plenty of light thanks to its large window. Here, guests have access to a mini fridge, cable TV, and Wi-Fi, making it an easy place to relax and unwind. Bathroom facilities are shared and guests are provided with towels.

Beyond your room, you’ll also have access to the kitchen where you can prepare meals or just get tea and coffee, not to mention the huge deck in the peaceful garden. There’s also access to laundry facilities here and a lock on your bedroom door for your privacy.

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Archways Apartment Across from Lincoln Park Zoo

This Airbnb in Lincoln Park Chicago is a great pick for those wanting somewhere both stylish and in a great location close to attractions. The Airbnb sits just across the road from the Lincoln Park Zoo and is close to great spots like the beaches along the Gold Coast. What’s more, it couldn’t be easier to visit downtown and the Magnificent Mile.

With this Airbnb Plus, you’ll be staying in a gorgeous apartment inside a historic building that was once a hotel. Splashes of color liven up this well-appointed two bedroom apartment, making the space especially welcoming and easy on the eyes. Each bedroom comes with a queen bed, while the master bedroom has an ensuite. There is also a second bathroom as well, fitted with a bathtub should you need it. Parents with young children will find this place a good fit as there’s a travel crib and other kid-friendly equipment available.

Guests will be pleased to know that the apartment comes with a large and fully-equipped kitchen so that you can self-cater. Other bonuses here include self check-in, free street parking, Wi-Fi, and TVs in each room with Netflix and HBO GO.

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Classic Chicago Greystone Apt

Feel like supporting a great cause through your choice of Airbnb in Chicago? Then stay at this private room in Uptown and the proceeds from your stay will go towards local neighborhood causes. Found right in the heart of the Uptown Entertainment District, you’re in a great spot for exploring everything Uptown has to offer, from its food scene to live music. Plus, Wrigley Field is just three train stops away.

Inside an old Chicago greystone, this artist’s apartment belongs to superhost Oliver, who is renting out a private room that sleeps two. Throughout the apartment you’ll see an incredible range of contemporary artwork and carefully considered modern decor. Even your room has a rotating selection of artwork hanging over the full-sized bed.

Beyond the bedroom, guests have access to a shared bathroom and the kitchen area, which is fully stocked with local tea and coffee. But there’s also Wi-Fi in the apartment and the possibility of watching cable TV and using Oliver’s laundry facilities. Really the biggest bonus though is experiencing Oliver’s hospitality and admiring all the artwork.

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Private Room/Bath Wicker Park, Free Street Parking

It may not always be easy to find a cheap Airbnb in Chicago, but this private room is definitely an option that’s great value. Situated in West Wicker Park, this area is just a couple of train stops to the restaurants and nightlife of Logan Square. It’s also very easy to get the train into downtown Chicago or over to O’Hare International Airport.

In this Airbnb, you’ll be a guest of superhost Meta in her gorgeous home. It’ll actually be hard to believe that you could stay in such a nice place for such a reasonable rate. But yes, staying here you’ll indeed have a private bedroom as well as a bathroom all to yourself. The room sleeps two people with a twin-size daybed, however a trundle bed can be added so that guests have separate beds. Both the bedroom and the bathroom have locks, ensuring your privacy.

Other than your personal space, guests also share access to the kitchen, living room, and back deck. The kitchen is fully-equipped allowing you to cook meals if you like. Over in the living room you’ll find a smart TV with cable and Netflix. Additional perks include Wi-Fi and free street parking.

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No matter how long you’re staying in the city, we’re sure that these Airbnbs in Chicago will only enhance your time there. Safe travels and enjoy The Windy City.