Skydiving – 15 Best Airbnbs in Chicago, IL (2023 Edition)

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There’s no doubt that Chicago is one of the best cities in the U.S. to visit and explore. Known for its love of sport and food, the city is a hub of culture. To get the most out of your time there, you should be looking at the best Airbnbs in Chicago. Whether you’re after a stylish place to stay or even a 420-friendly Airbnb in Chicago, you’re bound to find what you’re looking for on the platform.

To ensure that these vacation rentals in Chicago are the best Airbnb has to offer, we’ve only selected places with superhosts and/or Airbnb Plus membership. Superhosts are property owners known for their well-reviewed accommodations and quality service, while Airbnb Plus is an exclusive list of properties that the company has inspected in person to verify their quality. With these criteria, you can be confident that you’ve got a good stay ahead of you.

Related: 15 Best Airbnbs in Illinois, USA

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Modern Loft With Free Garage Spot

Anyone looking for the best Airbnb rentals in Chicago should definitely consider this apartment in the neighborhood of Avondale – a central location with shops and restaurants nearby, as well as easy access to downtown.

The first aspect of this Airbnb Plus to jump out at you will be its clear sense of style. The exposed brick and classy, modern decor make the interior immediately welcoming. As a studio apartment, it’s best for solo travelers and couples, who will enjoy the queen bed with a memory foam mattress. The loft makes the most of its limited space with a nice lounge area, a study nook, and even a little balcony.

If you want to prepare your own meals, you’ll be pleased with the apartment’s full kitchen, complete with a gas oven and stove, a dishwasher, and a coffee maker. Other conveniences include Wi-Fi, heating and air conditioning, the option to check yourself in, and free on-site parking.

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Cozy 1-Bedroom Apartment in Wicker Park Area

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

The wonderful artwork throughout the apartment balances nicely with its homey feel, giving you plenty to look at while also helping you relax. It helps that the unit does not have a studio design, providing a bit of space between the queen bed and the large living area.

The tiny kitchenette in the living room corner has a small fridge, microwave, and coffee maker, so you’ll be able to prepare a basic breakfast at least. The apartment also has Wi-Fi, a TV with cable and a Blu-ray player, central heating and air conditioning, a washer and dryer, and free parking.

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Logan Square Apartment With Peaceful Garden Deck

To experience one of the best Chicago Airbnbs out there, look no further than this apartment 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 from 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 friend groups. The master bedroom has a queen bed, while the second bedroom features a set of twin singles, with an additional air mattress should you need it. You can even bring the littlest members of your family, as the apartment includes a portable crib, a highchair, and toys.

Superhost Meighan, who lives upstairs, is happy to answer questions and recommend local attractions. Beyond all the indoor space, you have access to 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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Dog-Friendly Guest Suite in Logan Square

If you don’t need a lot of space for yourself, consider booking a private room rather than a whole apartment. This one lets you enjoy the dining, nightlife, and public transportation connections of Logan Square along with a more social lodging experience.

Superhost Gabrielle offers what feels like a self-contained apartment suite in her Victorian frame house. You get not only a private bedroom with a queen bed, but also your own bathroom, a small back porch, and even a living space with a coffee maker, microwave, and small fridge to make your mornings a little easier.

While the suite is intended for solo travelers or couples, Gabrielle allows some flexibility, offering an air mattress to accommodate a third person upon request. In addition to your private space, you’ll have access to the house’s backyard, so you can even bring your dog. The many other amenities include free snacks, central heating and air conditioning, Wi-Fi, and TV.

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Industrial-Style Loft With Free Garage Parking

While there are many short-term apartment rentals in Chicago, few offer as much style and value as this loft in the quiet, residential area of South Old Irving Park. As one of Chicago’s older neighborhoods, this is a peaceful part of the city to stay in, though a quick train trip takes you to the restaurants and nightlife of Logan Square. 

This renovated loft bears a stylized industrial look, with exposed brick and a surprising art deco ceiling. Sporting a king bed with a memory foam mattress, the separate bedroom makes the loft best for couples or solo travelers. Then there’s the spacious living area with an entertainment center at one end and a full kitchen at the other. The kitchen has everything you need to cook for yourself, including a stovetop, oven, microwave, and full-size refrigerator.

Superhosts Dasha and Owen throw in a lot of extras to ensure you have a great stay. The self-check-in, luggage storage, and free garage spot all contribute to a seamless experience.

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Modern Logan Square Apartment With Free Parking

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

This two-bedroom apartment can comfortably fit four people. With a king bed in the master bedroom and a double bed in the second room, it’s a good rental for young families or close friends. No matter your group dynamic, you’re sure to find the modern, light-filled interior a relaxing environment for your stay. To unwind, you have the choice of the spacious living room or the shared patio in the backyard.

Adding to the convenience for your group, the apartment has a full kitchen with a stove, oven, microwave, fridge, and dishwasher. Other modern comforts such as Wi-Fi, a smart TV with Netflix, a washer and dryer, and air conditioning should help make your stay a pleasant one. You can check yourselves in and securely drop off your bags if needed.

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Private Room in Shared Artist Loft Downtown

If you’re after an Airbnb in downtown Chicago, consider this guest room in the neighborhood of River North – an area famous for its converted warehouses and lofts, artist studios, and upscale bars, nightclubs, and restaurants. You’ll also be a short walk from downtown attractions and the Chicago River’s iconic waterfront.

There’s so much to enjoy about this beautiful loft that you’ll barely mind it being a fourth-floor walk-up. The stylish bohemian decor alone makes the climb worth it. Better still is the phenomenal deck that’s like a secret garden, only with downtown Chicago views all around.

Your private room can sleep up to three people, with the king bed and an extra single making it quite a versatile option. You get your own en suite bathroom for further privacy. You’ll also have access to the entire main floor of the loft, with its many couches and full working kitchen.

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3-Level Penthouse With Skyline View

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

The real headline of this condo is its immense size, spanning over three levels. It can actually sleep up to 14 people, so it’s an amazing deal for big groups or families. In order to fit so many people, it has three bedrooms and assorted sleeping options in its common areas. Large groups will also be pleased that it has 2.5 bathrooms, preventing long lines.

In addition to being huge, the penthouse is both practical and incredibly stylish, with luxurious furnishings that enhance the charms of the historic brick building. It also features a large dining area, a fully equipped kitchen, a cozy living area, a huge bathtub, and amenities such as Wi-Fi and cable TV.

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Victorian Studio Apartment in Old Town

This has to be one of the most pleasant and charming Chicago Airbnbs available. Found in a quiet, leafy part of Old Town, the apartment is close to The Second City, Lake Michigan, and Lincoln Park, with a nice selection of cafes and restaurants nearby too.

While this is technically a studio apartment, the design includes a number of partitions, which makes it feel more spacious. Still, with just a queen bed for sleeping, the space is only meant for one or two guests. A particularly charming aspect of the apartment is its restored Victorian interior, with homey touches like an indoor fireplace. 

Not everything about the apartment is old-fashioned, of course. It provides modern comforts such as air conditioning, Wi-Fi, and a kitchen with a stove, oven, microwave, dishwasher, and fridge. As a ground-floor apartment with no steps inside or out, it’s also convenient for those with accessibility concerns.

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West Town Apartment With Private Garden

Some Airbnbs in Chicago force you to compromise on space, style, or location – but not this apartment in Noble Square, where you get two bedrooms, a peaceful garden, and an interesting neighborhood to explore. Noble Square is a lively part of Chicago with a diverse selection of places to eat and shop, as well as transport connections to get you downtown.

You’ll be delighted with all the space you get in this Airbnb Plus, making it an excellent choice if you’ll be in Chicago for a while. The apartment is best for solo travelers and couples, but 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.

While the apartment has a stylish living room and a modern kitchen with everything you need for cooking, the garden is the main attraction here. 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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Private Guest Condo Near Evanston

Looking for an Airbnb in the Chicago suburbs? Check out this wonderful home in the multicultural suburb of West Ridge, a diverse residential area that offers a nice change of pace from the inner city. It’s quite simple to take the train to downtown Chicago from here, passing some of the city’s coolest neighborhoods on the way.

The rental unit is one floor of the house, with superhosts D and B living upstairs, but you’ll have complete privacy. This Airbnb Plus features two bedrooms, each with a queen bed, making it suitable for young families or two couples on vacation together. The bedrooms, living room, and dining area all have a tastefully modern look, with occasional touches of a fun cattle-ranch theme.

Between the living room and dining area sits the condo’s full kitchen. Behind the breakfast bar, you’ll find a stove, oven, microwave, fridge, and dishwasher that make self-catering a cinch. Other nice amenities include self-check-in, free parking, and Wi-Fi.

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Guest Room in Andersonville Home

One of the friendliest Chicago Airbnbs you can find is this extremely well-rated private room in Andersonville, a quaint neighborhood with a strong community vibe and lots of great local businesses. Even though it’s quite far to the north, you can reach the downtown area by train easily enough from here.

The rental is a private room in the home of superhosts Mat and Randy. This room can sleep two people in the queen bed and enjoys plenty of light from its large window. It also provides a minifridge, cable TV, Wi-Fi, and a lock on your bedroom door, making this an easy place to relax and unwind. 

You’ll share the bathroom with the rest of the house but receive your own towels. You’ll also have access to the kitchen, where you can prepare meals or just get tea and coffee, and the laundry room – not to mention the huge deck in the peaceful garden.

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Contemporary Home in Logan Square

This gorgeous one-bedroom home is the perfect Airbnb in Chicago for couples or solo travelers. 

The interior of this Airbnb Plus has chic decor that lends a cozy feel, including exposed wood and colorful accents. In the living room, you can unwind on the sectional sofa and stream your favorite shows on the smart TV. The kitchen features a lovely exposed brick wall, stainless steel appliances, and an espresso machine. 

In the master bedroom, you can sink into the plush king-size bed, complete with a memory foam mattress for a good night’s sleep. There is also a small desk for remote work, books, and an en suite bathroom. The second bedroom has a comfortable double bed and room-darkening shades. 

You can enjoy a relaxing rinse in the first bathroom’s walk-in steam shower with a rain showerhead, while there is a tub/shower combo in the second bathroom. Those traveling with little ones will be happy to hear the home is also equipped with a travel crib, a baby bath, and a washer and dryer. 

You’ll have access to the backyard, where you can relax with a glass of wine in the open air or let the little ones run around. Free street parking is available.

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Private Room in Uptown Artist’s Apartment

Feel like supporting a nonprofit through your choice of Airbnb in Chicago? If you rent this private room in the heart of the Uptown Entertainment District, the proceeds from your stay will go toward local neighborhood causes. You’ll also be in a great spot to explore everything Uptown has to offer, including its famous food scene and live music, and just three train stops away from Wrigley Field.

This apartment inside an old Chicago greystone building belongs to superhost Oliver, who rents 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 double bed.

Beyond the bedroom, you’ll have access to a shared bathroom and the kitchen, which is stocked with local tea and coffee. You also have options to use the Wi-Fi, cable TV, and laundry facilities, but the biggest bonus is experiencing Oliver’s friendly hospitality and admiring all the artwork.

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Lincoln Park Apartment

If you’re looking to rent an Airbnb in Lincoln Park, Chicago, consider staying at Beth’s gorgeous one-bedroom flat. 

This Airbnb Plus boasts stylish decor and exposed brick and wood walls that create a beautiful space. In the bedroom, you can close the room-darkening shades and enjoy a nap in the comfortable queen-size bed. The bathroom has a spacious walk-in shower, stocked with complimentary body wash, shampoo, and conditioner. 

After a day exploring the city, you can kick back on the massive sectional sofa and stream your favorite shows or movies on the smart TV. The couch can fold out to become two daybeds, making this Airbnb suitable for up to four guests. The kitchen features stainless steel appliances, including a SMEG fridge and a washer and dryer. You can enjoy your meals at the large wooden dining table. 

The home is a short walk from restaurants and bars, and O’Hare International Airport is only a 20-minute drive away. You also get free street parking.

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

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