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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. 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. 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. 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. 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.

The master bedroom offers a king bed while the second room has a double bed, making it good for young families or close friends. 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. Guests are able to self check-in here and securely drop bags off if needed. 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.

Just looking around this beautiful loft and its stylish, bohemian decor will make the climb worth it. Best of all, guests have access to the entire main floor of the loft with its many couches and an outdoor deck. In there you have a king bed and an extra single, making it quite a versatile option. Of the options available for renting Chicago penthouses, Airbnb has to be best, especially when you can choose a massive one like this. 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. 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.

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. 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. Air-conditioning, an indoor fireplace, and Wi-Fi just add to the comfort of the apartment. 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. 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.

After an Airbnb in the Chicago suburbs? 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. 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.

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.

One of the friendliest Chicago Airbnbs you can find is this extremely well-rated private room. 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. 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. Of course, renters must go through a screening process to ensure the inexperienced ones wind up with boats that come with captains. Others have the privilege of setting sail on their own, if they wish.

The renting process works much like Airbnb. Renters and owners must accept each other, and owners receive public ratings to help boost their profile. Boatbound was created in to help boat owners offset maintenance costs and to give non-owners the privilege of spending a day at sea. As a special for Memorial Day, veterans can rent a boat for free by downloading the Sandboxx app , which has partnered with Boatbound for the promotion. Skip to content.

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