There are numerous things Chicago is famous for, but its North Side neighborhood is one of the less widely known destinations. The North Side is one of the oldest parts of the city of Chicago. It has gone through different crises economically, and turmoils such as the tragic fire in the city of Chicago in 1871. Needless to say, it has survived over the course of time and has a long history worthy to be recognized. It has now become one of the most successful and vibrant cities. And as a testament to this newfound success and betterment of livelihood in the North Side, numerous attractions, architecture, and buildings have been established for the benefit of the city’s locals and to encourage tourists to come and explore the distinct city of Chicago. For tourists who would love to experience this beautiful city and immerse themselves in its rich culture, here are some accommodations you can stay in as you enjoy all the attractions and check out the restaurant, bars, clubs, and dinner cruises in Chicago. Scroll down to check out the best Airbnb vacation rentals in North Side, Chicago.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 14, 2024.
1. Sophisticated yet chic long term rental
This stylishly decorated two-bedroom apartment rental in North Side, Chicago, is perfect for those seeking comfort and convenience. The fully stocked kitchen is equipped with all the essentials, ensuring hassle-free meal preparation. The living room exudes warmth with plush sofas, a chic coffee glass table, and a TV for relaxation. A dedicated workspace caters to professionals or students working from home, while reliable WiFi keeps you connected.
Stay comfortable throughout the seasons with the air-conditioning system. Families with little ones will appreciate the added convenience of a travel cot. On-street parking is available for residents. Ideal for long-term rental, this charming property promises a delightful living experience for anyone seeking a harmonious blend of style and functionality.
Chicago, Illinois, United States
5.59 km (3.5 mi) from 875 North Michigan AvenueSuperhostAccommodates: 4
Top guest reviews
Amenities & Room:
the video describing how to enter the apartment complex was very helpfulhad some trouble with wifi but hosts were very responsive in getting us on a connecting networkthe beds were extremely comfortableit got pretty chilly in the city but the apartment was very well heatedCleanliness:
but the place is clean with real chicago charm and well tended totheir place was very cleana very cozy and clean stay it was easy to find and communication was received wellclean comfortable & had what we needed for our stayhome was very clean and comfortableHost:
the host was amazing and attentivehosts are very responsive in communicating and left simple instructionsthe owners were very responsive and attentive before during and after the stayvincent and sofia were responsive to all our questionsvincent & sofia we’re very friendly and have clear instructions on how to get in & get outRead more reviewsLocation:
the location was goodwe loved the locationgreat location comfortable bedsapartment location was just perfect - close to restaurants shops & public transportationgreat apartment in a great location
2. Elegant and classy apartment (from USD 61)
This charming one-bedroom, one-bathroom Airbnb home rental is ideal for a cozy and comfortable living experience. The living room welcomes you with a plush sofa and a flat-screen TV, perfect for relaxing after a long day. Stay connected with the provided WiFi throughout the space. The fully stocked kitchen offers all the essentials for convenient meal preparation. Enjoy a pleasant stay with the property’s full air-conditioning.
For added convenience, the launderette, shared with fellow tenants, ensures hassle-free laundry days. Embracing an urban lifestyle, this property boasts a prime location with restaurants and cafes nearby, offering delightful dining options. Public transport is within walking distance, making commuting a breeze. Enjoy the perfect balance of comfort, convenience, and accessibility in this delightful abode.
Chicago, Illinois, United States
6.1 km (3.8 mi) from 875 North Michigan AvenueSuperhostAccommodates: 2
Top guest reviews
Amenities & Room:
excellent stay at jaden’s apartmentCleanliness:
lakeview is a great neighborhood and jaden’s clean welcoming place was perfect for a long weekendRead more reviewsHost:
he was friendly giving us tips and really responsivejaden was a great hostall instructions before arrival were easy to follow and he was extremely responsivevery responsive before during and after the stay
3. Chic urban apartment by the Magnificent Mile (from USD 275)
Check out this two-bedroom apartment for rent if you’re looking for a place to stay in the Windy City. The two-bedroom apartment features a modern design that is spacious, stylish, and bright to make your stay comfortable. It can sleep up to four guests and features amenities like cable TVs, WiFi, and a fully equipped kitchen. It is located close to the Magnificent Mile, the city’s vibrant commercial district where you can find posh shops, great restaurants, cool hangouts, and iconic landmarks.
Chicago, Illinois, United States
719 meters (0.5 ft) from 875 North Michigan AvenueSuperhostAccommodates: 4
Top guest reviews
Amenities & Room:
the apartment was stocked with amenities super clean and so cutethe apartment was so beautiful and felt comfortable it was stocked full of essentials for us to usewe had a wonderful stay at tatiana & roupen’s beautiful apartmenti can't say enough good things about this place and was so comfortable for a party of 4Cleanliness:
it’s clean and fashionablewe found the place extremely clean and organizedthis apartment was gorgeous and spotlessbeautifully decorated with great amenities extremely clean and excellent communication with hostsspotless clean and tatiana is amazing — and great location thank you tatianaHost:
the hosts are also very friendlyour hosts tatiana & roupen were the bestthey were helpful when one part of our party had a problem with the keyshosts checked in to make sure we were happy and even offered early check-in without us askingthey are wonderful hostsRead more reviewsLocation:
apartment was cute and great locationa lot of food options near by and great locationthis is the cutest apartment in the best location close to everythingthe location was perfect half a block off of magnificent mileit’s in the middle of chicago so perfect if this is the location you need
4. Chic downtown condo in the heart of River North nightlife
This condo offers guests a perfect blend of convenience and comfort. Its location in the heart of River North ensures convenience as you’re going to be close to everything—from business centers to nightlife. Comfort-wise, the unit is impeccably designed, furnished, and decorated to ensure you’ll have a relaxing time here. It consists of two bedrooms, two bathrooms, a living room, an eat-in nook, an office space, and a kitchen, all equipped with modern amenities for all your needs and wants.
Chicago, Illinois, United States
897 meters (0.6 ft) from 875 North Michigan AvenueAccommodates: 6
Top guest reviews
Cleanliness:
warm and wonderful and very clean apartmentit was very clean and check in was easyit was very clean and easy access in and outclean spacious and great locationsparkling clean with several thoughtful touches it is the perfect chicago retreatHost:
rebecca was a wonderful hostrebecca is a great host responsive and super helpfulshe was extremely responsive and helped my friends and me sort out a unique situationshe could not have been any more responsive to our needs and was very pleasant to deal withgreat host great locationRead more reviewsLocation:
a cute place in a great location in river northlocation was great toothe location was absolutely perfect and very centralthe location was terrific with easy access to restaurants and stores like cvsamazing place in a awesome location
5. Comfy condo conveniently close to many Chicago attractions (from USD 349)
Convenience is the keyword for this two-bedroom condo for rent in North Side, Chicago, that can sleep up to six guests. Located just seconds from Lake Michigan and Magnificent Mile and steps away from The Drake Hotel and Oak Street Beach, this home offers quick and easy access to some of Chicago’s finest attractions. Complimenting this convenience, the home boasts a tranquil rooftop with a magnificent view of the lake, comfy king- and queen-sized beds, a custom chef’s kitchen, and floor-to-ceiling windows with a great view.
Chicago, Illinois, United States
270 meters (0.2 ft) from 875 North Michigan AvenueSuperhostAccommodates: 6
Top guest reviews
Amenities & Room:
the view from the living room is stunningthe view from the living room and bedrooms are absolutely stunningthe rooms are nice and some amenities are provided; hand towels bath towels etcthe place is spacious clean cozy and loved the view of the laketwo nice and cozy rooms to accommodate you for a nice nights sleepCleanliness:
well worth it clean comfortable beds and pillowssuper easy check in and the apartment was very clean and spaciousthe property is beautiful and very cleanthis place is outstanding checking-in was a breeze it’s clean and comfortablethe place was easy to find easy to access and wonderfully cleanHost:
thank you for being such wonderful hosts :)hosts are very responsivewonderful hosts and even better citythey were very informative made me feel really comfortablereally nice and even a better hostRead more reviewsLocation:
the location was greatwalking distance to all sorts of restaurants and magnificent mileall of my favorite downtown chicago places are walking distancegreat location exactly like the picturesgreat location to walk around shop and see the city
6. Modern one-bedroom apartment
This modern, minimalist apartment is well-maintained and strives to give guests a hassle-free stay with their 24-hour front desk service and daily housekeeping. The ambiance of the apartment is welcoming and comfortable with a queen-sized bed and two twin-sized beds and it sleeps a total of four guests, perfect for families and friends. The building in which the apartment is located features a cafe and restaurant that guests can have access to at their own convenience.
Chicago, Illinois, United States
1.09 km (0.7 mi) from 875 North Michigan AvenueAccommodates: 4
Top guest reviews
Amenities & Room:
really cool room and the cafe has great coffee and donutsCleanliness:
place was clean and newclean rooms and facility in generalvery nice clean place for a short staythe room was very cleanalso the rooms are super clean and comfortable to stay and chillRead more reviewsLocation:
great location near lin a good locationgreat place in good locationthis place has a very interesting style that stays true to the fieldhouse themeit was a great and unique place to stay
7. Cozy and clean apartment
This one-bedroom apartment is well-maintained and cozy for guests to have a wonderful stay. Perfect for a business trip or for leisure time since it’s near O'hare Airport and walking distance to bus stops. This spacious apartment can accommodate four guests, has a large living room with a comfortable sofa and a flat-screen TV with Netflix, a working table and a chair for guests who are on a working holiday, and a kitchen equipped with the necessary appliances. Internet connection is also available for free.
Chicago, Illinois, United States
14.15 km (8.8 mi) from 875 North Michigan AvenueAccommodates: 4
Top guest reviews
Amenities & Room:
you can sleep two easily as it provides one bedroom and one sofa bedoverall great spacious place with a full sized bed and a foldable couchthe place was comfortable and roomy and actually bigger than expectedi learned a word in polish played darts and poolnice basement apartment with fully equipped kitchen bathroom and bedroomCleanliness:
very clean and privatevery clean and nicethe space was very clean and comfortableapartment was clean and cozybathroom was cleanHost:
the hosts are very generous and kindhost was very friendly and accommodatingand both hosts were very helpful and informationalthe hosts were also very responsive when we had questions or needed extra toilet paperpros: hosts were responsive and fairRead more reviewsLocation:
good location not too far from bus stopslocation was pretty goodwish it was closer to public transportation but still a good staygood location if you are coming in from the airportgreat spot great location great deal
8. Cozy apartment in great location
This vintage-style apartment is in the heart of the bustling streets of the city. It features a comfortable queen-sized bed and a sofa that folds down into a bed, and a small kitchen that’s equipped with the necessary appliances. The apartment has an elevator so it’s no problem for guests who have luggage. Also, the apartment owner welcomes pets as long as they are well-trained. The apartment is a walking distance to shopping centers, nightlife and restaurants, so it might get a little noisy at night. It’s best to bring earplugs if you’re a light sleeper.
Chicago, Illinois, United States
937 meters (0.6 ft) from 875 North Michigan AvenueTop guest reviews
Amenities & Room:
little bit of a small apt but perfect for 1-2 people for a short staygreat comfortable place to stayCleanliness:
very clean quiet buildingthe place was very clean and very beautiful on the insidethe place is very cleanapartment is clean serviceable; would stay againit’s clean and in a wonderful locationHost:
the host is greatgreat host - easy to communicate - quick responsesnice apartment and great hostgreat communicative and flexible hosthost responded quickly and was great on such a short noticeRead more reviewsLocation:
location is great walking distance to many popular spotsgreat location for a quick staygreat location would go backgreat location with plenty to do within easy walking distancegreat location with everything you need
9. Two-bedroom apartment in an upscale neighborhood
This apartment has a great value for money, especially for tourists traveling on a budget even if situated in an upscale neighborhood with residential buildings and high-rise condos. This apartment is perfect for couples who are looking to have quality time. It’s clean and well-maintained and features a small dining table for a quick snack and a compact kitchen with the necessary appliance. Guests love booking this apartment because of its great location near popular restaurants, nightlife and shopping. The area is private and comfortable and the owner is a great host and is available for inquiries and assistance.
Chicago, Illinois, United States
968 meters (0.7 ft) from 875 North Michigan AvenueTop guest reviews
Amenities & Room:
the room isn't extra special but the area is fantasticwould have been nice with a tvpretty basic amenities but clean comfortable and easy to check in and outi had a wonderful time in chicago and the apartment was perfect for my stayit's a studio with a very comfortable bed working area and an equipped kitchenCleanliness:
perfect clean and big enough for 2the apartment is very clean and the bed comfortabledespite being small and a bit dated everything was very cleangood clean little studio in a nice part of townthe apartment was clean and provides everything you needHost:
krill was a great hostkyril was a great host and very responsive to our messageshost responded to messages very quickly and check in process was easykirill was really nice and helpful to help us with some logisticskirill was a great host and was attentive to us every step of the way during our stayRead more reviewsLocation:
great location in old townlocation was greatnice location and good pricegreat location by the park close to dining beautiful streets to wander downa good location which is very near to cta red line
10. Relaxing private apartment
This apartment is cozy and elegant with a spacious balcony. It features a comfortable mattress with soft linens for a good night’s sleep, a dining room, and a balcony with access from both living room and bedroom. The property also has a great location- just across the street are restaurants, coffee shops, convenience store and public transportation. A public swimming pool and a gym are also available for guests looking for some recreational activities.
Chicago, Illinois, United States
1.19 km (0.8 mi) from 875 North Michigan Avenue
11. Historic downtown condo
This luxurious condo unit is located in a historic building built in 1901- once the home of the Bush and Gerts Piano Company and the Bush Temple of Music. Its renaissance design and ambiance have been preserved but now created into a beautiful and stunning hotel-style building. It features a grand lobby where guests can relax all day, a coffee shop, and a fitness center for guests to have a quick exercise. A plus for this booking is that guests have access to the rooftop terrace where they can enjoy a few drinks and a barbecue in their grill station.
Chicago, Illinois, United States
777 meters (0.5 ft) from 875 North Michigan Avenue
12. Luxury bedroom located downtown
This is a very elegant and modernly decorated bedroom. It gives priority to comfort and class and is definitely a great value for money. It is located in Central Chicago so guests can conveniently enjoy everything that Chicago has to offer. From the bustling city streets, entertainment, sight-seeing to food adventure in some of the most delicious restaurants, guests will definitely have a wonderful time at the heart of the city. Guests also have access to their pool, fitness center and lounge area.
Chicago, Illinois, United States
837 meters (0.6 ft) from 875 North Michigan Avenue
13. Trendy two-bedroom apartment
This modern and stylish apartment is located at the center of Chicago. It has a minimalist design with wooden floors, white-painted walls, and a toned-down gray sofa and red-colored carpet for an accent. It has large windows for a view outside the city and a fully air-conditioned apartment with a heater for a pleasurable stay. The place is close to the popular restaurants around the city, the Chicago River, and a whole lot of entertainment spots just around the corner.
Chicago, Illinois, United States
790 meters (0.5 ft) from 875 North Michigan Avenue
14. Studio apartment in great location
This cozy apartment is well-maintained and squeaky clean for a pleasurable stay. It can accommodate three guests with one comfortable bed which fits two and one sofa bed which can fit one, perfect for couples or friends. Guests love booking this apartment because of its great location, a walking distance from Michigan Avenue, upscale shopping stores, parks, restaurants and bars, perfect for all kinds of fun for all ages. Guests who are light sleepers might have to bring an ear plug because the apartment surroundings might be noisy at night.
Chicago, Illinois, United States
924 meters (0.6 ft) from 875 North Michigan Avenue
15. Unique studio apartment
This apartment is luxurious and stylish, located in the vibrant city of Chicago. It’s spacious and modernly designed for a smooth and pleasurable stay of guests. This apartment can accommodate four guests who are treated to a great view of the city of Chicago with its full glass window with a balcony. It features a queen-sized bed with comfortable linens, a lovely sofa, a flat-screen TV for some entertainment and a fully equipped kitchen with marble countertops. It is located near restaurants, bars, shopping centers, and landmarks.
Chicago, Illinois, United States
908 meters (0.6 ft) from 875 North Michigan AvenueTop guest reviews
Amenities & Room:
comfortable mattress and pillowsloved the big-screen tvvery comfortable clean modern interior and the wifi was fast and easy to connect tothe studio was cozy and all we needed since we planned on exploring the beautiful city of chicagogreat location wonderful view and very comfortableCleanliness:
the room was perfectly clean with lots of clean towelsthe place was very clean and a good sizevery clean and comfy bed with lots of pillows and spare blankets and whatnotthe place was very clean and very convenient to everything we wanted to do in chicagothe apt is very neat and clean equiped kitchen and comfortableHost:
thanks josie for being so kindRead more reviewsLocation:
great place in a great locationexcellent location very centric and very nearby the train stationgreat place and great locationwonderful time at a wonderful locationoutstanding airbnb great location very cool place
The bustling city of Chicago
There is definitely a list of things to do, places to see and food to eat in the bustling city of Chicago. Tourists will surely have a wonderful time experiencing the rich culture and the vibrant city that it is. These top accommodations will definitely complete the entire experience and will leave the tourists wanting for more in this beautiful city of Chicago.
Frequently asked questions about the best Airbnb vacation rentals in North Side, Chicago
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