15 Best Airbnb Vacation Rentals In North Side, Chicago - Updated 2024

Charisse
Charisse 
Updated
| 6 min read

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.

Stayed at this property?
Chicago, Illinois, United States
5.59 km (3.5 mi) from 875 North Michigan Avenue
181 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the video describing how to enter the apartment complex was very helpful
had some trouble with wifi but hosts were very responsive in getting us on a connecting network
the beds were extremely comfortable
it got pretty chilly in the city but the apartment was very well heated
Cleanliness:
but the place is clean with real chicago charm and well tended to
their place was very clean
a very cozy and clean stay it was easy to find and communication was received well
clean comfortable & had what we needed for our stay
home was very clean and comfortable
Host:
the host was amazing and attentive
hosts are very responsive in communicating and left simple instructions
the owners were very responsive and attentive before during and after the stay
vincent and sofia were responsive to all our questions
vincent & sofia we’re very friendly and have clear instructions on how to get in & get out
Location:
the location was good
we loved the location
great location comfortable beds
apartment location was just perfect - close to restaurants shops & public transportation
great apartment in a great location
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
6.1 km (3.8 mi) from 875 North Michigan Avenue
52 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
excellent stay at jaden’s apartment
Cleanliness:
lakeview is a great neighborhood and jaden’s clean welcoming place was perfect for a long weekend
Host:
he was friendly giving us tips and really responsive
jaden was a great host
all instructions before arrival were easy to follow and he was extremely responsive
very responsive before during and after the stay
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
719 meters (0.5 ft) from 875 North Michigan Avenue
211 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the apartment was stocked with amenities super clean and so cute
the apartment was so beautiful and felt comfortable it was stocked full of essentials for us to use
we had a wonderful stay at tatiana & roupen’s beautiful apartment
i can't say enough good things about this place and was so comfortable for a party of 4
Cleanliness:
it’s clean and fashionable
we found the place extremely clean and organized
this apartment was gorgeous and spotless
beautifully decorated with great amenities extremely clean and excellent communication with hosts
spotless clean and tatiana is amazing — and great location thank you tatiana
Host:
the hosts are also very friendly
our hosts tatiana & roupen were the best
they were helpful when one part of our party had a problem with the keys
hosts checked in to make sure we were happy and even offered early check-in without us asking
they are wonderful hosts
Location:
apartment was cute and great location
a lot of food options near by and great location
this is the cutest apartment in the best location close to everything
the location was perfect half a block off of magnificent mile
it’s in the middle of chicago so perfect if this is the location you need
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
897 meters (0.6 ft) from 875 North Michigan Avenue
143 reviews   Wifi Available
ENTIRE CONDO 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Cleanliness:
warm and wonderful and very clean apartment
it was very clean and check in was easy
it was very clean and easy access in and out
clean spacious and great location
sparkling clean with several thoughtful touches it is the perfect chicago retreat
Host:
rebecca was a wonderful host
rebecca is a great host responsive and super helpful
she was extremely responsive and helped my friends and me sort out a unique situation
she could not have been any more responsive to our needs and was very pleasant to deal with
great host great location
Location:
a cute place in a great location in river north
location was great too
the location was absolutely perfect and very central
the location was terrific with easy access to restaurants and stores like cvs
amazing place in a awesome location
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
270 meters (0.2 ft) from 875 North Michigan Avenue
163 reviews   Superhost Wifi Available
ENTIRE CONDO 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the view from the living room is stunning
the view from the living room and bedrooms are absolutely stunning
the rooms are nice and some amenities are provided; hand towels bath towels etc
the place is spacious clean cozy and loved the view of the lake
two nice and cozy rooms to accommodate you for a nice nights sleep
Cleanliness:
well worth it clean comfortable beds and pillows
super easy check in and the apartment was very clean and spacious
the property is beautiful and very clean
this place is outstanding checking-in was a breeze it’s clean and comfortable
the place was easy to find easy to access and wonderfully clean
Host:
thank you for being such wonderful hosts :)
hosts are very responsive
wonderful hosts and even better city
they were very informative made me feel really comfortable
really nice and even a better host
Location:
the location was great
walking distance to all sorts of restaurants and magnificent mile
all of my favorite downtown chicago places are walking distance
great location exactly like the pictures
great location to walk around shop and see the city
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
1.09 km (0.7 mi) from 875 North Michigan Avenue
33 reviews   Wifi Available
Room in serviced apartment 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
really cool room and the cafe has great coffee and donuts
Cleanliness:
place was clean and new
clean rooms and facility in general
very nice clean place for a short stay
the room was very clean
also the rooms are super clean and comfortable to stay and chill
Host:
staff is very friendly and accommodating
the staff here are very nice and welcoming
Location:
great location near l
in a good location
great place in good location
this place has a very interesting style that stays true to the fieldhouse theme
it was a great and unique place to stay
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
14.15 km (8.8 mi) from 875 North Michigan Avenue
252 reviews   Wifi Available
ENTIRE RENTAL UNIT 3 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
you can sleep two easily as it provides one bedroom and one sofa bed
overall great spacious place with a full sized bed and a foldable couch
the place was comfortable and roomy and actually bigger than expected
i learned a word in polish played darts and pool
nice basement apartment with fully equipped kitchen bathroom and bedroom
Cleanliness:
very clean and private
very clean and nice
the space was very clean and comfortable
apartment was clean and cozy
bathroom was clean
Host:
the hosts are very generous and kind
host was very friendly and accommodating
and both hosts were very helpful and informational
the hosts were also very responsive when we had questions or needed extra toilet paper
pros: hosts were responsive and fair
Location:
good location not too far from bus stops
location was pretty good
wish it was closer to public transportation but still a good stay
good location if you are coming in from the airport
great spot great location great deal
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
937 meters (0.6 ft) from 875 North Michigan Avenue
266 reviews  
Entire apartment 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
little bit of a small apt but perfect for 1-2 people for a short stay
great comfortable place to stay
Cleanliness:
very clean quiet building
the place was very clean and very beautiful on the inside
the place is very clean
apartment is clean serviceable; would stay again
it’s clean and in a wonderful location
Host:
the host is great
great host - easy to communicate - quick responses
nice apartment and great host
great communicative and flexible host
host responded quickly and was great on such a short notice
Location:
location is great walking distance to many popular spots
great location for a quick stay
great location would go back
great location with plenty to do within easy walking distance
great location with everything you need
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
968 meters (0.7 ft) from 875 North Michigan Avenue
87 reviews  
Entire apartment 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the room isn't extra special but the area is fantastic
would have been nice with a tv
pretty basic amenities but clean comfortable and easy to check in and out
i had a wonderful time in chicago and the apartment was perfect for my stay
it's a studio with a very comfortable bed working area and an equipped kitchen
Cleanliness:
perfect clean and big enough for 2
the apartment is very clean and the bed comfortable
despite being small and a bit dated everything was very clean
good clean little studio in a nice part of town
the apartment was clean and provides everything you need
Host:
krill was a great host
kyril was a great host and very responsive to our messages
host responded to messages very quickly and check in process was easy
kirill was really nice and helpful to help us with some logistics
kirill was a great host and was attentive to us every step of the way during our stay
Location:
great location in old town
location was great
nice location and good price
great location by the park close to dining beautiful streets to wander down
a good location which is very near to cta red line
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
1.19 km (0.8 mi) from 875 North Michigan Avenue
25 reviews  
Entire apartment 2 Beds 4 Guests 1 Bedroom 1 Bathroom

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.

Stayed at this property?
Chicago, Illinois, United States
777 meters (0.5 ft) from 875 North Michigan Avenue
104 reviews  
Entire apartment 6 Beds 2 Bedrooms 2 Bathrooms

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.

Stayed at this property?
Chicago, Illinois, United States
837 meters (0.6 ft) from 875 North Michigan Avenue
125 reviews  
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

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.

Stayed at this property?
Chicago, Illinois, United States
790 meters (0.5 ft) from 875 North Michigan Avenue
150 reviews  
Entire apartment 2 Beds 2 Bedrooms 2 Bathrooms

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.

Stayed at this property?
Chicago, Illinois, United States
924 meters (0.6 ft) from 875 North Michigan Avenue
45 reviews  
Entire apartment 2 Beds 0 Bedrooms 1 Bathroom

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.

Stayed at this property?
Chicago, Illinois, United States
908 meters (0.6 ft) from 875 North Michigan Avenue
29 reviews  
Entire apartment 2 Beds 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
comfortable mattress and pillows
loved the big-screen tv
very comfortable clean modern interior and the wifi was fast and easy to connect to
the studio was cozy and all we needed since we planned on exploring the beautiful city of chicago
great location wonderful view and very comfortable
Cleanliness:
the room was perfectly clean with lots of clean towels
the place was very clean and a good size
very clean and comfy bed with lots of pillows and spare blankets and whatnot
the place was very clean and very convenient to everything we wanted to do in chicago
the apt is very neat and clean equiped kitchen and comfortable
Host:
thanks josie for being so kind
Location:
great place in a great location
excellent location very centric and very nearby the train station
great place and great location
wonderful time at a wonderful location
outstanding airbnb great location very cool place
Read more reviews

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.

Stayed at this property?

Frequently asked questions about the best Airbnb vacation rentals in North Side, Chicago


Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Charisse, hailing from the Philippines, spent four years living by the beach, where she found profound happiness and developed an appreciation for the simple joys of island life. She learned to...Read more

 Want to contribute as a Local Expert?
Explore Near North Side
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.