Top 11 Airbnb Vacation Rentals In Chicago, USA - Updated 2023

airbnb Chicago
| 5 min read

Welcome to Chicago, a city full of history and home to excellent food. Museum buffs will love the Art Institute of Chicago, Museum of Science and Industry and The Field Museum among others. Alternatively, spend a day at Millennium Park and Cloud Gate and ignite your senses with various sights, smells, sounds and tastes. Moreover, Chicago’s music, film, theater and comedy, have shaped much of American culture into what it is today. Come take a trip to the Windy City and see what it has to offer! Here are some great Airbnbs for both couples and solo travellers alike:

1. Modern studio apartment near Millennium Park (from USD 209)

If you’re looking for a comfortable home base for your Chicago travels, check out this studio apartment. This rental is situated right in the middle of where the action is as parks, convention centers, clubs, restaurants, shops, theaters and more, are just within walking distance.

The studio apartment features large windows that not only allow plenty of natural light in, they also provide stunning views of the city. It is furnished with a cozy queen bed with a memory foam mattress that ensures an invigorating sleep. Guests can also prepare meals in the modern kitchen. Heating, air-conditioning, Wi-Fi, flat-screen TV with Cable, Netflix, and YouTube, and a dedicated workspace add convenience to the relaxing place.

Chicago, Illinois, United States
178 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
great apartment with awesome view
i had to work throughout the days i was there and the wifi was strong and reliable
very clean upon arrival as well
clean spacious and comfortable
the place was spacious for a studio and was immaculately clean
super clean and convenient to pretty much everything will definitely stay again my next time in chicago
pristine clean space and affable service staff
matthew is really helpful
matthew was a great host and quickly answered any and all questions i had
matthew was very helpful through the check-in process and with any additional questions i had
clear directions communicative host and great location
matthew is an amazing host great communication
very nice location & studio style
it was also in a fantastic location being close to the riverwalk michigan ave
absolutely excellent location for great restaurants and main sightseeing of chicago
amazing location & great hospitality
and other great places near the north end of the loop
Read more reviews

2. Cozy and Convenient Bedroom

Cozy and Convenient Bedroom
Source: Airbnb

49 USD/night, 15 USD/night per person after the first guest (accommodates 2)

Enjoy a night’s rest in this comfortable and spacious bedroom complete with a queen-size bed and full-size closet. Close to downtown and Chinatown, the townhouse is near several museums and convention at McCormick Place. Stay among an extremely diverse and vibrant community in South Loop. Alternatively, take a walk and visit Art Institutes and Lake Michigan. If you need to travel to other attractions in Chicago, take advantage of the 24-hour buses near the townhouse. Do note that the kitchen is not available to guests.

3. Warm Artsy Comfort

Warm Artsy Comfort
Source: Airbnb

114 USD/night, 30 USD/night per person after the first guest (accommodates 2)

As its name suggests, this apartment is inviting, comfortable and tastefully decorated. Relax in the privacy of your very own bedroom or have a good read from your host’s extensive book collection in the living room. With its high ceilings and large windows, this bright apartment is close to Art Institute and Millennium Park. Moreover, you will be a 5-minute walk from all bus and subway routes. Your hosts, whom you’ll be sharing the apartment with, look forward to answering any of your questions and sharing with you excellent eateries.

4. Downtown Chicago Town Home

Downtown Chicago Town Home
Source: Airbnb

110 USD/night for 2 guests

Ideal for business travellers, this Downtown Chicago Town Home is located just minutes away from train lines and buses. However, many attractions are located within a walkable distance, including several museums, Grant Park and Showcase Jazz. While you’ll have access to the kitchen, there are plenty of highly rated restaurants around the area. You will enjoy a private all-white bedroom and bathroom, and share the home with your friendly host who will give you insights on Chicago’s best.

5. Lincoln Park Bedroom

Lincoln Park Bedroom
Source: Airbnb

63 USD/night for 2 guests

Stay in a snug bedroom in a homely townhouse located between Lincoln Park and Lakeview. Near several wonderful restaurants, fashionable shops and even a yoga studio, this townhouse is well located with bus stations and metro stations nearby. You will definitely enjoy the company of your friendly host family who owns a small dog and cat. This Lincoln Park Bedroom is an excellent place for couples seeking to explore the city.

6. West Loop Art Gallery Loft

West Loop Art Gallery Loft
Source: Airbnb

88 USD/night for 2 guests (excludes 20 USD cleaning fee)

Come home to this comfortable and colourful apartment after a long day of viewing nearby art galleries, dining in exquisite neighbourhood restaurants and exploring Chicago’s best attractions. Moreover, the blue subway line is virtually around the corner while many supermarkets are in close proximity. Your warm and helpful host will welcome you with open arms into her home.

7. Cozy Apartment in Trendy Neighbourhood

Cozy Apartment in Trendy Neighbourhood
Source: Airbnb

50 USD/night for 2 guests (excludes 5 USD cleaning fee)

Formerly a recording studio, this apartment has been transformed into a quirky and interesting living space. Your hosts, whom you will be sharing the apartment with, are a lovely and accommodating couple who are always up for a chat. Ideal for couples and backpackers who wish to explore Chicago, this red-bricked apartment is just minutes away from several restaurants, bus stops and subway stations.

8. Bedroom in Historic Chicago Loft

Bedroom in Historic Chicago Loft
Source: Airbnb

85 USD/night for 2 guests

Share this enormous historic loft with your friendly and amiable host, but have the guest bedroom and bathroom all to yourself. You’ll have an excellent view of South Loop, and have an array of restaurants to choose from, from sports bars to classic Chicago steakhouses. A 10-minute walk northwards will bring you to Downtown, while a 15-minute walk south will lead you to McCormick Place. Your outgoing host loves showing off his city and getting to know new people.

9. Penthouse on Michigan Avenue

Penthouse on Michigan Avenue
Source: Airbnb

This gorgeous penthouse offers access to the living area complete with a flat-screen TV and a kitchen fully equipped with everything you need. Moreover, check out the breathtaking view at the flourishing patio overlooking Michigan Avenue. You can even dine with your hosts and get to know them better! Alternatively, head down to the excellent range of restaurants in the neighbourhood. You’ll also be just a few blocks from great attractions such as Grant Park and the Field Museum.

107 reviews  
Private room 1 Bed 2 Guests

10. Posh Flat

Posh Flat
Source: Airbnb

This cozy bedroom for one is designed to be similar to sleeping in the berth of a ship or a train sleeper car. The flat itself is an interesting collection of furniture from the 1940s to the 1970s and has been decorated lovingly with 20th-century pottery and artworks. Located in close proximity to Downtown Chicago, this excellent apartment is close to breathtaking lakes, thrilling nightlife and convenient public transportation. Moreover, you’ll be sharing the apartment with your friendly and outgoing hosts who are more than happy to help you with anything.

Chicago, Illinois, United States
330 reviews  
Private room in apartment 1 Bed 1 Bedroom 1 Bathroom

11. Norwood Park Bedroom

Norwood Park Bedroom
Source: Airbnb

If you’re looking for a homestay experience further away from the city, this Norwood Park Bedroom is ideal for you. This brick house consists of a living room, kitchen, guest bedroom and bathroom. Moreover, Norwood is a very safe and scenic area known for its abundance of greenery. Your amazing host will do everything in her power to make your stay as comfortable as possible. Cat lovers will be happy to know she owns two adorable kittens.

Chicago, Illinois, United States
179 reviews  
Private room in house 1 Bed 1 Bedroom 1 Bathroom

Check out Chicago!

You’ll never have a dull moment in the city. Come experience the intriguing museums, rich culture and exhilarating nightlife for yourself! Additionally, enjoy the warm hospitality of the locals in Chicago with these Airbnb accommodations. So what are you waiting for? Book your accommodation now!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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