12 Best Airbnb Vacation Rentals Near South Side, Chicago - Updated 2022

airbnb chicago south side
Alyssandra Raiza
Alyssandra Raiza 

Chicago is the most populous city in Illinois and the third most populous city in the entire country! It is an internationally renowned city, known for its openness to diversity - in fact, the Windy City was host to an estimated 58 million domestic and international travelers in 2018 alone! Whether you’re traveling with your business colleagues for a conference, visiting a relative in the city, or even just wanting to explore this fascinating city on a solo trip, the accommodation options are as infinite as the things you can do in this city! Check out our picks for some of the best Airbnbs near South Side, Chicago!

1. Comfy studio in Bridgeport (from USD 81)

This studio guesthouse offers a private place for you to simply sit back and rest your tired body. There is a full-sized Murphy bed, couch, and desk that doubles as a chess or checkers table for your comfort and convenience. The kitchenette has a mini-fridge, microwave, and coffee maker for your dining needs. There are also complimentary board games and a small library of books for you to enjoy. The yard is also open for you to rest though the host’s dog may want to come and play with you.

Located in the Bridgeport neighborhood, the home is close to many restaurants, shops, and attractions. The host even recommends some places you can visit.

Private Studio in Bridgeport, Chicago
Chicago, Illinois, United States
272 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 3 Guests 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
great lighting heating and wifi and great restaurants nearby
and the heater is such nice touch
it was private well kept and comfortable
very clean & warm
small clean place to stay
rob’s place was very clean quiet and spacious
his studio was very clean and homey feeling
the space was cozy and clean
great place great hospitality awesome host thanks rob
you are a kind and amazing host
rob was a fantastic host and communicated our check in instructions very clearly
great host and great place to stay
rob's a great host who's helpful and responsive though also really respects your privacy and gives you space
location is pretty good
great location with a variety of restaurants nearby
or has a great location in a charming neighborhood of chicago
it's easy to get to the bus to get downtown
great location responsiveness and accommodations
Read more reviews

2. Luxurious penthouse in a central location (from USD 912)

Make your next trip to Chicago a lot more luxurious by staying in this penthouse suite. This pad can accommodate up to six guests as it features three bedrooms, each equipped with cozy king-size beds. The elegant, modern design is complemented with large floor-to-ceiling windows to give you the best cityscape views. Amenities also include air-conditioning, heating, Wi-Fi, a flat-screen TV, and a modern kitchen.

Guests will also have access to building facilities, which include an outdoor pool and a business center. Its location is perfect for those who want to explore the city as it’s in the middle of everything.

XL Pent House for 6 "The Harper" Full Amenities
Chicago, Illinois, United States
56 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
very comfortable and nice furniture and fixtures
the beds are so comfortable and the view is the most amazing view i’ve even seen in chicago
view from apartment is amazing
stunning views hip location super clean and comfortable space plethora of nice building amenities
you do not need reservations to use the pool and it was great lots of lounge chairs
great penthouse very clean and equipments are fully prepared
the unit is beautiful and clean with wonderful views
extremely clean giving the feeling of home away from home
the host was really communicative and welcoming
the host was very responsive with communications
that along with wonderful and attentive hosts made this just a delightful stay
exceptional host highly recommend cloud9
easy checkin and very accommodating with swift communication
amazing location and flawless experience
amazing property perfect location
great space in a fantastic location
loved how close it was to all the michelin star restaurants
great location and space for our girls trip
Read more reviews

3. Beautifully restored apartment near downtown Chicago (from USD 46)

Just 15 minutes south of downtown Chicago is where you’ll find this beautifully restored 1,000 sq ft. (92.9 sqm) home! With two bedrooms and a private bath, the apartment can comfortably accommodate up to three guests. It also boasts comforts like spacious living and dining rooms, as well as a fully-equipped kitchen, where you can prepare your own meals! Although the apartment was built in the 1930’s the space comes equipped with modern features as Free WiFi, Central air, and a 50" TV with Chromecast. For guests who prefer a quiet and relaxing space, the rear patio and manicured backyard would be perfect. Conveniently, the apartment is also just a five-minute walk to two bus stops and a ten-minute walk from two train lines.

Private, 2BR apt, 6 miles south of Downtwn Chgo
Chicago, Illinois, United States
258 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 3 Guests 2 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
great wifi tv and small snacks from the host
the rooms were sufficient and the kitchen allowed us to cook some meals easily
you have a 3 room apartment with a nice equpitment kitchen for yourslef
so clean and comfy
everything was clean and there were plenty of towels soaps shampoos dishes etc
it is really clean and really quiet
very clean and very prepared for you
the place was clean and had everything that we needed
the hosts are awesome
the host was very attentive and responsive
the host is very friendly and welcoming
a very thoughtful host
thanks to the hosts
the location is not the only problem
the community seemed close knit and proud and we really enjoyed our time
overall this place was super ideal for our stay
excellent location this is the lowest price you'll find for this value
the place itself is cute and very spacious
Read more reviews

4. Cozy one-bedroom cottage (from USD 124)

Nestled in Bronzeville is this cozy and welcoming one-bedroom cottage. The space is located on the second floor, with its own private entrance. In addition to the single bedroom, the cottage also features a private bath - stocked with hygiene essentials - as well as a kitchen, equipped with some basic cooking appliances, including microwave and a Keurig coffee station. Guests can also lounge by the front porch and enjoy the scenery, or head to the back porch and fire up the grill! The cottage is also located about 1.5 mi (2.41 km) from the lakefront and close to a movie theater, as well as a good number of shops and restaurants.

Historic Coach House Cottage
Chicago, Illinois, United States
185 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the outdoor space is charming and inviting while the units are comfortably spacious and cozy
it was a cute space and had amenities like cookware iron laundry etc that were very convenient
beautiful place with great amenities comfy bed-super cozy with everything you need
such a cozy comfortable and modern cottage in a quiet bronzeville neighborhood
melissa's apartment is attractive well equipped and comfortable
a very clean and cozy place
exceptionally clean and very stylish
beautiful space and very clean
very clean and a nice quiet neighborhood
it was spotlessly clean quiet and private
she was very helpful and quick with responses
the hosts are great people
hosts are very friendly and hospitable
host are super nice and hospitable
melissa's was a great host
this was such a cute place to stay at and really close to downtown
great location for exploring the windy city
wonderful park right across the street from space
melissa's place was really ideal for us
will definitely stay again and/or suggest to anyone needing a place in chicago
Read more reviews

5. Cozy quarters steps away from the lake (from USD 65)

This cozy and private one-bedroom garden condo would be perfect for solo travelers or couples. The condo all the comforts of a modern home, including a kitchen, washer and dryer, Wi-Fi access, and cable TV. Guests will also have access to some storage closets and a back patio. Located within a five- to seven-minute walk from downtown, Museum Campus, McCormick Place Convention Center, Hyde Park, University of Chicago campus, 31st Street Harbor, Museum of Science and Industry, and 18 miles (28.9 km) of lakefront beauty, guests will have an ample variety of greats activities to choose from during their stay here!

Cozy quarters steps away from the lakefront
Chicago, Illinois, United States
195 reviews  Wifi Available
Entire rental unit 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
kay’s place was great the perfect size and great amenities for a comfortable stay
super clean and comfortable
very clean
the condo was very clean and cozy
extremely clean and very stylish
very nice place clean and welcoming
the host is responsive and friendly
kay was a great host who responded quickly
kay was an amazing host
kay was very responsive to any questions we had
kay is an amazing host who was quick to respond and answer any questions we had
the location was great
good neighborhood very close to lake
kay’s place was in a great location super close to downtown and not too far from the airport
nice location a little bit out of the city but close enough to easily get to downtown
also super close to downtown chicago
Read more reviews

6. Lakeside apartment near Hyde Park

This one-bedroom lakeside apartment not only boasts gorgeous views of the lake, but also a wide assortment of amenities. Up to three guests can stay comfortably and can enjoy conveniences such as a complimentary breakfast, Wi-Fi connectivity, an indoor fireplace, cable TV, as well as bathroom and bedroom essentials. There is also a fully functional kitchen, equipped with a coffee maker, pots and pans, oil, a dishwasher, microwave, refrigerator, stove, and other basic tools needed for cooking. And with it’s own private entrance/exit, guests will find it easy to get in and out of the apartment - which is ideal, especially since Hyde Park, a number of sports parks, McCormick Place, & downtown are just steps away!

Lake Apt. near Hyde Park &Downtown
Chicago, Illinois, United States
306 reviews Superhost  Wifi Available
Entire serviced apartment 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
loved the touch of oj and breakfast foods
spacious and very comfortable with good temperature control(it was snowing outside) in a quiet neighbourhood
angela was easily accessible the apartment was clean and had sufficient air conditioning
there is a portable a/c unit available which is nice if you’re staying during the summer
very clean and comfortable
a clean and warm atmosphere for a weekend stay
the apartment was clean and spacious
very clean and area felt safe around the apartment
quiet safe clean and comfortable
the host was very thoughtful
angela was a great host
angela is a great host
angela is a great host
great place super nice host answers quickly
excellent location and very close to downtown
charming house and location
the location was absolutely perfect and so close to the water
the location was amazing right in the heart of the city
the location of this place is excellent
Read more reviews

7. Two-bedroom apartment with kitchen

This spacious and bright two-bedroom apartment is the ideal retreat for large groups or families traveling to Chicago! Its 2 bedrooms have enough space to comfortably sleep up to 10 guests at a time, while the 2 baths are kept sparkling clean and stocked with enough hygiene essentials to help everyone keep clean. The apartment also features a kitchen, equipped with a refrigerator, microwave, toaster, coffee maker, and other essentials - perfect for preparing large meals! Guests can also lounge by the living room and enjoy some NetFlix, or chill by the rooftop and enjoy the great view of the city’s skyline. The apartment is also just a stone’s throw away from the University of Illinois, the Grant, and Millennium Parks, as well as a good number of bars and restaurants.

South Loop Cozy 2BdRm parking&WiFi&NetFlix
Chicago, Illinois, United States
514 reviews  Wifi Available
Entire rental unit 2 Beds 10 Guests 2 Bedrooms 1 Bathroom

Accommodates: 10

Top guest reviews
Amenities & Room:
wi-fi is pretty slow and spotty
if the wifi/parking were remedied i’d definitely stay again
apartment was clean and the air conditioner made it nice
everything needs a good scrubbing including the floors and the bathroom
sounds like they're in the room with you and they aren't quiet people
the place was clean and quiet
the bathroom felt clean
super great place very clean
everything was clean the space is small but for two people it was just fine
very pleased with the cleanliness
host was very responsive
host was friendly and responded fairly quick to any questions i had
fruit and drinks were thoughtful touches provided by the host
leon was a great host; very communicative and accommodating of my travel schedule
a great place to stay & quick responses from the host
the location of the apartment was amazing in a great location 15 mins from downtown chicago
nice place in a fun location
nice apartment in a great location
walking distance to the best carnitas corner store liquor store etc
great space and great location
Read more reviews

8. Vintage-style home in Bridgeport

Stay with seven of your loved ones in this charming, vintage-inspired home! With two bedrooms and a private bath, the home can accommodate all of you in comfort. You will appreciate the amenities that come with the place including a fully equipped kitchen, Wi-Fi connectivity, cable TV, heating, and air conditioning. Located in Bridgeport, the home is also not too far from some famous deep-dish pizzerias, as well as some excellent taco joints, specialty Northern Chinese restaurants, and coffee shops.

Kick Back in the Egg Chair at a Vintage-Inspired Oasis
Chicago, Illinois, United States
233 reviews
Entire apartment 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
bed was incredibly comfortable and entire space was super cool / with a vintagey feel
the space is lovely and comfortable
the house was clean and comfortable with a back patio off the main road
eclectic furniture clean and comfortable
everything about our stay was comfortable
very clean and neatly decorated
clean quite and spacious apartment
super clean artistic and comfortable
it was very clean and well furnished
everything was immaculately clean and plenty of towels etc were provided
host was respectful and quick with responses
very helpful host and understanding
owner was super helpful with suggestions
genevieve was a great host
lovely place with a great host
great location with easy access to public transportation
location is great quiet but close enough to downtown chicago
good layout in a decent location
easy walk to the orange line to downtown chicago
this is a great location in an alternative neighborhood in the city
Read more reviews

9. Apartment with modern conveniences

This two-bedroom apartment is a haven for conference attendees & business travelers, as it is conveniently located within five minutes of McCormick Place. The apartment’s two bedrooms each come with its own queen size bed and a sofa bed, while an air mattress is available in the large living area -allowing for up to seven guests to be accommodated comfortably. This apartment successfully melds luxury and city living in a sophisticated, comfortable way The spacious living area, the large balcony with seating, and the fully stocked kitchen make guests feel right at home. Smart TVs with Netflix and DirectTV or the rooftop tranquility pool will help guests relax and unwind after a long hard day.

Domio | McCormick Place | Smart 2BR + Pool and Fitness Center
Chicago, Illinois, United States
43 reviews
Entire serviced apartment 4 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the couch and bed were extremely comfortable
home was beautiful wifi would not work but other than that had a beautiful time in this home
apartment matches the pictures; very clean and modern
the space was very clean too
the flat itself was really clean and great
the place was very clean and very beautiful
great place very clean and lots of room
responses were quick and helpful
the accommodations were great and the host was very responsive
great host and perfect apartment
reserve rentals was very responsive and getting into the apartment was very convenient
great location if you're attending a conference
great value and unit was as advertised in a central quiet area close to bus and l stops
this is a great location if you are attending a conference at mccormick place
clean comfortable space walking distance (20 min) to soldier field
really nice place in great location thanks for a great stay
Read more reviews

10. Posh loft within walking distance of McCormick

This posh loft is the perfect base for business travelers, sports enthusiasts, or even couples on a romantic trip. The unit comes with a good number of amenities, including a laptop-friendly workspace, cable TV, Iron, bedroom and bathroom essentials and air conditioning. Food prep and dining should also be a light experience, with a fully functional kitchen available. For guests who wish to explore the area, McCormick is just around the corner. Nearby is Soldiers Field, the Field Museum, Aquarium, Planetarium, and Lake Shore Drive. There are some great shopping and dining options in the area too!

?POSH Loft Walk to McCormick, Trendy South Loop
Chicago, Illinois, United States
61 reviews
Entire loft 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
had some issues with the wifi but didn’t spend too much time indoors so it was okay
bed was super comfortable
bottle of wine on the table was a nice touch
the place was clean and stylish
clean 1bedroom apartment with everything you need
very clean and modern apartment in a historic downtown building
very stylish and clean
the place was very neat and clean
the host is super nice and she always was willing to help
the check in was so easy and the hosts were very responsive
ty was very accommodating
great location if you’re attending a conference the hosts were very communicative and everything went smoothly
great location very safe
good location and very nice building close to convention center
awesome location and a great neat loft
this is a great location with plenty of transportation options close by
well done space easy location
Read more reviews

11. Studio for two near downtown

If you’re a solo traveler or traveling as a couple, this bright, cozy studio for two in the heart of Bridgeport would bed perfect for you! In addition to its private bedroom and bathroom, the studio also comes with a kitchenette equipped with a coffee maker, some dishes and silverware, a microwave, and a refrigerator. Should you wish to explore the area, you’ll actually be quite close to the White Sox Stadium, UIC, IIT, the Chicago Institute of Art, Chinatown and an abundance of other galleries, coffee shops, parks, and grocery stores!

Bright, Cozy Studio Close to Downtown
Chicago, Illinois, United States
309 reviews
Entire house 1 Bed 1 Bedroom 1 Bathroom

12. Bright and airy apartment for 10

Looking for a large place to accommodate all your loved ones, on your next family trip to Chicago? This bright and airy two-bedroom apartment would be your best bet! The apartment’s two bedrooms can comfortably sleep up to ten guests at a time, and there are two bathrooms available to help everyone freshen up. Each bedroom is not only equipped with a flat-screen TV in for guests’ entertainment - but they also boast large windows and excellent views of the lake! For leisure, guests can enjoy the swimming pool and hot tub in the building. Although there is a restaurant is within the building, the accommodation is located close to a number of shopping centers, and coffee shops - perfect to explore on a family day out!.

5 bd 2 bth Swimming Pool View of lake by McCormick
Chicago, Illinois, United States
97 reviews
Entire apartment 6 Beds 2 Bedrooms 2 Bathrooms

Find a place to call home in the Windy City

Chicago is easily one of the busiest and most diverse cities in the world! In spite of the hustle and bustle of city living, you’ll find the Windy City can actually be quite welcoming. Whether you’re visiting for business or for pleasure, with the help of these excellent Airbnb accommodations, you’re sure to feel right at home on your next trip to Chicago!

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

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