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! It is home to beautiful lakes, shopping malls, theme parks, and delicious pizza places. 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! Read on for the best Airbnb vacation rentals near South 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 April 08, 2024.
1. Modern condo near the lakefront (from USD 100)
This third-floor condo unit is accessible by a flight of stairs. It comes with its own entrance, providing guests with privacy during their stay. Other amenities include cooking basics in the kitchen, a TV in the living area, and Wi-Fi throughout the place. Guests are also provided with access to the shared laundry room that features a washer and a dryer.
When not relaxing in the shared garden space of the property, guests can do some sightseeing starting with the lakefront area just four blocks away from the property.
Top guest reviews
Amenities & Room:
plenty of space for relaxing--and nicely furnished--big comfy bed and well stocked kitchengreat stay at chiaka’s place unique spotless clean comfortable and all needed amenities includedCleanliness:
the bed was super comfortable and everything was so clean we loved the placethe unit is clean comfortable with lots of amenitiesHost:
she was a very responsive hostchiaka was a wonderful host she is so sweet and checked on us to make sure everything was satisfactorythe host is friendly and very communicative before check in and throughout my staychiaka is an awesome host that i'll strive to be like if ever becoming a host myselfchiaka was a very great host and she communicated with me oftenRead more reviewsLocation:
we appreciated the location in a quiet neighhood and an easy walk to lake shorewe loved staying at chiaka’s place
2. Well-located retreat with private parking (from USD 47)
With modern comforts and a great location, this vacation rental provides an ideal home base for your adventures near South Side. Some notable places within a 5-minute drive of the rental include Hyde Park, the Museum of Science & Industry, and Jackson Park Golf Course. Downtown Chicago, which features a plethora of shops and restaurants, is only a 15-minute drive away. 2 private parking spots are also available on-site, making it convenient for you to bring a car and reach more points of interest.
Inside the cozy studio, amenities such as central heating, a high-definition TV, and a full kitchen are available. A free self-serve breakfast is also provided so you can jumpstart your day and enjoy a wonderful time near South Side.
Top guest reviews
Amenities & Room:
the unit had nice furniture equipped with a tv and roku with surround sound stereo and free wifithere is one real bed but the couch turns into a bed and works just as wellwe appreciated that it came stocked with a breakfast bar as well as some bathroom toiletriesconstantly kept common areas clean and provided spring water cereal breakfast snacks masks gloves and hand sanitizerCleanliness:
the place is so cleanHost:
great accommodation from the hostandy was an amazing host he delivery next level costumer service during my trip back home to chicagoandy is a great hostandy is probably the best host i’ve had on this appandy is a wonderful hostRead more reviewsLocation:
love place in a great locationi love this place and looking forward to come back again in futuremy stay in chicago was made so much better for the ease and comfort of staying at andy's place
3. Bright private studio in Bridgeport (from USD 53)
This cozy apartment near South Side, Chicago, 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. 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. You are also free to use the yard though note that 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 could even recommend some places you can visit on your stay.
Top guest reviews
Amenities & Room:
great lighting heating and wifi and great restaurants nearbyand the heater is such nice touchit was private well kept and comfortableCleanliness:
very clean & warmsmall clean place to stayrob’s place was very clean quiet and spacioushis studio was very clean and homey feelingthe space was cozy and cleanHost:
great place great hospitality awesome host thanks robyou are a kind and amazing hostrob was a fantastic host and communicated our check in instructions very clearlygreat host and great place to stayrob's a great host who's helpful and responsive though also really respects your privacy and gives you spaceRead more reviewsLocation:
location is pretty goodgreat location with a variety of restaurants nearbyor has a great location in a charming neighborhood of chicagoit's easy to get to the bus to get downtowngreat location responsiveness and accommodations
4. Luxurious penthouse in a central location
Make your next trip to Chicago a lot more luxurious by staying in this penthouse suite. This apartment for rent near South Side 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.
Chicago, Illinois, United States
11.98 km (7.5 mi) from Museum of Science and Industry, ChicagoSuperhost
Accommodates: 7
Top guest reviews
Amenities & Room:
very comfortable and nice furniture and fixturesthe beds are so comfortable and the view is the most amazing view i’ve even seen in chicagoview from apartment is amazingstunning views hip location super clean and comfortable space plethora of nice building amenitiesyou do not need reservations to use the pool and it was great lots of lounge chairsCleanliness:
great penthouse very clean and equipments are fully preparedthe unit is beautiful and clean with wonderful viewsextremely clean giving the feeling of home away from homeHost:
the host was really communicative and welcomingthe host was very responsive with communicationsthat along with wonderful and attentive hosts made this just a delightful stayexceptional host highly recommend cloud9easy checkin and very accommodating with swift communicationRead more reviewsLocation:
amazing location and flawless experienceamazing property perfect locationgreat space in a fantastic locationloved how close it was to all the michelin star restaurantsgreat location and space for our girls trip
5. Beautifully restored apartment near downtown Chicago (from USD 32)
Just 15 minutes south of downtown Chicago is where you’ll find this beautifully restored 1,000 sq ft. (92.9 sqm) rental! It is a two-bedroom apartment near South Side that 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.
Top guest reviews
Amenities & Room:
great wifi tv and small snacks from the hostthe rooms were sufficient and the kitchen allowed us to cook some meals easilyyou have a 3 room apartment with a nice equpitment kitchen for yourslefCleanliness:
so clean and comfyeverything was clean and there were plenty of towels soaps shampoos dishes etcit is really clean and really quietvery clean and very prepared for youthe place was clean and had everything that we neededHost:
the hosts are awesomethe host was very attentive and responsivethe host is very friendly and welcominga very thoughtful hostthanks to the hostsRead more reviewsLocation:
the location is not the only problemthe community seemed close knit and proud and we really enjoyed our timeoverall this place was super ideal for our stayexcellent location this is the lowest price you'll find for this valuethe place itself is cute and very spacious
6. Cozy one-bedroom cottage (from USD 118)
This cozy and welcoming one-bedroom Airbnb is nestled in Bronzeville, Chicago . 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.
Top guest reviews
Amenities & Room:
the outdoor space is charming and inviting while the units are comfortably spacious and cozyit was a cute space and had amenities like cookware iron laundry etc that were very convenientbeautiful place with great amenities comfy bed-super cozy with everything you needsuch a cozy comfortable and modern cottage in a quiet bronzeville neighborhoodmelissa's apartment is attractive well equipped and comfortableCleanliness:
a very clean and cozy placeexceptionally clean and very stylishbeautiful space and very cleanvery clean and a nice quiet neighborhoodit was spotlessly clean quiet and privateHost:
she was very helpful and quick with responsesthe hosts are great peoplehosts are very friendly and hospitablehost are super nice and hospitablemelissa's was a great hostRead more reviewsLocation:
this was such a cute place to stay at and really close to downtowngreat location for exploring the windy citywonderful park right across the street from spacemelissa's place was really ideal for uswill definitely stay again and/or suggest to anyone needing a place in chicago
7. Cozy quarters steps away from the lake
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!
Chicago, Illinois, United States
3.72 km (2.4 mi) from Museum of Science and Industry, ChicagoAccommodates: 2
Top guest reviews
Amenities & Room:
kay’s place was great the perfect size and great amenities for a comfortable stayCleanliness:
super clean and comfortablevery cleanthe condo was very clean and cozyextremely clean and very stylishvery nice place clean and welcomingHost:
the host is responsive and friendlykay was a great host who responded quicklykay was an amazing hostkay was very responsive to any questions we hadkay is an amazing host who was quick to respond and answer any questions we hadRead more reviewsLocation:
the location was greatgood neighborhood very close to lakekay’s place was in a great location super close to downtown and not too far from the airportnice location a little bit out of the city but close enough to easily get to downtownalso super close to downtown chicago
8. 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!
Chicago, Illinois, United States
3.76 km (2.4 mi) from Museum of Science and Industry, ChicagoAccommodates: 3
Top guest reviews
Amenities & Room:
loved the touch of oj and breakfast foodsspacious and very comfortable with good temperature control(it was snowing outside) in a quiet neighbourhoodangela was easily accessible the apartment was clean and had sufficient air conditioningthere is a portable a/c unit available which is nice if you’re staying during the summerCleanliness:
very clean and comfortablea clean and warm atmosphere for a weekend staythe apartment was clean and spaciousvery clean and area felt safe around the apartmentquiet safe clean and comfortableHost:
the host was very thoughtfulangela was a great hostangela is a great hostangela is a great hostgreat place super nice host answers quicklyRead more reviewsLocation:
excellent location and very close to downtowncharming house and locationthe location was absolutely perfect and so close to the waterthe location was amazing right in the heart of the citythe location of this place is excellent
9. 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.
Chicago, Illinois, United States
9.4 km (5.9 mi) from Museum of Science and Industry, ChicagoAccommodates: 10
Top guest reviews
Amenities & Room:
wi-fi is pretty slow and spottyif the wifi/parking were remedied i’d definitely stay againapartment was clean and the air conditioner made it niceeverything needs a good scrubbing including the floors and the bathroomsounds like they're in the room with you and they aren't quiet peopleCleanliness:
the place was clean and quietthe bathroom felt cleansuper great place very cleaneverything was clean the space is small but for two people it was just finevery pleased with the cleanlinessHost:
host was very responsivehost was friendly and responded fairly quick to any questions i hadfruit and drinks were thoughtful touches provided by the hostleon was a great host; very communicative and accommodating of my travel schedulea great place to stay & quick responses from the hostRead more reviewsLocation:
the location of the apartment was amazing in a great location 15 mins from downtown chicagonice place in a fun locationnice apartment in a great locationwalking distance to the best carnitas corner store liquor store etcgreat space and great location
10. 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.
Chicago, Illinois, United States
8.32 km (5.2 mi) from Museum of Science and Industry, ChicagoTop guest reviews
Amenities & Room:
bed was incredibly comfortable and entire space was super cool / with a vintagey feelthe space is lovely and comfortablethe house was clean and comfortable with a back patio off the main roadeclectic furniture clean and comfortableeverything about our stay was comfortableCleanliness:
very clean and neatly decoratedclean quite and spacious apartmentsuper clean artistic and comfortableit was very clean and well furnishedeverything was immaculately clean and plenty of towels etc were providedHost:
host was respectful and quick with responsesvery helpful host and understandingowner was super helpful with suggestionsgenevieve was a great hostlovely place with a great hostRead more reviewsLocation:
great location with easy access to public transportationlocation is great quiet but close enough to downtown chicagogood layout in a decent locationeasy walk to the orange line to downtown chicagothis is a great location in an alternative neighborhood in the city
11. 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.
Chicago, Illinois, United States
8.12 km (5.1 mi) from Museum of Science and Industry, ChicagoTop guest reviews
Amenities & Room:
the couch and bed were extremely comfortablehome was beautiful wifi would not work but other than that had a beautiful time in this homeCleanliness:
apartment matches the pictures; very clean and modernthe space was very clean toothe flat itself was really clean and greatthe place was very clean and very beautifulgreat place very clean and lots of roomHost:
responses were quick and helpfulthe accommodations were great and the host was very responsivegreat host and perfect apartmentreserve rentals was very responsive and getting into the apartment was very convenientRead more reviewsLocation:
great location if you're attending a conferencegreat value and unit was as advertised in a central quiet area close to bus and l stopsthis is a great location if you are attending a conference at mccormick placeclean comfortable space walking distance (20 min) to soldier fieldreally nice place in great location thanks for a great stay
12. 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!
Chicago, Illinois, United States
7.79 km (4.9 mi) from Museum of Science and Industry, ChicagoTop guest reviews
Amenities & Room:
had some issues with the wifi but didn’t spend too much time indoors so it was okaybed was super comfortablebottle of wine on the table was a nice touchCleanliness:
the place was clean and stylishclean 1bedroom apartment with everything you needvery clean and modern apartment in a historic downtown buildingvery stylish and cleanthe place was very neat and cleanHost:
the host is super nice and she always was willing to helpthe check in was so easy and the hosts were very responsivety was very accommodatinggreat location if you’re attending a conference the hosts were very communicative and everything went smoothlyRead more reviewsLocation:
great location very safegood location and very nice building close to convention centerawesome location and a great neat loftthis is a great location with plenty of transportation options close bywell done space easy location
13. 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!
Chicago, Illinois, United States
8.36 km (5.2 mi) from Museum of Science and Industry, Chicago
14. 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!.
Chicago, Illinois, United States
1.5 km (1.0 mi) from Museum of Science and Industry, Chicago
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!
Frequently asked questions about Airbnb vacation rentals near South Side, Chicago
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