Apartment holiday rentals in South Loop, Chicago

Find and book unique apartments on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for South Loop, Chicago apartment rentals

Weekly apartment rentals

Superhost
Private room in Pilsen
4.95 out of 5 average rating, 128 reviews

Chicago Gem, Art Gallery w/ Parking

NiamhRating, 5 stars1 month ago
There are so many positives about staying here. This is a really unique vibrant and interesting neighbourhood. It is a very short distance from the nearest train station. It is comfortable safe and clean. Donald and his daughter Colby are a perfect hospitality team. They gave a really great run through of the area and are helpful kind and interested. I can see why they are always booked up 😊 Wishing you both well and thank you!
Top Guest favourite
Private room in Chinatown
4.91 out of 5 average rating, 328 reviews

Fantastic Guest room in Chinatown! ️

KrishnaRating, 5 stars3 weeks ago
Dorian’s place was located in the perfect spot, close to public transportation, and many restaurants around in china town. Very clean, well decorated, and comfortable bed.
Apartment in South Loop
4.65 out of 5 average rating, 17 reviews

Modern 2B2B with Parkings

WilliamRating, 5 stars1 week ago
This was a great place to stay. The building is nice and quiet, it was clean, Field and Shedd were easily walkable, and there were good restaurants nearby. There was a Jewel a couple blocks down as well. The host messaged several times to make sure everything was going ok. We would stay at this host's properties again.
Private room in Little Italy
4.78 out of 5 average rating, 79 reviews

Beautiful Private Room 5 min to the City

IngridRating, 5 stars3 weeks ago
Super close to UIC, located in a quiet and safe neighborhood. It’s also not far from downtown Chicago. The apartment has five rooms, with a toilet on the first floor and a full bathroom on the second floor. It can get a bit crowded on weekends, which might make the bathrooms busier, but in my experience, they’ve remained clean despite being shared. That said, cleanliness may vary depending on the tenants. Also, the walls are a bit thin, so noise from the first floor can sometimes be heard upstairs. However, people generally keep quiet after 11 p.m.
Guest favourite
Private room in Chicago
5 out of 5 average rating, 10 reviews

Sweet Pea - Blue Key - Place 3

NeilRating, 5 stars2 weeks ago
Very nice and clean and close to the subway
Superhost
Private room in Pilsen
4.82 out of 5 average rating, 201 reviews

BOHEMIAN LODGE #4 ( clean & affordable travel)

JeffRating, 5 stars5 days ago
This haven is impeccably clean, very comfortable (especially the bed), peaceful and yet convenient to one of the most dynamic neighborhoods in the U.S. Get takeout from Kristoffer’s Cafe (I recommend the chilaquiles) and eat at the chess tables in Reyes Park. Or dine in at La Malinche Coffeehouse. Then walk 18th Street from Halsted at least to Ashland (or onward to the Mexican-American Museum of Art) to see Chicago in its full vivacity. Be sure to visit Open Books across the street from the Bohemian Lodge. You’re also close to UIC, Little Italy, Bridgeport, home of the White Sox, and everything along Halsted Street and it’s frequent 8 bus (Carl Sandberg wrote a poem about the 8). Great place. I’ll stay there whenever I come to The Chi.
Guest favourite
Apartment in South Loop
5 out of 5 average rating, 5 reviews

McCormick Pl 420 friendly 3BR/2BA/sleeps 8/Parking

HaozhengRating, 5 stars1 month ago
The room was clean and well-maintained, with all the essentials provided. The check-in process was smooth and the host was responsive and helpful. Great location with easy access to restaurants and public transport. I had a very pleasant stay and would highly recommend it.
Apartment in West Loop
5 out of 5 average rating, 4 reviews

Vintage Apt in West Loop 3-flat

AntonRating, 5 stars1 week ago
We were absolutely blown away by our accommodation. The apartment is even bigger and more beautiful in real life than we'd imagined from the photos. It is a very spacious apartment, equipped with two massive TVs and a very good air conditioning system. The area it's in is wonderful, with tons of eating options and things to do. We also enjoyed daily walks down to the river and Millennium Park. Mimi, who we communicated with, was very responsive and warm. We will definitely be staying there again when we return!

Private apartment rentals

Guest favourite
Apartment in Little Italy
4.95 out of 5 average rating, 43 reviews

Spacious Studio in Little Italy, Near West Loop

MoriahRating, 5 stars1 week ago
I loved this stay! It was in a great walkable area and not far from downtown Chicago. I would definitely stay again.
Superhost
Apartment in South Loop
4.9 out of 5 average rating, 52 reviews

Concise Comfortable Warm place free parking 3B/2Ba

JoeRating, 5 stars1 week ago
Stayed here during the ASCO conference. About a 5-10 minute Uber ride to conference center and we actually walked home one day. The walk was easy and only took about 20 minutes. The apartment is just as the pictures show. Very nice and clean. 3 of us stayed and there was plenty of room. Only downside was 3 people taking showers quickly drained the hot water. Not unexpected as most apartments don't have a large hot water heater. This wasn't a big issue, just something to be aware of. Wing & Lily were excellnet hosts. Communnicated very well and were understanding when I had an issue getting in the apartment the first time...which was my fault. We will certainly try to stay here next year when we attend the ASCO conference.
Guest favourite
Apartment in South Loop
4.93 out of 5 average rating, 174 reviews

Spacious 1-bedroom South Loop Loft I Sleep 5

DaisyRating, 5 stars2 weeks ago
My husband and I stayed here with our 1.5 year old and it was fantastic! Clean, convenient, and had a pack and play ready for us. I was a bit worried reading prior reviews about noise but it wasn’t bad at all, especially with the white noise machine provided in the bedroom. Our son slept peacefully throughout our stay. Would recommend for sure!
Guest favourite
Apartment in River North
4.87 out of 5 average rating, 47 reviews

50th Floor Mag Mile VIEWS, Balcony, Pool, Gym

JoseRating, 5 stars1 month ago
Beautiful view especially at sunset and night time. And great restaurants nearby.
Apartment in South Loop
4.75 out of 5 average rating, 52 reviews

Cozy & FREE parking 2BR apt in Chicago Chinatown!

PatrickRating, 5 stars2 weeks ago
Nice little spot outside of downtown, can take the subway into the city which makes things easy, Chinatown is a cool place for sure!
Guest favourite
Apartment in South Loop
4.91 out of 5 average rating, 208 reviews

The South Loop Reserve I Sleep 6 I Top Rated

AndrewRating, 5 stars2 days ago
This place is amazing. Very well maintained and furnished. Lots of thought obviously put in to making the stay comfortable. Was a very good size! Lots of room. We were attending conference at McCormick. Very well located. Will visit again.
Guest favourite
Apartment in South Loop
4.94 out of 5 average rating, 154 reviews

Brilliant 2BR/2BA Loft I SuperHost I Sleep 6

ShellyRating, 5 stars6 days ago
It was so nice to have room to spread out with our family. The beds were very comfortable and the place was very clean. The location was fantastic. Very walkable area. We had a great stay!
Superhost
Apartment in South Loop
4.86 out of 5 average rating, 104 reviews

Skyline 2BR in South Loop Chicago Near McCormick

PetroRating, 5 stars1 week ago
As usually, best price/quality comparison, close to heart of downtown. Very light living room, panoramic windows with stunning view. Clean, comfortable apartment. Not first our visit and not last, fore sure. Would definitely recommend this apartment and owner!

Apartment rentals with a hot tub

Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 103 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

BriantRating, 5 stars1 week ago
We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.
Superhost
Apartment in East Rogers Park
4.84 out of 5 average rating, 77 reviews

Spacious Beautiful Condo

KristinRating, 5 stars2 weeks ago
Perfect location for a family to stay that’s close to everything. We did days in the city and a game at Wrigley. Very clean and perfect for our long weekend in Chicago.
Superhost
Apartment in South Loop
5 out of 5 average rating, 34 reviews

Lux Loop Retreat: Amazing Views, Free Parking

JanRating, 5 stars2 days ago
Run, don't walk, to book this location for your Chicago stay. The view of the Chicago skyline is perfect, even better than if you stayed in Downtown itself, sometimes all you see is the wall of another building and no view. The instructions how to get there are very clear, if you're a little intimidated like I was about going to a big city never fear. The instructions are clear, easy to follow, and transit is close by to take you wherever you want to go. Overall great trip, thank you!
Superhost
Apartment in Lake View
4.7 out of 5 average rating, 10 reviews

Minutes to Wrigley Amazing Location - Sleeps 6

MattRating, 5 stars1 month ago
Freddy was an incredibly friendly and responsive host, really went above and beyond to ensure a good trip. The location is perfect, just a few minute walk to everything you could want while still maintaining a quiet residential feel.
Superhost
Apartment in Bridgeport
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!
Guest favourite
Apartment in West Loop
4.96 out of 5 average rating, 26 reviews

Skyline Oasis: City & Lake Views

RobertRating, 5 stars3 weeks ago
Beautiful view of the city. The location is perfect! It is close to the train station and easy for Uber to get in and out of. Lots of restaurants, coffee, gelato, cookies, and donuts within walking distance. Our host was very responsive and quick to answer any questions we had and even provided restaurant suggestions. The balcony view is amazing day or night with the city scape and a view of the lake.
Top Guest favourite
Apartment in River West
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars3 weeks ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
Apartment in South Side
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars2 days ago
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.

Quick stats about apartment rentals in South Loop, Chicago

  • Total rentals

    360 properties

  • Nightly prices starting at

    $66 NZD before taxes and fees

  • Total number of reviews

    15K reviews

  • Family-friendly rentals

    200 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    100 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Loop
  7. Apartment rentals