Apartment holiday rentals in South Loop, Chicago

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Popular amenities for South Loop, Chicago apartment rentals

Weekly apartment rentals

Guest favourite
Flat in South Loop
4.89 out of 5 average rating, 35 reviews

Spacious w. Pool, gym, free gift. Sleeps 4

FriederikeRating, 5 stars2 weeks ago
Thank you so much. Looking forward to staying at your place again.
Superhost
Private room in Pilsen
4.95 out of 5 average rating, 129 reviews

Chicago Gem, Art Gallery w/ Parking

RachelRating, 5 stars1 week ago
Colby was the host for me and my friend, very flexible with check-in time and had detailed local recommendations and comfortable linens available for us to use. The room itself was a bit small and warm in the summer but it was definitely clean and worth it for the price!
Top guest favourite
Private room in Chinatown
4.91 out of 5 average rating, 329 reviews

Fantastic Guest room in Chinatown! ️

SunnyRating, 5 stars2 weeks ago
Great Airbnb with a great host in the Chinatown part of Chicago. It was perfect for me on a solo trip to the area. The bed can easily accommodate two people. The apartment was beautiful as depicted in the pictures. Do not hesitate to book!
Flat in South Loop
4.66 out of 5 average rating, 91 reviews

The Landing @ South Loop

CerriRating, 5 stars1 month ago
This was the perfect location! Trader Joe’s, Bus, cafe with delicious coffee and tea, and restaurant all at your doorstep! I will definitely choose this accommodation again when in Chicago!!!!
Flat in South Loop
4.69 out of 5 average rating, 132 reviews

Cozy 1BR in South Loop | Convenience in the City

DavidRating, 5 stars3 months ago
Great place to stay! Can get anywhere in the city, its right off the "L". Not far from Michigan Ave, either. Would highly recommend this place to anyone who is traveling to Chicago.
Superhost
Private room in Near North Side
4.78 out of 5 average rating, 162 reviews

City Beat Room Amidst Chicago's Downtown Gems

AkiraRating, 5 stars3 weeks ago
Thank you very much Shammi. I was comfortable and at ease. I was very happy with my stay and I would like to thank you for your hospitality. It is right in front of the entrance to the Red Line Chicago subway station. If you have a big heavy bag, you should try your best to carry it up. However, the main entrance door to the building is self-locking, so you can safely lift them one by one.
Flat in South Loop
4.74 out of 5 average rating, 27 reviews

The Modern Retreat: 1BR|Near City|Free Parking

ChristianRating, 5 stars3 weeks ago
Global Getaways is a great place to stay. I would definitely stay here again! It is in a great neighborhood and in a convenient location for visiting!
Superhost
Private room in Pilsen
4.82 out of 5 average rating, 201 reviews

BOHEMIAN LODGE #4 ( clean & affordable travel)

JeffRating, 5 stars1 week 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.

Private apartment rentals

Guest favourite
Flat 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
Flat in South Loop
4.89 out of 5 average rating, 128 reviews

South Loop 2BR Apt Near Lakefront & McCormick

Rating, 5 stars3 weeks ago
The apartment is bright and clean. Milan is an excellent host!
Superhost
Flat in South Loop
4.9 out of 5 average rating, 52 reviews

Concise Comfortable Warm place free parking 3B/2Ba

JoeRating, 5 stars2 weeks 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.
Flat 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!
Top guest favourite
Flat in Bridgeport
4.98 out of 5 average rating, 53 reviews

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport

MeraRating, 5 stars1 week ago
The space was clean, comfortable and with all the kitchen supplies that I could need. The mattresses are on the soft side, which was nice for my body. The furniture was comfortable in comparison to other places we have stayed. The neighborhood is walkable with lots of great food options. They have good quality supplies to use, which restored my faith in Airbnb a bit. I felt right at home. I would stay again.
Top guest favourite
Flat in Lincoln Park
5 out of 5 average rating, 263 reviews

Explore Lincoln Park from a Polished Apartment

KatieRating, 5 stars1 week ago
You can believe the hype of the great reviews. Beth’s place has everything I want in an Airbnb. The decorations were thoughtful, there’s coffee and a full kitchen and a great shower and so many windows - all with black out blinds for night. Plus, the area is fantastic. I went on great neighborhood runs and it’s a quick straight shot to the lake too. Plus, the bus downtown is on the corner and really easy to navigate. Oh! And she left cookies for me! Thank you thank you, Beth!
Superhost
Flat in Pilsen
4.85 out of 5 average rating, 397 reviews

Cozy Garden Apartment in Heart of Pilsen

LuisRating, 5 stars3 weeks ago
We enjoyed our stay. Very calm area. At times guest up stairs can be loud when walking but no issue at all. Easy in and out and felt right at home. Hope to stay with you again soon.
Guest favourite
Flat in South Loop
4.94 out of 5 average rating, 154 reviews

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

ShellyRating, 5 stars1 week 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!

Apartment rentals with a hot tub

Superhost
Flat 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
Flat 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
Flat 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
Flat in West Loop
4.96 out of 5 average rating, 26 reviews

Skyline Oasis: City & Lake Views

RobertRating, 5 stars4 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
Flat 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
Flat in South Side
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars4 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.
Superhost
Flat in Chicago
4.79 out of 5 average rating, 19 reviews

Chicago/Beverly/Evergreen Park Home

CarinaRating, 5 stars1 week ago
The host is very helpful. The house next door seems to be abandoned; therefore, there is a lot of trash and broken glass on the floor next to this building. The place is very chic and fun. My favorite part was the bath bar and back yard. There are no dishes only cups and coffee mugs no paper towels and no plates. I liked the fact that the host asked questions before approving our reservation. I will definitely reserve again.
Top guest favourite
Flat in Dunning
4.98 out of 5 average rating, 118 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars2 days ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.

Quick stats about flat rentals in South Loop, Chicago

  • Total rentals

    360 properties

  • Nightly prices starting at

    $51 SGD 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

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