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 The Loop
4.88 out of 5 average rating, 34 reviews

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

AdrianRating, 5 stars2 weeks ago
Location, location, location!! Everything was within a 10-minute walk, with lots of restaurants, coffee spots and stores nearby. The place itself was amazing! Very clean and a very responsive host. Highly recommend!
Superhost
Private room in Pilsen Historic District
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!
Flat in Near South Side
4.65 out of 5 average rating, 17 reviews

Modern 2B2B with Parkings

WilliamRating, 5 stars4 days 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.
Flat in The Loop
4.66 out of 5 average rating, 89 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 West Loop
4.72 out of 5 average rating, 324 reviews

Sonder Market Hall | King Studio Apartment

Fernando & SanneRating, 5 stars4 weeks ago
great place to stay, really nice comfortable bed and full equipped kitchen
Superhost
Private room in Pilsen Historic District
4.82 out of 5 average rating, 201 reviews

BOHEMIAN LODGE #4 ( clean & affordable travel)

JeffRating, 5 stars1 day 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.
Flat in Near West Side
5 out of 5 average rating, 3 reviews

Chicago 1BR Condo w Free Gated Parking & WiFi

MatielRating, 5 stars1 week ago
Great stay — very clean space with unique decor that really suited my style. The location was perfect, close to downtown Chicago and the medical district. The host was very responsive and easy to communicate with. Having a parking spot included was a huge plus. Would definitely stay again!
Flat in West Loop
5 out of 5 average rating, 4 reviews

Vintage Apt in West Loop 3-flat

AntonRating, 5 stars5 days 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
Flat in The Loop
4.93 out of 5 average rating, 174 reviews

Spacious 1-bedroom South Loop Loft I Sleep 5

DaisyRating, 5 stars1 week 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!
Superhost
Flat in Near South Side
4.84 out of 5 average rating, 118 reviews

McCormick 2B/2Ba w opt parking for up to 6 guests

ConradRating, 5 stars1 month ago
Malian is s great host and very responsive. When we needed something he was able to get it to us quickly.
Flat in Chinatown
4.75 out of 5 average rating, 51 reviews

Cozy & FREE parking 2BR apt in Chicago Chinatown!

AshleyRating, 5 stars3 weeks ago
This location was perfect for a short stay for an event at Soldier Field! While the train was nearby, it wasn't as loud as we expected; it didn't interrupt our sleep. The neighborhood is very cool and easy to navigate. My husband and I walked back from Soldier Field after midnight and felt very safe. The unit was nice also; the free parking space was awesome and you are super close to the Red Line if you want to take public transit!
Guest favourite
Flat in Chicago
4.94 out of 5 average rating, 18 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

ZacharyRating, 5 stars1 week ago
Great location. Near grocery store, great restaurants in the heart of Pilsen, and the green/pink line to get to downtown Chicago.
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 River North
4.81 out of 5 average rating, 275 reviews

Kasa | Nearby Millennium Park | River North

NicoleRating, 5 stars1 week ago
Everything about this stay was perfect for a chicago getaway. Easy check in! Great price! Great view! All you need for 2 people - had everything equipped for cooking. Loved the breakfast restaurant and coffee shop downstairs. A dog park is only 1 block away - will definitely choose to stay here again! (Also great amenities!)
Guest favourite
Flat in West Loop
5 out of 5 average rating, 13 reviews

Chicago Luxury Long Term 30+

BrianRating, 5 stars2 weeks ago
great location. very responsive. Definitely would book again
Superhost
Flat in Chinatown
4.84 out of 5 average rating, 80 reviews

Comfy Chinatown Chicago - Central & Close to Train

ClareRating, 5 stars2 weeks ago
We really enjoyed our stay at this apartment. I stayed here with my sister and my parents, and the four of us were very comfortable here. We made breakfast one morning and had everything we needed. The Red Line L is literally around the corner and a 10-minute ride for $2.50 will spit you out downtown. We were also delighted to discover multiple bakeries and coffee shops within a 5-minute walk. The neighborhood overall felt very safe and walkable. We would definitely stay again!

Apartment rentals with a hot tub

Superhost
Flat in Logan Square
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
Flat in West Rogers Park
4.84 out of 5 average rating, 77 reviews

Spacious Beautiful Condo

KristinRating, 5 stars1 week 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 West Loop
4.96 out of 5 average rating, 25 reviews

Skyline Oasis: City & Lake Views

NatashaRating, 5 stars3 months ago
Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!
Superhost
Flat in Chicago
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!!
Superhost
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars2 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 Chicago
4.87 out of 5 average rating, 15 reviews

Large Studio Apartment with no cleaning fee

ErikaRating, 5 stars3 weeks ago
We had a good stay and David communicated very well with help that was needed. Good place to stay with anyone traveling with a small child. Thank you!
Superhost
Flat in Near North Side
4.92 out of 5 average rating, 37 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

HoustonRating, 5 stars1 month ago
We had a great stay at this apartment in Lincoln Park. The view was excellent, and the building amenities were a nice bonus. The location was convenient too--Whole Foods was right across the street, with other shops like REI nearby. It was easy to get downtown and explore other parts of Lincoln Park. We were traveling with a toddler and a newborn, and the host helped by providing a pack 'n play. Communication was clear and timely. Overall, a smooth experience.
Superhost
Flat in Chicago
4.79 out of 5 average rating, 19 reviews

Chicago/Beverly/Evergreen Park Home

CarinaRating, 5 stars2 days 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.

Quick stats about flat rentals in South Loop, Chicago

  • Total rentals

    360 properties

  • Nightly prices starting at

    ₹3,418 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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