
Apartment holiday rentals in South Loop, Chicago
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Top-rated apartment rentals in South Loop, Chicago
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Popular amenities for South Loop, Chicago apartment rentals
Weekly apartment rentals

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

Chicago Gem, Art Gallery w/ Parking
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!

Modern 2B2B with Parkings
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.

The Landing @ South Loop
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!!!!

Sonder Market Hall | King Studio Apartment
great place to stay, really nice comfortable bed and full equipped kitchen

BOHEMIAN LODGE #4 ( clean & affordable travel)
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.

Chicago 1BR Condo w Free Gated Parking & WiFi
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!

Vintage Apt in West Loop 3-flat
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

Spacious 1-bedroom South Loop Loft I Sleep 5
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!

McCormick 2B/2Ba w opt parking for up to 6 guests
Malian is s great host and very responsive. When we needed something he was able to get it to us quickly.

Cozy & FREE parking 2BR apt in Chicago Chinatown!
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!

Loft-Inspired Retreat | Stylish Stay Near Downtown
Great location. Near grocery store, great restaurants in the heart of Pilsen, and the green/pink line to get to downtown Chicago.

Explore Lincoln Park from a Polished Apartment
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!

Kasa | Nearby Millennium Park | River North
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!)

Chicago Luxury Long Term 30+
great location. very responsive. Definitely would book again

Comfy Chinatown Chicago - Central & Close to Train
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

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

Spacious Beautiful Condo
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.

Skyline Oasis: City & Lake Views
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!!

Rooftop HotTub As Seen On "Married At First Sight"
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!!

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
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.

Large Studio Apartment with no cleaning fee
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!

Lincoln Park Haven: Balcony, Walk to Whole Foods
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.

Chicago/Beverly/Evergreen Park Home
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center