
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
Thank you so much. Looking forward to staying at your place again.

Chicago Gem, Art Gallery w/ Parking
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!

Fantastic Guest room in Chinatown! ️
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!

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!!!!

Cozy 1BR in South Loop | Convenience in the City
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.

City Beat Room Amidst Chicago's Downtown Gems
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.

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

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.
Private apartment rentals

Spacious Studio in Little Italy, Near West Loop
I loved this stay! It was in a great walkable area and not far from downtown Chicago. I would definitely stay again.

South Loop 2BR Apt Near Lakefront & McCormick
The apartment is bright and clean. Milan is an excellent host!

Concise Comfortable Warm place free parking 3B/2Ba
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.

Cozy & FREE parking 2BR apt in Chicago Chinatown!
Nice little spot outside of downtown, can take the subway into the city which makes things easy, Chinatown is a cool place for sure!

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
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.

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!

Cozy Garden Apartment in Heart of Pilsen
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.

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

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.

Minutes to Wrigley Amazing Location - Sleeps 6
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.

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!!

Skyline Oasis: City & Lake Views
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.

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
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.

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.

Belmont Pleasures - hot tub / arcade gaming room
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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- 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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club