
House vacation rentals in South Loop, Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in South Loop, Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for South Loop, Chicago house rentals
House rentals with a pool

Luxury Condo Downtown Chicago
Paras was an extremely friendly host. He provided a long list of recommendations and made sure we were aware he was only a message or call away.

Munster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Hidden GEM OASIS in Chicagoland
Great place to stay in the Chicago area. Somewhat rural but everything is close. Perfect for our family.

No Cleaning Fee - Whole House With Hot Tub
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.

Luxury Cabin in Lakeview
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!

4Bed GemW/Pool for8 Near ORD/MDW
Very great place, exactly like the photos and description!! House was nice and spacious. On top that great location.

Schaumburg Woodfield Pool House 4bedroom 2.5bath
Everything went perfect for us. We flew in from out of town, and some plans fell through. We asked Mike if it was possible to check in a couple hours early and he was very flexible. We really appreciate you and your home. Thanks for letting us stay.
Weekly house rentals

Family Friendly Duplex/9 min from MDW/Free Parking
Very nice, homey place. We felt right at home! Nice, quiet neighborhood.

Duplex Home RoscoeVillage/Wrigley Free St Parking
Sharleen is such a nice person and host. Her place is really accommodating and comfortable, our team had a great time at her home. Thank you, Sharleen.

Home in Glen Ellyn
It’s a nice place as described. Our stay was pleasant.

Cozy at the Walter
Our go to in the Chicagoland area.... always a pleasure to stay at The Walter

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
Tom was great, friendly, and very helpful, highly recommend

The Avondale Guesthouse
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!

The Spa of Downtown Whiting
Really enjoyed Steven’s place! It was comfortable and spacious, and had everything we needed. Great location that’s not far from Chicago, and lots of shops and restaurants just blocks away. Cute little neighborhood and small town feel. Steven was easy to work with and really responsive. Would love to stay again when we’re in the area!

Wrigleyville Greystone
The place was in a beautiful, quiet neighborhood, and clean and very comfortable for our family of 5 adults. Mark was very accommodating and let us check in two hours early as we arrived in town before we expected to, and it was raining and didn't want to get wet walking around outside. The location was great as we were in town for the NHL Winter Classic, and it was an easy walk to Wrigley Field. Also, lots of great restaurants within walking distance. We were also celebrating Christmas with our family and to our wonderful surprise, there was a tree and many other festive decorations up that made it extra special! We would definitely stay in this location again while in Chicago.
Private house rentals

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.

Warm bungalow in New City
Nice house 🔥

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd
Perfect for our work trip!

Gorgeous and Luxurious 3 BR Home
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.

Grand Victorian Mansion in Austin Area
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.

Warm and comfortable inviting Suburban home !
Great host, nice peaceful home with old-fashioned feel. We even met some friendly neighbors. Rich always responded promptly to questions & was overall kind & accommodating. We enjoyed the area, including many historical homes, local restaurants (DeMar’s😋) and a beautiful event at the iconic Lyric Theater. Thank you!

Quiet cul-de-sac with huge fenced in backyard
Most amazing place to stay 5/5 would recommend.

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
The space was comfortable, very accommodating, and loved the location. Super close walk to California stop for the Green line. Loved that the parking space in the back alley was gated, made us feel a lot better knowing our car wasn’t going to get broken into. WiFi went out on the last night of our stay. However, Joyce was very quick to respond about it and let us know it was an area wide interruption. Overall, great stay and would definitely choose this spot again when in Chicago.
Destinations to explore
- Lighthouse rentals United States
- Earth house rentals United States
- House rentals United States
- Townhouse rentals United States
- Guesthouse rentals United States
- Lake house rentals Chicago
- House rentals Chicago
- Townhouse rentals Chicago
- Tiny house rentals Illinois
- Lake house rentals Illinois
- House rentals Illinois
- Guesthouse rentals Illinois
- Townhouse rentals Illinois
- House rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Townhouse rentals Cook County
- House rentals Cook County
- Condo rentals South Loop
- Pet-friendly rentals South Loop
- Family-friendly rentals South Loop
- Smoking-friendly rentals South Loop
- Monthly Rentals South Loop
- Rentals with an EV charger South Loop
- Rentals with lake access South Loop
- Rentals with a firepit South Loop
- Rentals with a hot tub South Loop
- Rentals with outdoor seating South Loop
- Rentals with a fireplace South Loop
- Apartment rentals South Loop
- Rentals with a patio South Loop
- Rentals with a washer and dryer South Loop
- Rentals with pools South Loop
- Fitness-friendly rentals South Loop
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom