House vacation rentals in South Loop, Chicago

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Popular amenities for South Loop, Chicago house rentals

House rentals with a pool

Home in The Loop
5 out of 5 average rating, 6 reviews

Luxury Condo Downtown Chicago

CarsonRating, 5 stars16 months ago
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.
Superhost
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars2 months ago
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.
Home in Lockport
4.75 out of 5 average rating, 4 reviews

Hidden GEM OASIS in Chicagoland

JustinRating, 5 stars2 months ago
Great place to stay in the Chicago area. Somewhat rural but everything is close. Perfect for our family.
Superhost
Home in Bloomingdale
4.93 out of 5 average rating, 44 reviews

No Cleaning Fee - Whole House With Hot Tub

ChristopherRating, 5 stars1 month ago
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.
Superhost
Home in Lincoln Park
4.87 out of 5 average rating, 53 reviews

Luxury Cabin in Lakeview

Varun Rating, 5 stars6 months ago
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!
Home in Austin
New place to stay

4Bed GemW/Pool for8 Near ORD/MDW

LorpuRating, 5 stars2 weeks ago
Very great place, exactly like the photos and description!! House was nice and spacious. On top that great location.
Superhost
Home in Schaumburg
4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

LindsayRating, 5 stars2 months ago
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

Guest favourite
Home in West Lawn
4.94 out of 5 average rating, 35 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JessieRating, 5 stars3 weeks ago
Very nice, homey place. We felt right at home! Nice, quiet neighborhood.
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 273 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

marcioRating, 5 stars1 week ago
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.
Guest favourite
Home in Glen Ellyn
4.92 out of 5 average rating, 141 reviews

Home in Glen Ellyn

Venkata Pushyahass ReddyRating, 5 stars1 month ago
It’s a nice place as described. Our stay was pleasant.
Guest favourite
Home in Lansing
4.82 out of 5 average rating, 116 reviews

Cozy at the Walter

TehaniRating, 5 stars3 weeks ago
Our go to in the Chicagoland area.... always a pleasure to stay at The Walter
Top guest favourite
Home in Wicker Park
4.97 out of 5 average rating, 31 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

SpencerRating, 5 stars2 months ago
Tom was great, friendly, and very helpful, highly recommend
Guest favourite
Home in Avondale
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars5 months ago
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!
Superhost
Home in Whiting
4.84 out of 5 average rating, 147 reviews

The Spa of Downtown Whiting

JaniceRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Lake View
4.95 out of 5 average rating, 182 reviews

Wrigleyville Greystone

MarkRating, 5 stars2 months ago
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

Superhost
Home in Oak Park
5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars2 months ago
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.
Superhost
Home in Chicago
4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

ErnestoRating, 5 stars6 months ago
Nice house 🔥
Guest favourite
Home in Schaumburg
4.96 out of 5 average rating, 54 reviews

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd

KinseyRating, 5 stars3 days ago
Perfect for our work trip!
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars4 months ago
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.
Superhost
Home in Austin
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars4 months ago
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.
Superhost
Home in Blue Island
4.81 out of 5 average rating, 190 reviews

Warm and comfortable inviting Suburban home !

LuCindaRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Chicago Ridge
4.93 out of 5 average rating, 116 reviews

Quiet cul-de-sac with huge fenced in backyard

LatrinaRating, 5 stars2 weeks ago
Most amazing place to stay 5/5 would recommend.
Superhost
Home in Near West Side
4.84 out of 5 average rating, 494 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

AshliRating, 5 stars3 days ago
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.

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