Photo by Erik Rowley

Search Vacation Homes in South Suburbs

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in South Suburbs

Our top choices for South Suburbs vacation homes

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (50)
"Great bang for your buck. Great area and great communication "
Belmont House, Classy & Chic/walk to Wrigley Field

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (53)
"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

LUXE 3 BR, 2 BA + Hot Tub

8.8 out of 10, Excellent, (33)
"The house had a lot of gnats and we were bit up"
The price is SAR 759
SAR 1,483 total
includes taxes & fees
29 Sep - 30 Sep
LUXE 3 BR, 2 BA + Hot Tub

Theater • Game Room • Gym • Firepit • 4BR Home

7.6 out of 10, Good, (10)
"Comfy beds and a great house for kids and adults."
The price is SAR 244
SAR 1,903 total
includes taxes & fees
30 Sep - 1 Oct
Theater • Game Room • Gym • Firepit • 4BR Home

A Home Away From Home!

9.6 out of 10, Exceptional, (11)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Full entire cozy home + Free Wi-Fi + Free parking + Central area

6.0 out of 10, (1)
"The pictures are accurate as seen on the website . However, the amenities left a lot to be desired. The six bath towels were good and the 7 washcloths were horrible as some had bleach stains on them and they were very thin. No hand towels were provided to dry your hands on in the bathroom. Nor were there paper towels in the bathroom for that purpose. The other rooms were clean but the bathroom needs a deep cleaning . No cleaning products were provided either. "
Full entire cozy home + Free Wi-Fi + Free parking + Central area

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.0 out of 10, Wonderful, (12)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is SAR 851
SAR 1,704 total
includes taxes & fees
28 Sep - 29 Sep
Spacious 3br home near Chicago, fenced yard for pets

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

2.0 star property
9.8 out of 10, Exceptional, (12)
"We loved Retro House, a real treasure inside Chicago. Comfortable, quiet and safe."
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

2BR Traveler`s Favorite • Modern and Clean

10.0 out of 10, Exceptional, (1)
"The place was really nice and clean, an excellent stay that ill consider again my next trip to chicago"
2BR Traveler`s Favorite • Modern and Clean

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (9)
"Great"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

Wrigley Field/Lakeview -Entire Home- Large Groups!

10.0 out of 10, Exceptional, (83)
"This was the perfect stay for our family while we were in town for our daughter's graduation. The house was plenty big to accommodate our group, and the location is excellent. The host was very accommodating and easy to get in touch with. It was one of our best VRBO experiences yet."
Wrigley Field/Lakeview -Entire Home- Large Groups!

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

9.8 out of 10, Exceptional, (176)
"Great place for our large group. Lots of room for the bridal girls to get ready for the wedding. "
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

9.8 out of 10, Exceptional, (27)
"Great location that was walking distance to everything we needed. There was more than enough room for our group and it was a comfortable stay."
Inspiring Stone Grotto Sleeps 10-20 & Free Parking

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (11)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (60)
"The stay was excellent. "
Great 3 bedroom rental unit near Logan Square

Historic luxury townhouse on Chicago's Gold Coast

9.4 out of 10, Exceptional, (74)
"Large houseClean and well furnishedMix-up on checkin but manager on site fixed quickly.I highly recommend and would stay here again"
Historic luxury townhouse on Chicago's Gold Coast

Charming Full Modern Home+Free Parking+Fast Wi-Fi & Centrally located

4.0 out of 10, (1)
"The house was normal. No major issues. We were told there would be a washer and dryer, but it did not have one accessible. It appeared to be in the garage, but the garage was locked and no one would respond.Our check in was 3:00 pm on Friday, at noon on Friday the company managing the property tetzy? told me that I needed to provide everyones first and last name and their cell phone. Seemed strange. 1. Why wait until the last minute and 2. Why do you need everyone's contact? I saw this request,...
Charming Full Modern Home+Free Parking+Fast Wi-Fi & Centrally located

Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home

5.0 out of 10, (4)
"Nice stay overall easy check in and check out. Some guests had complaints about bed and furniture comfort and quality. "
Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

2.0 star property
10.0 out of 10, Exceptional, (14)
"I had an excellent experience. I plan to book again. "
The price is SAR 889
SAR 1,991 total
includes taxes & fees
24 Sep - 25 Sep
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top South Suburbs Hotel Reviews