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Search Vacation Homes in South Suburbs

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Compare 329 Vacation Homes in South Suburbs with updated reviews, rates, and availability.

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (86)
"Location of house is great, communication with owner is great. The house "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (38)
"Very comfortable and welcoming. a great stay for a large family. We enjoyed everything about our stay. Will be back!"
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.8 out of 10, Exceptional, (6)
"Great location so convenient to everything! Great to have a garage to park. Also, great to have the 2 bedrooms with their own bathrooms! Property met our needs. It was not dirty but was not as clean as it could have been. (Mainly the floors) Overall the house worked great for us! "
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Staycation Retreat

2.0 star property
6.4 out of 10, (5)
"My stay was good it was spacious was cuteee ! And perfect for my group !"
The price is AED 437
AED 893 total
includes taxes & fees
4 Feb - 5 Feb
Staycation Retreat

Berwyn Beauty

10.0 out of 10, Exceptional, (12)
"Perfect for visiting family by with more space than an hotel. A nice neighborhood. Away from the hustle and bustle of downtown but an easy drive for vacationers. "
Berwyn Beauty

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Nestled just behind Marquette Park. 5 minute walk to beach.

10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"Location is great, size of the house is great with queen beds in all room and even one with a King bed. Basement was very cold, ( it’s winter) so that bedroom was not used but wasn’t needed anyways. The house needs a really good cleaning especially the kitchen especially the cabinets. Also coffee maker is tiny, doesn’t make sense considering the size of the house. Ironing board had no cover just metal frame, kitchen was not stocked properly for the size of the house. Loved the fact there was...
Stunning / Spacious 6BD Home + garage - Bucktown!

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (46)
"The home was updated and very clean. The kitchen was large and was well stocked. The owner provided everything you would need to cook. The fenced in yard was a bonus as we traveled with our dog. The neighborhood is older and safe. The neighboring homes are well maintained. The street in front of the house is busy during rush hour, but didn't create an issue pulling out into traffic. We did not experience noise from the traffic. We had one small glitch which was taken care of quickly. The...
The price is AED 584
AED 1,306 total
includes taxes & fees
24 Feb - 25 Feb
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

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

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (44)
"Fantastic house…whole family enjoyed our stay. Thank you!"
Luxury House in the heart of Old Town with Parking

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (21)
"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"
The price is AED 1,010
AED 1,688 total
includes taxes & fees
9 Feb - 10 Feb
LUXE 3 BR, 2 BA + Hot Tub

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (2)
"This was a great rental experience from start to finish. Everyone was impressed with the space, and the location couldn't be better. We will definitely be back. "
Spacious 5-bedroom house with movie room, game room and more!

Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

10.0 out of 10, Exceptional, (33)
"We had a terrific stay at here. The apartment was sparkly clean. The linens were like new. The bed was comfortable and cozy. It’s a basement apartment but you don’t feel “underground” at all. It’s light and airy, laid out well with plenty of living space. It’s on a quiet residential block and conveniently located for public transportation and walking to restaurants. Caitlin checked in with us just the right amount—to be sure the temperature was right (it was) and if we needed anything (we...
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
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.
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Other property types in South Suburbs

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (18)
"It felt like home. Didnt want to leave."
Cozy Home Sweet Homewood.

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (670)
"Sandra and Joy are welcoming and helpful. Great front desk."
The price is AED 403
AED 581 total
includes taxes & fees
3 Feb - 4 Feb
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (250)
"Enjoyed My Stay."
The price is AED 415
AED 487 total
includes taxes & fees
24 Feb - 25 Feb
Sonder Market Hall
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.