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Compare 521 Vacation Homes in Oak Lawn with updated reviews, rates, and availability.

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

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

9.4 out of 10, Exceptional, (86)
"We rented this house so that two families could stay for the weekend in Chicago to celebrate our kids engagement. The house is great, it's pet friendly, it's in a great location, the garage is very useful for parking cars, etc. However, you really, really need to read the owner's rules. If you read the listing's first part "great place for your friends and family gathering", "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (2)
"Awesome stay!"
The price is AED 441
AED 1,128 total
includes taxes & fees
2 Feb - 3 Feb
Spacious 3br home near Chicago, fenced yard for pets

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway

Charming 3-bedroom house in Calumet City with WiFi and AC

10.0 out of 10, Exceptional, (3)
"Tammara is a perfect host! She is nice and accommodating. The check in process was very smooth. The house was spotless and so nice! I will definitely be booking again. "
The price is AED 551
AED 1,057 total
includes taxes & fees
7 Feb - 8 Feb
Charming 3-bedroom house in Calumet City with WiFi and AC

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.

Entire house 1 city block from Wrigley Field.

9.8 out of 10, Exceptional, (19)
"Very comfortable home close to Wrigley and to restaurants, coffee shop and shopping."
Entire house 1 city block from Wrigley Field.

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

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (73)
"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

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

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"Third time staying at this property. Great property and location. "
Cheery 2+bedroom home with free parking on premises

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

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!

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (38)
"Numerous problems that owner tried to fix-no wi-fi, no ac, broken upstairs dishwasher, basement flooded when we used downstairs washing machine. Place had not been cleaned prior to check in, trash sack in entry way, litter on floor, mop on back steps. Great location."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
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 Oak Lawn

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

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (426)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is AED 350
AED 411 total
includes taxes & fees
25 Feb - 26 Feb
Sonder South Wabash
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.