Search Vacation Homes in Oak Lawn

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Compare 525 Vacation Homes in Oak Lawn with updated reviews, rates, and availability.

Cozy Midway Home
2.0 star property
9.8 out of 10, Exceptional, (10)
"Really enjoyed staying here ! "
Cozy Midway Home
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
10.0 out of 10, Exceptional, (118)
"We were a group of 20 family members coming from all over the country for a wedding just a few blocks away. There was room for everyone, plus hairdryers, ironing board, iron, etc. needed to prepare for the big day. Target and Aldi, train station, and several coffee shops and restaurants, and parks within close walking distance made this the perfect location. Everyone loved staying here. We had good weather for porch sitting, and gathering outside after dark. Very helpful and available hosts too ...
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (15)
"Quiet and safe area with an L lline station only a few blocks away that made it very easy to get around the city. Lots of food options in the area."
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (20)
"The property owner David, was very quick in answering my questions through email and always answered his phone. The property was very clean. We found everything in order. There were plenty of towels, washclothes and toiletries. There was plenty of hot water for 4 adults. The kitchen had clean and simple utensils for our use. This property came with 2.5 bedrooms all dressed with fitted sheets, top sheets, and a comforter. Two pillows provided and the closets were spacious. The beds were...
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.8 out of 10, Exceptional, (12)
"Before and throughout the trip the hosts were very responsive and helpful. We fully booked the house and there was plenty of room for us in the common areas and backyard. The neighborhood around also has an excellent coffee shop, bar, and food areas within walking distance. Next time I bring a group to the Bridgeport area I’ll definitely try to book this property again "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
10.0 out of 10, Exceptional, (2)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
10.0 out of 10, Exceptional, (32)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
9.8 out of 10, Exceptional, (6)
"This is a very nice property. The only thing I caution is that it’s a 3rd floor walk up (actually on the 4th floor because there is nothing on the ground floor). "
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Wicker Park Entire House, Private Yard and Parking!
10.0 out of 10, Exceptional, (5)
"We loved this place. It was perfect for our work trip to Chicago. The neighborhood is awesome and the host was very organized and super easy to communicate with. Highly recommend this house!"
Wicker Park Entire House, Private Yard and Parking!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (79)
"Wish every stay was like this. Everything as As advertised and communication simple and open. Pleasure "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (79)
"This Old Town property was an excellent base for walking exploration of Lincoln Park (Saturday Farmer's Market was fantastic!) and Old Town itself (lively, with very good food, residential neighborhoods, shops, and entertainment), and had easy access to CTA trains to the Loop, Riverwalk, Millennium Park, and much more, had we had time. 7 adults (seniors) spent four nights, and found the four bedrooms, four bathrooms, large fully-equipped kitchen, and living/dining room/patio provided plenty of...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Spacious 5 BR / King Size Beds + Private Parking!
9.6 out of 10, Exceptional, (8)
"My coworkers and I came to Chicago for a conference and this was the perfect place to stay for it. The rooms were well separated so noise didn't travel between them, and the house was clean and comfortable. The host was extremely accommodating, and it was only a short distance from downtown Chicago."
Spacious 5 BR / King Size Beds + Private Parking!
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.2 out of 10, Wonderful, (7)
"The house was excellent for our family. It was definitely enough room and everything was okay for our trip. Neighborhood was nice and no one bothered us. "
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (13)
"My mom and I live in Huntsville Alabama and came to visit family and friends in the area and the Homewood house was the perfect location to stay. I miss home so much. It was very comfortable and cute. I will definitely make reservations for next year. Forget staying in a hotel. 😉😅"
Cozy Home Sweet Homewood.
5 minutes from Midway Int'l Airport Single Family Home.
9.0 out of 10, Wonderful, (4)
"Everything was fine. Owner was easy to work with and the property met our needs."
5 minutes from Midway Int'l Airport Single Family Home.
4 Mi to Dtwn Chicago: Modern Home w/ Outdoor Space
2.0 star property
4.0 out of 10, (1)
"This place looks nice in photos but is not ready for renting. It does not have a stocked kitchen or other basic amenities. Owner had to send glasses, silverware, hangers, iron, ironing board via Target on the second day of our stay. The dishwasher doesn’t work. Many of the drawers are broken. The deadbolt front door doesn’t lock from outside. "
4 Mi to Dtwn Chicago: Modern Home w/ Outdoor Space
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
2.0 star property
9.8 out of 10, Exceptional, (6)
"Perfect location outside of Chicago. We were visiting friends in nearby Hinsdale. Place is better than the photos. Easy check in process, great communication with host. Place is perfect, spotless and clean, seems brand new. Comfy beds. Keurig coffee was great. Would stay again. Highly recommend! ! "
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Spacious Deck & Balcony, Game Area, Garage
10.0 out of 10, Exceptional, (2)
"This is a large property--having not just 5 bedrooms, but lots of living space. We had plenty of room for a large group to stay and spread out. It had everything we needed."
The price is SAR 840
SAR 2,023 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Spacious Deck & Balcony, Game Area, Garage
Clarendon Hills Top Floor
6.6 out of 10, (4)
"This location is perfect for visiting the city and wanting not to stay in the city. The rooms accommodate a larger family or group. The tub had a slow drain and we couldn’t reach the host during our stay. They did reach out once our stay was over and apologized. Outside of the slow drain it was a great experience. I’m sure they will fix that soon. "
Clarendon Hills Top Floor
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, (576)
"Very nice place - great location"
The price is SAR 522
SAR 723 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (193)
"Not a lot of self cook food stores nearby "
The price is SAR 261
SAR 307 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
Sonder Market Hall
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (387)
"The apartment was nice. Maybe put a full length mirror in one of the bathrooms….when woman go out they want to look at themselves dressed up for an evening out. "
The price is SAR 518
SAR 608 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
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.