Oak Lawn Holiday Rentals

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Holiday Rentals in Oak Lawn

Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (20)
"Very cool penthouse apartment with two balconies and access to additional rooftop patio having amazing views of the Chicago skyline. Highly recommend!"
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
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Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is NZ$204
includes taxes & fees
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (176)
"Great stay! All of the rooms were wonderful! Really close to food! There are a lot of stairs so make sure you are able to walk up but really great place!"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Lobby
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is NZ$349
includes taxes & fees
27 May - 28 May
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (30)
"Beautiful, spacious, clean rooms. Cozy safe neighborhood. Prompt and responsive communication. Would absolutely stay here again!!"
The Neighborhood Hotel-Little Italy
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (37)
"Great access to Wrigley/ South Port & Lake view neighborhoods. Very Clean and laid out space that maximizes the space in this unit. Will be back soon!"
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (17)
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
The price is NZ$305
includes taxes & fees
22 May - 23 May
Chic Suite/Mins to L Train /Laundry/Free Parking
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is NZ$564
includes taxes & fees
19 May - 20 May
national historic home near downtown airports no parties no events
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (400)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is NZ$288
includes taxes & fees
27 May - 28 May
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (222)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
"Our team had a one day conference in Chicago. Although it was near the highway it wasn't very loud. Decent neighborhood and the good part is that it was near the highway. Lower level bed is uncomfortable, no other way to say that. I still give it 5-stars as it is as advertised. Communication with owner was timely."
The price is NZ$444
includes taxes & fees
19 May - 20 May
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is NZ$372
includes taxes & fees
28 May - 29 May
Sonder South Wabash
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See all available properties in Oak Lawn
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.

Other types of properties in Oak Lawn you may be interested in

View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2878)
"We stayed here for two nights and it was amazing! We will come back again)"
The price is NZ$311
includes taxes & fees
27 May - 28 May
River Hotel
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1002)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
The price is NZ$428
includes taxes & fees
23 May - 24 May
The Westin Michigan Avenue Chicago
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2586)
"I really enjoyed my stay, I felt safe and comfortable "
The price is NZ$226
includes taxes & fees
29 May - 30 May
Warwick Allerton - Chicago
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oak Lawn holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oak Lawn. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oak Lawn. Seeing all the best attractions is bound to make you fall in love with Oak Lawn. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oak Lawn short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Oak Lawn?

Yes, there are holiday rentals in Oak Lawn close to Childrens Museum of Oak Lawn, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Oak Lawn. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Oak Lawn has to offer?

Your Home Away From Home: This holiday home rental outside of Oak Lawn offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

How many holiday rentals are there in Oak Lawn?

Expedia has 11 holiday rentals for your stay in Oak Lawn.

What’s there to see and do in Oak Lawn?

Explore the area and cultural attractions such as Art Institute of Chicago, or visit one of the family-friendly sights such as Childrens Museum of Oak Lawn. In the wider area, you’ll find popular places such as Grant Park and Navy Pier.

What’s a holiday rental in Oak Lawn like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Lawn. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.

Recent reviews of Oak Lawn properties
Expedia verified reviews