Oak Lawn Holiday Rentals

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Check prices for these dates

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Oak Lawn

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is HK$784
HK$1,149 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (392)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (642)
"Clean facilities, great staff, good location "
United States
Emily
Kasa Magnificent Mile Chicago
Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (379)
"Completely equipped. Only issue was pots and pans which they resolved in a day. Will stay again."
United States
Thomas
Kasa South Loop Chicago
Property entrance
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is HK$1,366
HK$1,604 total
includes taxes & fees
4 Dec - 5 Dec
Chicago luxury home suites
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is HK$680
HK$798 total
includes taxes & fees
8 Dec - 9 Dec
Wrigleyville Suites
Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Lakeview
9.0 out of 10, Wonderful, (38)
"Perfect for our needs, clean, convenient and great value. "
United States
Lisa B.
The price is HK$467
HK$1,284 total
includes taxes & fees
8 Dec - 9 Dec
Clean & Equipped 1BR Apt
Desk, laptop workspace, blackout curtains, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
Harvey
3.8 out of 10, (67)
"Good "
United States
Abel
The price is HK$566
HK$639 total
includes taxes & fees
4 Dec - 5 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is HK$1,890
HK$3,023 total
includes taxes & fees
4 Dec - 5 Dec
Stylish Apartment near Chicago Downtown
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.6 out of 10, Excellent, (14)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
The price is HK$467
HK$1,206 total
includes taxes & fees
4 Dec - 5 Dec
Cozy Studio in Hyde Park-Walk to Lake & University
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview
9.2 out of 10, Wonderful, (27)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is HK$467
HK$1,411 total
includes taxes & fees
8 Dec - 9 Dec
Lakeview 2BR Apartment
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is HK$490
HK$1,312 total
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is HK$483
HK$1,419 total
includes taxes & fees
7 Dec - 8 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"This was a cute place with a lot of space. Nice backyard with areas to chill. The grand piano is beautiful and in tune!"
United States
Kenna C.
LakeHouse
Terrace/patio
Chicago Luxury Penthouse Gold Coast Best Location

Chicago Luxury Penthouse Gold Coast Best Location

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location
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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Top Oak Lawn Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Location of the Hotel is very nice and the hotel is very clean."
Khaing 1-night trip
Posted 8 hours ago
River Hotel

Find out more about Oak Lawn

Search for holiday rentals in Oak Lawn on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Lawn using one of the methods below:

  • View our selection of featured holiday rentals in Oak Lawn
  • Use the map to find apartments and other holiday homes in the Oak Lawn neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oak Lawn while they last

Look no further and take a look at our great range of rental properties in Oak Lawn!

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?

LakeHouse: This holiday home rental outside of Oak Lawn is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Oak Lawn?

Expedia has 6 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 Moraine Valley Community College Fine and Performing Arts Center, 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 Michigan Avenue and Wrigley Field.

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.