Search Holiday Rentals in Oak Lawn

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Oak Lawn holiday rentals

Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ฿3,717
฿5,287 total
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Fridge, microwave, oven, stovetop
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
7.4 out of 10, Good, (3)
"Do not book. This is a scam you will be asking to zelle a several hundred dollar security deposit after paying in full and before check in. You’ll receive sketchy FaceTime audio calls and messages from several different numbers requesting this. "
United States
Brooke
The price is ฿3,400
฿3,991 total
includes taxes & fees
18 Dec - 19 Dec
Chicago luxury home suites
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ฿3,655
฿4,290 total
includes taxes & fees
18 Dec - 19 Dec
Wrigleyville Suites
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge
Historic Oak Park Home

Apartment in Oak Park

Historic Oak Park Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ฿5,522
฿9,817 total
includes taxes & fees
18 Dec - 19 Dec
Historic Oak Park Home
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior
Historic Oak Park Residence

Apartment in Oak Park

Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
The price is ฿5,666
฿9,983 total
includes taxes & fees
18 Dec - 19 Dec
Historic Oak Park Residence
Studio | Interior
Cabin 105 by 747 Lofts

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ฿2,023
฿4,430 total
includes taxes & fees
30 Dec - 31 Dec
Cabin 105 by 747 Lofts
View from property
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is ฿28,219
฿39,741 total
includes taxes & fees
18 Dec - 19 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is ฿4,971
฿12,977 total
includes taxes & fees
4 Jan - 5 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
4.0 out of 10, (68)
"Good "
United States
Abel
The price is ฿2,395
฿2,706 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms
The Oak Park Loft

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ฿4,862
฿9,060 total
includes taxes & fees
18 Dec - 19 Dec
The Oak Park Loft
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Friendly/Helpful staff made for a great welcome! "
Lisa 2-night trip
Posted 5 hours ago
Crowne Plaza Chicago West Loop by IHG

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.

How many holiday rentals are there in Oak Lawn?

Expedia has 7 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.