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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Oak Lawn holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1010)
"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
4 Jan - 5 Jan 2026
Sentral Michigan Avenue
Front of property – evening/night
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
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (650)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (390)
"Would certainly stay again. The business center was an unexpected bonus, along with the great view. "
Canada
Mark
Kasa South Loop Chicago
Front of property
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 ฿5,380
฿6,315 total
includes taxes & fees
19 Dec - 20 Dec
Chicago luxury home suites
Property entrance
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (225)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
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 ฿3,992
฿4,687 total
includes taxes & fees
19 Dec - 20 Dec
Wrigleyville Suites
Business centre
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
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 ฿2,397
฿2,708 total
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

Stylish Apartment near Chicago Downtown
2.0 star property
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
Art Villa
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great location! Nice view, good staff "
Carlos 1-night trip
Posted 22 hours ago
Hilton Chicago/Magnificent Mile Suites

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.