Oak Lawn Holiday Rentals

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Oak Lawn holiday rentals

Business centre
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1028)
"My favorite place to stay hands-down"
United States
Michele
The price is S$203
includes taxes & fees
5 Jan - 6 Jan, 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is S$198
includes taxes & fees
4 Jan - 5 Jan, 2026
Chicago luxury home suites
Living area
Wrigleyville Suites

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (27)
"Nice place "
United States
Barry
The price is S$149
includes taxes & fees
1 Jan - 2 Jan, 2026
Wrigleyville Suites
Private kitchen
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"Loved the space and location "
United States
Caroline
The price is S$300
includes taxes & fees
2 Jan - 3 Jan, 2026
River West, Third Floor 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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Great"
Jorge 5-night trip
Posted 15 hours ago
LondonHouse Chicago, Curio Collection by Hilton

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.