Oak Lawn Vacation Rentals

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Check prices for these dates

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

Our top choices for Oak Lawn vacation rentals

Business center
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
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, (408)
"Great location, clean room and friendly staff!"
United States
Scott
The price is ￥29,590
￥38,226 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1028)
"My favorite place to stay hands-down"
United States
Michele
The price is ￥17,149
￥24,721 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
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 ￥20,531
￥24,101 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Chicago luxury home suites
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (17)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥10,762
￥29,714 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Twice as Nice: Chic 2BR Stay with Style & Space
Interior
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 out of 10, Exceptional, (4)
"Great stay. I'm from the area but had friends visiting from out of town. This was a great location only a quick walk to Michigan Avenue and 15 minutes from the loop. The apartment was spacious, and I appreciated having disney plus/netflix signed into the TV. The check-in and check-out was really easy with an accompanying video and easy lockbox location. Host/company was also very communicative, and let me grab something I forgot in my rental after checking out!Parking space was also clutch, just...
United States
Amarah K.
The price is ￥15,638
￥49,125 total
includes taxes & fees
Jan 5 - Jan 6, 2026
River North Rooftop With In and Out Parking 3
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ￥10,762
￥25,815 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥9,852
￥26,347 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is ￥9,826
￥26,278 total
includes taxes & fees
Jan 20 - Jan 21, 2026
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ￥9,826
￥26,278 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Sun-Drenched 1BR Apartment
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥9,852
￥26,347 total
includes taxes & fees
Jan 1 - Jan 2, 2026
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ￥9,852
￥26,347 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The One: A 1BR Stay That Feels Like Home
Interior
Chicago-Themed 1BR in a Central Spot near Downtown

Apartment in Downtown Chicago

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
The price is ￥9,852
￥26,347 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Chicago-Themed 1BR in a Central Spot near Downtown
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ￥9,852
￥26,347 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Sleek 1BR Apt w/ Laundry
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Apartment in Hyde Park

Modern Studio Near UChicago
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥8,914
￥23,684 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Modern Studio Near UChicago
3 bedrooms, iron/ironing board, travel crib, WiFi
Sleek Style 3BR Haven - Free Parking

Apartment in Lincoln Park

Sleek Style 3BR Haven - Free Parking
9.8 out of 10, Exceptional, (30)
"Awesome place to stay. "
United States
Gary
The price is ￥12,322
￥39,908 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Sleek Style 3BR Haven - Free Parking
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (27)
"Nice place "
United States
Barry
The price is ￥15,482
￥18,174 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Wrigleyville Suites
TV, offices
Complete 1BR Home Sum

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is ￥9,852
￥26,347 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Complete 1BR Home Sum
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Loved the space and location "
United States
Caroline
The price is ￥13,438
￥36,517 total
includes taxes & fees
Jan 2 - Jan 3, 2026
River West, Third Floor Chicago by 747 Lofts
Iron/ironing board, travel crib, bed sheets
Stylish Japanese-Themed 2BR Apt Close to Downtown

Apartment in Downtown Chicago

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
The price is ￥10,790
￥29,792 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Stylish Japanese-Themed 2BR Apt Close to Downtown
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
"Front desk staff was courteous and very helpful."
Albert 1-night trip
Posted 1 day 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
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Look no further and take a look at our great range of rental properties in Oak Lawn!

Frequently asked questions

Can I find a vacation rental in Oak Lawn?

Yes, you can find vacation rentals in Oak Lawn close to Childrens Museum of Oak Lawn, or you can go with 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 vacation home rentals that Oak Lawn has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Oak Lawn vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Oak Lawn?

Expedia has 7 vacation 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 a family-friendly sight such as Childrens Museum of Oak Lawn. In the larger area, you’ll find popular places like Michigan Avenue and Wrigley Field.

What’s a vacation rental in Oak Lawn like?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Oak Lawn. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip.