Oak Lawn Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oak Lawn holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1005)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is AU$253
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (396)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"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 AU$186
includes taxes & fees
11 Dec - 12 Dec
Chicago luxury home suites

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 AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish 1BR in West Loop

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

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)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AU$310
includes taxes & fees
11 Dec - 12 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
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 AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Sun-Drenched 1BR Apartment

Your Chicago get Away

Your Chicago get Away
Downtown Chicago
8.4 out of 10, Very good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AU$622
includes taxes & fees
11 Dec - 12 Dec
Your Chicago get Away

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
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 AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"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 AU$252
includes taxes & fees
4 Jan - 5 Jan 2026
Gold Coast Living: Modern Studio Unit

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
2.0 star property
Downtown Chicago
8.0 out of 10, Very good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is AU$485
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
The One: A 1BR Stay That Feels Like Home

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
Chicago Third Floor Studio by 747 Lofts

Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6
2.0 star property
Downtown Chicago
The price is AU$604
includes taxes & fees
22 Dec - 23 Dec
Downtown Chicago Stay with Free In & Out Parking 6

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is AU$664
includes taxes & fees
19 Dec - 20 Dec
South Loop Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
River North Rooftop With In and Out Parking 1

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
The price is AU$236
includes taxes & fees
11 Dec - 12 Dec
Modern Studio Near UChicago

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
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 traveller
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek 1BR Apt w/ Laundry

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is AU$563
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oak Lawn Hotel Reviews

Find out more about Oak Lawn

Everything you need to know about Oak Lawn holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Lawn holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Lawn holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oak Lawn holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Lawn. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Lawn holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Lawn holiday rentals we have selected for you start as low as AU$143 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oak Lawn rentals

At Expedia, we put the best Oak Lawn holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Lawn rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Lawn holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Lawn. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.