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Oak Lawn Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Oak Lawn holiday rentals

A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

1. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
The price is AU$288
includes taxes & fees
5 Oct - 6 Oct
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Private kitchen

2. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is AU$321
includes taxes & fees
8 Oct - 9 Oct
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

3. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (33 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is AU$263
includes taxes & fees
13 Oct - 14 Oct
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

4. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (80 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AU$461
includes taxes & fees
2 Nov - 3 Nov
Cozy, Comfortable and Convenient apartment. Close to everything!
A rooftop terrace with a brick wall, large windows, and a metal railing.

5. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is AU$394
includes taxes & fees
5 Oct - 6 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

6. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Great place to stay "
United States
Harquesha S.
The price is AU$261
includes taxes & fees
13 Oct - 14 Oct
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A rooftop terrace with a brick wall, large windows, and a metal railing.

7. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (29 reviews)
"Was a great and clean place to stay.. "
United States
Ashly B.
The price is AU$394
includes taxes & fees
5 Oct - 6 Oct
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a blue sofa, a patterned rug, and a television.

8. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is AU$300
includes taxes & fees
13 Oct - 14 Oct
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern building with the name 'SENIORAL' prominently displayed on the facade.

9. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,348 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
The price is AU$339
includes taxes & fees
26 Oct - 27 Oct
Sentral Michigan Avenue
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

10. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
The price is AU$406
includes taxes & fees
14 Oct - 15 Oct
Private Workspace • Sleeps4 • Modern Stylish Stay
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

11. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (71 reviews)
"Easy access to the Green Line."
United States
Michael
The price is AU$364
includes taxes & fees
2 Nov - 3 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

12. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is AU$284
includes taxes & fees
12 Oct - 13 Oct
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

13. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (7 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is AU$447
includes taxes & fees
14 Oct - 15 Oct
Sleeps 7 • Huge Projector • Designated Workspace
A modern bedroom with a bed, a sofa, and a hanging plant.

14. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (99 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
The price is AU$212
includes taxes & fees
26 Oct - 27 Oct
Cozy studio in Andersonville Chicago
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

15. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is AU$393
includes taxes & fees
5 Oct - 6 Oct
3BR Complete and Spacious Apartment in Ideal Spot
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

16. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is AU$118
includes taxes & fees
16 Oct - 17 Oct
2 Full Beds | Non-Smoking, Kitchen
Lake

17. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (49 reviews)
"Location is perfect"
United States
Mary
The price is AU$426
includes taxes & fees
2 Nov - 3 Nov
Kasa Lake Shore Chicago
A modern living room with a large white table, grey sofa, and a flat-screen TV mounted on the wall.

18. King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (10 reviews)
"Adorable place to stay, decor is done so cute. Very comfortable family room to relax"
United States
Teresa S.
The price is AU$379
includes taxes & fees
4 Oct - 5 Oct
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

19. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is AU$442
includes taxes & fees
5 Oct - 6 Oct
2BR Apt with 2 Baths & Laundry
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

20. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is AU$367
includes taxes & fees
13 Oct - 14 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Great experience on my first trip to Chicago"
Gary 5-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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$104 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Oak Lawn is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Soldier Field and Navy Pier.

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.