A cityscape with a river, high-rise buildings, and a bridge.

Oak Lawn Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Oak Lawn holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,283 reviews)
"Nice stay"
United States
Heather
The price is S$262
includes taxes & fees
8 Sept - 9 Sept
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is S$386
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (20 reviews)
"Great location and super clean!"
United States
Erica
The price is S$352
includes taxes & fees
9 Sept - 10 Sept
Kasa Lake Shore Chicago
A compact kitchen with a stainless steel refrigerator, wooden cabinets, a black leather sofa, and a small table.

4. River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (19 reviews)
"Loved the space and location "
United States
Caroline
The price is S$363
includes taxes & fees
27 Aug - 28 Aug
River West, Third Floor Chicago by 747 Lofts
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very good, (52 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is S$311
includes taxes & fees
8 Sept - 9 Sept
Wrigleyville Suites
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

6. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is S$435
includes taxes & fees
16 Sept - 17 Sept
The Oak Park Loft
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

7. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is S$565
includes taxes & fees
8 Sept - 9 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A red brick building with a blue awning and a sign reading "747 LOFTS."

8. 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, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is S$493
includes taxes & fees
30 Aug - 31 Aug
Chicago Third Floor Studio by 747 Lofts
A building with a white exterior and a tree with white blossoms in front.

9. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is S$420
includes taxes & fees
13 Sept - 14 Sept
Historic Oak Park Residence
A modern kitchen with wooden cabinets, a microwave, and a stove. There is a purple sofa and a small table with chairs. A suitcase is on the floor next to the sofa.

10. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is S$325
includes taxes & fees
10 Sept - 11 Sept
Chicago Second Floor Studio by 747 Lofts
A compact living space with a kitchenette, a sofa, a bed, and a television mounted on the wall.

11. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is S$232
includes taxes & fees
9 Sept - 10 Sept
Ground Floor Studios in Chicago by 747 Lofts
A modern interior with a large metallic chair, a glass table, and a black sofa.

12. Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
6.0 out of 10, (2 reviews)
"The code that was provided was incorrect. I was so anxious waiting outside the building until I was lucky that other guests were out and helped me get in. I tried reaching the “24/7” line but no response until a while and they had to reset everything before I was able to get in. First and last time I will be staying here. The bed is so small for even one person and the bathroom lights felt like a ghost was there. Do not book here, your anxiety will be through the roof !"
United States
Jamila
Cabin 105 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

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Very good location. Walking distance to many attractions. Clean no frills room. Smaller TV that wasn’t HD. Shower was older and water didn’t get very hot. Overall good experience. Liked old school classic feel of the hotel."
Andrew 1-night trip
Posted less than an hour ago
Congress Plaza Hotel

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 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.