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Oak Lawn Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Oak Lawn holiday rentals

Private kitchen

Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly and helpful. There was a massive storm before and the host accommodated us with everything we needed"
United States
Bailey H.
The price is HK$1,200
HK$1,468 total
includes taxes & fees
29 Jun - 30 Jun
Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,198 reviews)
"Great location"
United States
JAVIER
The price is HK$1,193
HK$1,631 total
includes taxes & fees
1 Jul - 2 Jul
Sentral Michigan Avenue
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is HK$2,117
HK$4,887 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Room

Full Bed | Non Smoking

Full Bed | Non Smoking
Markham
10.0 out of 10, Exceptional, (211 reviews)
"Solid place to crash after a long day."
United States
Anonymous traveller
Full Bed | Non Smoking
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.0 out of 10, Wonderful, (8 reviews)
"The parking situation is pretty rough. You have to park a half a mile away from the property. The room looks very luxurious in the pictures. However, once you get there, it does show some age and you can hear the other guest from above and below at all night not to mention that the city sounds are in full effect horns and traffic all night long and it’s difficult to get the room dark"
United States
Robert
The price is HK$1,819
HK$2,446 total
includes taxes & fees
1 Jul - 2 Jul
LIVN West Loop Chicago 2 BR City View
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,239
HK$1,648 total
includes taxes & fees
30 Jun - 1 Jul
LIVN Millennium Park Downtown Chicago Studio
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is HK$1,785
HK$2,289 total
includes taxes & fees
30 Jun - 1 Jul
Level Chicago – Old Town
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 1

Beautiful Unit CHI in Prime River North - 1
Downtown Chicago
9.2 out of 10, Wonderful, (23 reviews)
"Location was fun"
United States
Robert L.
The price is HK$1,294
HK$3,464 total
includes taxes & fees
3 Jul - 4 Jul
Beautiful Unit CHI in Prime River North - 1
Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (82 reviews)
"Great location for a short trip "
United States
Eric W.
The price is HK$1,248
HK$2,847 total
includes taxes & fees
30 Jun - 1 Jul
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Property grounds

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (27 reviews)
"I had a fun stay "
United States
Jusu K.
The price is HK$1,263
HK$1,758 total
includes taxes & fees
1 Jul - 2 Jul
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Dining

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"My group and I traveled to town this weekend for a music festival and had the opportunity to stay at this place and had a great time. Communication with the host was very prompt when we had any questions which I appreciate a lot. Also, the place was clean and spacious for our group and easy to come in and out. Would recommend this place to others looking for a place to stay in town."
United States
Marcos B.
The price is HK$714
HK$3,205 total
includes taxes & fees
21 Jul - 22 Jul
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is HK$1,670
HK$4,201 total
includes taxes & fees
19 Jul - 20 Jul
River North Rooftop With In and Out Parking 6
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
Downtown Chicago Stay with Free In & Out Parking 5
TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is HK$1,874
HK$3,895 total
includes taxes & fees
26 Jul - 27 Jul
River North Rooftop With In and Out Parking 1
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is HK$980
HK$1,693 total
includes taxes & fees
28 Jul - 29 Jul
Cozy studio in Andersonville Chicago
Interior

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is HK$627
HK$2,402 total
includes taxes & fees
13 Jul - 14 Jul
Sleeps 7 • Huge Projector • Designated Workspace
Interior

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (101 reviews)
"Everything was good!"
United States
Brio
The price is HK$1,277
HK$2,567 total
includes taxes & fees
5 Jul - 6 Jul
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Fridge, microwave, oven, stovetop

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is HK$1,200
HK$2,747 total
includes taxes & fees
30 Jun - 1 Jul
Cozy, Comfortable and Convenient apartment. Close to everything!
1 bedroom

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is HK$893
HK$988 total
includes taxes & fees
29 Jun - 30 Jun
2 Full Beds | Non-Smoking, Kitchen
TV, offices

Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
The price is HK$2,313
HK$5,972 total
includes taxes & fees
6 Jul - 7 Jul
Modern West Loop Gem-City Views & Prime Location 1
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great view from the room"
Uri 4-night trip
Posted 1 hour ago
Hyatt Regency Chicago

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
  • Use the map to find apartments and other holiday homes in the Oak Lawn neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oak Lawn while they last

Look no further and take a look at our great range of rental properties in Oak Lawn!

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 Michigan Avenue.

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.