Oak Lawn holiday rentals

We found 600 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Oak Lawn that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a fireplace. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Oak Lawn

Showing deals for:18 Dec - 25 Dec

Private kitchen
Interior
Living area
Room
Exceptional
(9 reviews)

Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!

Chicago

7% off
AU$5,794
for 7 nights, 1 home
AU$828 per night
includes taxes & fees
Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!
Dining
Interior
Living area
Room
Exceptional
(40 reviews)

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

Berwyn

8% off
AU$2,803
for 7 nights, 1 apartment
AU$400 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Dining
Room
Private kitchen
Interior
Very good
(11 reviews)

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Chicago

7% off
AU$2,410
for 7 nights, 1 apartment
AU$344 per night
includes taxes & fees
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Living area
Dining
Living area
Interior
Exceptional
(15 reviews)

Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks

Burr Ridge

8% off
AU$5,378
for 7 nights, 1 home
AU$768 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
Private kitchen
Living area
Dining
Room
Exceptional
(22 reviews)

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

Berwyn

8% off
AU$2,487
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Living area
Room
Interior detail
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$4,044
for 7 nights, 1 apartment
AU$578 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Living area
Interior
Dining
Living area
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$2,487
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Interior
Exterior detail
Room
Interior
Excellent
(10 reviews)

Charming 2-bedroom 1 bathroom Bridgeport Chicago

Chicago

7% off
AU$2,214
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Charming 2-bedroom 1 bathroom Bridgeport Chicago
Room
Dining
Living area
Private kitchen
Wonderful
(21 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$2,429
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Room
Living area
Interior
Interior
Exceptional
(7 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$4,421
for 7 nights, 1 apartment
AU$632 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Living area
Exterior
Living area
Room
Exceptional
(108 reviews)

Lg Studio Apt. No cleaning fee. Obama Center 10 mins.

Chicago

8% off
AU$1,485
for 7 nights, 1 apartment
AU$212 per night
includes taxes & fees
Lg Studio Apt. No cleaning fee. Obama Center 10 mins.
Living area
Exterior
Games room
Private kitchen
Very good
(31 reviews)

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago

7% off
AU$1,262
for 7 nights, 1 apartment
AU$180 per night
includes taxes & fees
Peaceful place Great location food markets transportation downtown lake Michigan
Private kitchen
Exterior detail
Dining
Interior
Exceptional
(11 reviews)

Historic feel, Modern comfort Walk to parks and food in beautiful Chicago

Chicago

6% off
AU$1,945
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Interior
Living area
Room
Private kitchen
Very good
(5 reviews)

Chicago style apt/Near Hosp/ORD/MDW/DT

Berwyn

8% off
AU$2,454
for 7 nights, 1 apartment
AU$351 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Smart tv and wifi available
Private kitchen
Dining
Exterior
Exceptional
(27 reviews)

Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed

Chicago

7% off
AU$2,166
for 7 nights, 1 home
AU$309 per night
includes taxes & fees
Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
Private kitchen
Property grounds
Interior
Room
Exceptional
(7 reviews)

3bed/1 bath Retreat - 10 min from Downtown

Chicago

7% off
AU$3,031
for 7 nights, 1 apartment
AU$433 per night
includes taxes & fees
3bed/1 bath Retreat - 10 min from Downtown
Interior
Living area
Dining
Exterior
Exceptional
(7 reviews)

Stylish 2BR Near Hyde Park, UChicago & Lake

Chicago

7% off
AU$2,840
for 7 nights, 1 apartment
AU$406 per night
includes taxes & fees
Stylish 2BR Near Hyde Park, UChicago & Lake
Interior
Private kitchen
Private kitchen
Room
Exceptional
(8 reviews)

Chic 1-bedroom apartment,15mims from downtown

Chicago

7% off
AU$1,648
for 7 nights, 1 apartment
AU$235 per night
includes taxes & fees
Chic 1-bedroom apartment,15mims from downtown
Bathroom
Room
Dining
Living area
Exceptional
(13 reviews)

Chic & Cozy near ORD>MDW>DT>HOSP

Berwyn

8% off
AU$3,188
for 7 nights, 1 apartment
AU$455 per night
includes taxes & fees
Chic & Cozy near ORD>MDW>DT>HOSP
Property grounds
Living area
Dining
Room
Wonderful
(8 reviews)

Great Location. 5min to McCormick place. Downtown. Chinatown

Chicago

7% off
AU$2,921
for 7 nights, 1 apartment
AU$417 per night
includes taxes & fees
Great Location. 5min to McCormick place. Downtown. Chinatown
Room
Living area
Private kitchen
Exterior
Exceptional
(8 reviews)

High-end 2Bdrm Garden Apt. Where Comfort Meets Style

Chicago

7% off
AU$2,675
for 7 nights, 1 apartment
AU$382 per night
includes taxes & fees
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Interior
Dining
Dining
Room
Exceptional
(32 reviews)

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

Berwyn

8% off
AU$2,172
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

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Why people love visiting lively Oak Lawn

Enjoy the musicals and other features of Oak Lawn. Travellers to this welcoming city praise the restaurants, shopping and baseball games. McCormick Place and Soldier Field are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Oak Lawn

Are you hoping to discover things to do while you're in town? Venture out of your holiday home and check out everything that Oak Lawn has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Harborside International Golf Center (8 mi / 12.9 km)
  • Cog Hill Golf & Country Club (11 mi / 17.7 km)
  • Ravisloe Country Club (11.7 mi / 18.8 km)
  • Lincoln Park Zoo (15.1 mi / 24.3 km)
  • Chicago State University (7.1 mi / 11.5 km)
  • Galloping Ghost (8.7 mi / 14 km)

Exploring the natural landscape of Oak Lawn

Whether you're an active traveller or just want to appreciate the scenery, Oak Lawn is a great place to get outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (13 mi / 20.9 km)
  • Grant Park (12.5 mi / 20 km)
  • Abbott Park (6.5 mi / 10.4 km)
  • Jackson Park (9.6 mi / 15.4 km)
  • Anna and Frederick Douglass Park (10.2 mi / 16.4 km)
  • Rainbow Beach (10.8 mi / 17.4 km)

Travelling to and around Oak Lawn

Fly into Chicago Midway Airport (MDW), the closest airport, located 4.7 mi (7.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago O'Hare International Airport (ORD), which is 19.5 mi (31.4 km) away.

If you're travelling by train, the main station is Oak Lawn Station.

Frequently asked questions

What is the best area to stay in Oak Lawn when booking a holiday rental?
When booking a holiday rental in Oak Lawn, Illinois, a great area to consider is the vicinity around the Oak Lawn Village Centre. This neighbourhood is not only well-connected by public transport but also offers a vibrant setting with a mix of local shops and eateries. A highlight of the area is the Oak Lawn Community Park District, which features beautiful parks and recreational facilities superb for families.Another appealing option is the area near the Chicago Ridge Mall, which is just a short drive away. This neighbourhood provides easy access to shopping and dining, making it convenient for visitors looking to explore local cuisine or indulge in a bit of retail therapy. The mall also hosts various events throughout the year, adding to the lively community spirit.While the exact number of holiday rental properties can vary, Oak Lawn generally offers a diverse range of options, from cosy apartments to spacious homes, suiting different preferences and budgets.
What is the most popular type of holiday rental accomodation in Oak Lawn?
In Oak Lawn, holiday houses are the most popular type of holiday rental, with about 15 available throughout the area. These houses typically offer spacious living spaces, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many also feature private backyards or patios for outdoor relaxation. Additionally, there are several condos and apartments, which provide a more compact option for travellers who prefer a simpler, yet cosy accommodation.
Are there any family house rentals in Oak Lawn?
In Oak Lawn, Illinois, there are several family-friendly house rentals available, making it a great choice for those travelling with children. This suburban area offers spacious homes that often come equipped with multiple bedrooms, making it convenient for families. Many properties include essential amenities such as fully equipped kitchens, allowing for easy meal preparation, as well as comfortable living areas where everyone can gather.Visitors can also enjoy outdoor spaces, which may feature gardens or patios, ideal for kids to play or for family barbecues. The locale is just a short drive from various parks and recreational areas, where families can enjoy outdoor activities, picnics, and playground fun. Additionally, attractions in nearby Chicago are easily accessible, offering even more options for family outings.
Are there pet-friendly house rentals in Oak Lawn?
In Oak Lawn, there are several pet-friendly house rentals available, making it a great choice for travellers wishing to bring their furry companions along. Many of these properties come equipped with modern amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces, ideal for both relaxation and entertaining.The neighbourhood itself is well-suited for pet owners, with nearby parks providing ample space for walks and play. The expansive Oak Lawn Park District includes several parks where pets are welcome, allowing for enjoyable outings. This community-centric atmosphere, combined with the convenience of local shops and restaurants, enhances the overall experience for visitors.
Are there any remote work holiday rentals in Oak Lawn?
In Oak Lawn, Illinois, there are a number of holiday rentals suitable for remote work, with approximately 18 options available. These properties cater well to those needing to balance work and leisure, featuring amenities such as free in-room Wi-Fi and dedicated workspaces equipped with desk chairs and computer monitors. This ensures a comfortable and productive environment for remote workers.The area is conveniently located near various local attractions, including parks and dining options, allowing for a pleasant break after work hours. Families will appreciate the spacious rooms, which often include full kitchens and living areas, providing a cozy feel. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oak Lawn?
In Oak Lawn, popular holiday rental amenities cater to various needs and preferences. Many properties offer onsite parking, which is particularly convenient for those travelling by car. Additionally, rentals typically come equipped with kitchens, allowing guests to prepare their own meals during their stay. For those who enjoy cooking, having a blender available adds to the convenience. Furthermore, pet-friendly options are common, enabling travellers to bring their pets along, including service animals.
When is the best time to visit Oak Lawn for a holiday rental?
The peak season for visiting Oak Lawn is from May to July, when the vibrant summer atmosphere draws in travellers. This period is particularly popular as the weather is pleasantly warm, with temperatures typically ranging from mid-teens to low 30s Celsius, making it ideal for outdoor activities and local festivals. Visitors can enjoy a variety of attractions, including the beautiful parks and recreational areas that Oak Lawn has to offer, as well as nearby Chicago's bustling city life.July stands out as the most popular month, with a lively ambiance as locals and tourists come together for summer events and activities. The long days are great for exploring the local culture, from dining at outdoor cafes to participating in community gatherings.For those seeking a more budget-friendly option, consider visiting in November. This quieter month allows for a more relaxed experience, where you can enjoy the crisp autumn air and beautiful fall foliage without the crowds. The local parks provide a serene setting for leisurely walks, and you can still partake in seasonal events that showcase the charm of the area.Ultimately, the best time to visit Oak Lawn for a holiday rental depends on your preference for a vibrant summer experience or a tranquil autumn getaway.
What are the top attractions in Oak Lawn?
In Oak Lawn, visitors can enjoy a range of attractions that highlight the area's charm and community spirit. The Oak Lawn Park District offers a variety of recreational options, including the popular Centennial Park, which features a pond, walking trails, and picnic areas, making it a lovely spot for outdoor activities. Nearby, the Oak Lawn Community High School hosts various events and sports activities, contributing to the local culture.For those interested in history, the Oak Lawn History Museum provides insights into the town's past and showcases local artifacts. Additionally, the area is well-connected to the city of Chicago, allowing for easy day trips to explore iconic attractions such as the Art Institute and Millennium Park. The local dining scene is also worth exploring, with numerous restaurants offering a variety of cuisines that reflect the diverse community.
Are all fees included in the Oak Lawn holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oak Lawn holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oak Lawn with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oak Lawn holiday homes?
You can find great discounts on holiday homes in Oak Lawn on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oak Lawn holiday home booking on Stayz?
To find Oak Lawn holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oak Lawn?
A long-stay holiday home in Oak Lawn is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oak Lawn holiday home?
Book your Oak Lawn holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oak Lawn?
Prices for holiday homes in Oak Lawn vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oak Lawn to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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