Holiday rentals in Oak Lawn

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Top-rated holiday rentals in Oak Lawn

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A living area showcases an elegant, light-colored sofa paired with a black armchair. A glass coffee table sits atop a patterned rug, while wooden beams accent the ceiling. A dining space can be seen through an archway, complementing the overall spacious feel.
Home in Burbank
4.94 out of 5 average rating, 85 reviews

Spacious-Modern Cozy Home-near Midway-Downtown

Bright and Beautiful home 5 beds 4 baths house located in Burbank, IL , this can be your home away from home. Perfect for vacationers, families, business travelers,free wifi, free private parking, peaceful retreat in desirable neighborhood, ,close to shopping and restaurant 5 miles to Midway airport and 15 miles to downtown and chinatown bring the whole family to this great place with lots of room for fun. Please NOTE : there is * No garage access* * NO PET ALLOWED * *NO SMOKING IN THE HOUSE*

Guest favourite
A spacious living room is highlighted by a sectional sofa adorned with orange and white cushions. A round wooden coffee table complements an accent chair, while a tall plant adds a touch of greenery. Natural light filters through the sheer curtains, enhancing the neutral decor.
Home in Burbank
4.96 out of 5 average rating, 76 reviews

Luxurious House 25 min for downtown

Unwind in style at our stunning Burbank home! With its modern, ultra-cool vibe and sensational light fixtures this house is the perfect retreat after a day of adventures. Conveniently located near Midway Airport✈️ and public transportation 🚍 and just a short Uber ride to downtown Chicago 🌆 you'll enjoy the perfect blend of convenience, comfort, and cool + enjoy free garage and driveway parking for added convenience. 🚗 Come experience the best of Burbank – book now for an unforgettable stay!

Guest favourite
A modern kitchen is presented, featuring stainless-steel appliances including a refrigerator and a gas range. Light wood cabinetry complements the white tiled backsplash, while a mat is placed in front of the sink area, enhancing the functional design.
Flat in Worth
4.88 out of 5 average rating, 26 reviews

Charming 1-Bedroom in Worth, IL

Welcome to your cozy retreat in Worth, IL! This newly remodeled one-bedroom apartment is perfect for a comfortable and convenient stay. Inside, you’ll find a spacious bedroom with a queen bed, fully equipped kitchen with brand-new stainless-steel appliances, an updated bathroom with modern fixtures, and two Smart TVs and highspeed Wi-Fi. Conveniently situated in the South Suburbs of Chicago near shops, parks, and dining, you’ll also have easy access to major highways and public transportation.

Top guest favourite
A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.
Home in Berwyn
4.98 out of 5 average rating, 176 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.88 out of 5 average rating, 161 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favourite
A modern dining area features a large marble table set with plates and utensils, surrounded by upholstered chairs. Pendant lights illuminate the space, highlighting the sleek kitchen in the background, equipped with stainless steel appliances and white cabinetry.
Home in Burbank
4.93 out of 5 average rating, 55 reviews

Cozy getaway in the city.

1 King bed, 1 queen bed, 1 queen sleeper sofa, 1 full and 1 twin bed (bunkbed). 10 minutes from Midway International airport. 2 min from Burbank Park District Water Park. 30 min from downtown Chicago. Close to many stores and shopping centers (Walmart, Target, supermarkets, Costo, Walgreens, etc). 3 milles away from Richard J Daley College. Your family will be close to everything when you stay at this centrally-located place. Very nice and cozy deck and backyard to spend some time.

Top guest favourite
A sitting room features a beige sofa and a cream-colored armchair, positioned near a wooden desk. Two lamps provide soft lighting, while several framed photographs and artwork adorn the walls. Large windows allow natural light to fill the space, complemented by neutral-colored carpeting.
Guest suite in Orland Park
4.97 out of 5 average rating, 112 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

Guest favourite
An open-concept living area is presented with exposed brick walls, a dark blue couch, and a round coffee table. A light-colored accent chair and a small side table provide additional seating. A potted plant adds a touch of greenery beside the couch, enhancing the modern aesthetic.
Flat in Little Village
4.84 out of 5 average rating, 104 reviews

The Chicago Cozy Brick Retreat

This unit offers a charming blend of modern amenities and historic charm. This thoughtfully designed unit features an open-concept living space with exposed brick walls and stylish furnishings. The fully equipped kitchen boasts new appliances, perfect for culinary adventures. The comfortable bedroom, with a cozy bed and ample storage, ensures a restful stay. The sleek bathroom includes contemporary fixtures and a walk-in shower. Street parking is easily available.

Top guest favourite
A polished granite countertop is highlighted, showcasing a vibrant bouquet of pink roses in an elegant vase. Natural light filters through large windows, illuminating a cozy seating area in the background. Decorative greenery adds a touch of warmth to the setting.
Flat in Burbank
4.98 out of 5 average rating, 269 reviews

New & Modern by Midway Airport

Located 4 miles away from Midway Airport in Chicago, Seat Geek Stadium 4 miles away, 20min to Down Town, 15min to Amphitheatre in Tinley Park 2-Bathrooms 3-Bedrooms one with queen size bed and 2 bedrooms with 4 single beds can accommodate up to 6 people. Two TV's 4K Incl. HBO MAX & NETFLIX & PEACOCK. Whether you're in town on business or for personal reasons our space has been meticulously designed to provide you with the best stay in the area! Digital check-in.

Guest favourite
A spacious bedroom features a large bed with a dark blue duvet and an orange-accented blanket. Two nightstands with lamps are positioned on either side, and colorful artwork decorates the walls. Natural light enters through a window, framed by soft, light pink curtains.
Home in Worth
4.85 out of 5 average rating, 157 reviews

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.

Guest favourite
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.91 out of 5 average rating, 170 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Guest favourite
A bright living area features a spacious sectional sofa arranged around a coffee table. Natural light enters through large glass doors, complemented by sheer curtains. A dining table with woven chairs and a television adds to the inviting atmosphere.
Apartment in Chicago Ridge
5 out of 5 average rating, 14 reviews

Quintessential vibes 2Br/2Bath

Quintessential vibes is freshly renovated with brand new flooring, freshly painted and styled with comfort. Whether it’s a work trip, family visit or a simple vacation/getaway comfort and relaxation will accommodate all. Unit is located on third floor with no elevator. Free assigned parking. One right outside the building and one in building garage. This stylish place to stay is perfect for group trips.

Popular amenities for Oak Lawn holiday rentals

When is the best time to visit Oak Lawn?

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Avg. price$187 SGD$200 SGD$182 SGD$218 SGD$216 SGD$226 SGD$227 SGD$232 SGD$217 SGD$205 SGD$214 SGD$208 SGD
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Frequently Asked Questions

  • Where should I stay in Oak Lawn?

    Make yourself at home in Oak Lawn by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Hometown, over 100 vacation rentals in Chicago Ridge, and over 100 vacation rentals in Worth.

  • How much does it cost to stay in apartment rentals in Oak Lawn?

    Experience the best of Oak Lawn with our apartment rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Oak Lawn?

    Yes! Work meets play with ease at over 10 house rentals in Oak Lawn featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do condo rentals in Oak Lawn have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Oak Lawn. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Oak Lawn?

    Oak Lawn has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Oak Lawn have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning in Oak Lawn. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Oak Lawn?

    Four-legged friends are welcome in Oak Lawn. Choose from more than 10 house rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Oak Lawn?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Oak Lawn

  • Total holiday rentals

    Explore 40 holiday rentals in Oak Lawn

  • Nightly prices starting at

    Oak Lawn holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,340 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Oak Lawn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Oak Lawn rentals

  • 4.7 Average rating

    Oak Lawn stays receive an average rating of 4.7 out of 5 from guests

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