
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.

1920s fully updated unique open artist loft space
True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

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.

Cute, Clean, Cozy Apartment in Pilsen
Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

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.

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at 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.

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.

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 Suite w/Private Entrance Beverly Basement
Great location. recently upgraded. Space: This is a new guest suite in the basement of my home. The suite is equipped with a full kitchen featuring high-quality appliances. The suite includes a large bathroom, a bedroom with a new queen-size mattress, and a washer and dryer onsite. The suite offers a peaceful and comfortable place to stay. A 2 block walk will get you to the commuter train, Subway sandwiches, an Italian deli, CVS Pharmacy, and Starbucks.

Charming Unique 2 Bdrm Apartment in Victorian Home
My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive 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.

Worth It! 3 bedroom ranch home
Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.

Modern Bright 2 Bedroom apartment
This stylish place to stay is perfect for group, family or business trips. High speed internet and a smart TV in each bedroom and the living room should keep you entertained when you are not out and about. Full kitchen in unit including dishwasher and dining table. Outdoor parking on premises. Close to Advocate Christ Medical Center, grocery stores and shopping.
Popular amenities for Oak Lawn holiday rentals
Other great holiday rentals in Oak Lawn

Luxurious townhome 30 days lease open for1-2 weeks

The Blue Room

Comfy Modern Motel Room!

Elegant Beverly Oasis – 20 Mins to Downtown

NEW! Apartment Near Downtown

Midway Airport • 3BR Home • 5 Beds • Free Parking

Safe clean charming close transportation Viva!

Private Spacious Room in a shared house.
When is the best time to visit Oak Lawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £107 | £114 | £104 | £124 | £123 | £129 | £130 | £133 | £124 | £117 | £122 | £118 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
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 100 vacation rentals in Worth, over 50 vacation rentals in Hometown, and over 100 vacation rentals in Chicago Ridge.
How much does it cost to stay in house rentals in Oak Lawn?
Experience the best of Oak Lawn with our house rentals, starting at about $30 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 house rentals in Oak Lawn have air conditioning?
Absolutely! We offer over 20 house 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 £22 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
Destinations to explore
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




