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Holiday houses 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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Condo in Hickory Hills

4.92 out of 5 average rating, 60 reviews

Convenient Location near ammenities. KING size bed

Walking distance to restaurants, stores etc. 1st floor suite will be your relaxing retreat. King size bed with a foam mattress, down pillow/comforter set, blackout curtains will allow you a restful sleep. BR is equipped with 2 side tables, 2 dimmable touch control table lamps with 2 USB Ports & AC Outlet. Bath offers a tub, vanity & open shelving. LR features faux leather sofa, coffee table w/the lift-top & 70” streaming TV. LR opens up to an eat in kitchen equipped with standard dine-ware.

20 – 27 Sept

$1,131 AUD total

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 88 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.

5 – 12 Dec

$1,597 AUD total

Guest favourite

Loft in Chicago

4.94 out of 5 average rating, 158 reviews

Entire Spacious, Private Loft Apt Historic Beverly

You have the loft suite to yourself. Best for 1 - 2 people Access through the front door & complete privacy with a bathroom and separate entrance (locked door). in a victorian farmhouse in lovely, tree-lined historic Beverly. Cozy and safe and well stocked with beverages & snacks. We are onsite hosts as we live on the 1st two floors of the house. NOT SUITABLE for those who have difficulty with stairs (3rd floor) Queen bed and twin daybed available Free street parking

8 – 15 May

$1,398 AUD total

Guest favourite

Guest suite in Orland Park

4.99 out of 5 average rating, 72 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.

23 – 30 May

$1,437 AUD total

Guest favourite

Apartment in Oak Lawn

4.95 out of 5 average rating, 123 reviews

Charming One Bedroom Apartment

Enjoy your stay in Oak Lawn in this modern and rustic, newly remodeled one-bedroom apartment! It is conveniently located right by Christ Hospital, Metra station and Midway Airport. The apartment is comfortable for up to 4 people, has a private bedroom and a pull out sofa in the living room. You will have a full kitchen, work space, entertainment area with TV and a comfy bed for your best night rest. There is Wifi, Netflix, hulu, and YouTube TV.

11 – 18 July

$1,652 AUD total

Guest favourite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 242 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

7 – 14 Mar

$1,356 AUD total

Guest favourite

Apartment in Cicero

4.98 out of 5 average rating, 202 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

23 – 30 Apr

$1,603 AUD total

Guest favourite

Apartment in Forest Park

5.0 out of 5 average rating, 222 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

24 – 31 Oct

$1,391 AUD total

Guest favourite

Apartment in Blue Island

4.93 out of 5 average rating, 265 reviews

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.

24 – 31 Dec

$1,597 AUD total

Guest favourite

Guest suite in Wheaton

4.85 out of 5 average rating, 103 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

28 Dec – 4 Jan

$1,291 AUD total

Guest favourite

Home in Chicago Ridge

4.9 out of 5 average rating, 52 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.

2 – 9 Oct

$1,748 AUD total

Guest favourite

Home in Justice

4.95 out of 5 average rating, 193 reviews

3 Kng|1 Qn|1 Full|3AirBds|Basketball Crt|FreePark

3 Kings | 1 Queen | 1 Full | 3 air beds | 2 Pack 'n Plays No charge for cleaning, extra people, or any other hidden fees. 20% weekly discount applied to 7+ nights. Minutes to I-294, I-55. 30 mins to Chicago & O'Hare Airport. 20 mins to Midway Airport. 5 mins to Cook County’s forest preserves w/ bike, walking, and horse trails.

29 Sept – 6 Oct

$6,056 AUD total

Holiday rentals for every style

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Popular amenities for Oak Lawn holiday rentals

Free parking on premises

Air conditioning

Stay near Oak Lawn's top sights

Chicago Ridge Mall21 locals recommend

Portillo's Hot Dogs10 locals recommend

Advocate Christ Medical Center4 locals recommend

Jewel-Osco9 locals recommend

Cooper's Hawk Winery & Restaurant10 locals recommend

STACKED - Oak Lawn4 locals recommend

Other great holiday rentals in Oak Lawn

Apartment in Oak Lawn

4.83 out of 5 average rating, 24 reviews

Lovely & Modern 2 Bd Apt near Golf Course

3 – 10 Sept

$2,132 AUD total

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 37 reviews

Ultra Modern Beverly Suite

21 – 28 Dec

$1,632 AUD total

Guest favourite

Home in Worth

4.96 out of 5 average rating, 45 reviews

Luxurious & Modern Cozy House in Chicago Suburb!

18 – 25 Nov

$2,446 AUD total

Guest favourite

Home in Palos Hills

4.92 out of 5 average rating, 12 reviews

Cozy lower level in Palos Hills

23 – 30 Nov

$1,861 AUD total

Condo in Evergreen Park

4.8 out of 5 average rating, 92 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

3 – 10 Oct

$1,565 AUD total

Guest favourite

Campervan/RV in Willow Springs

4.98 out of 5 average rating, 44 reviews

Wander Willow Springs Glamping Retreat

30 Mar – 6 Apr

$1,186 AUD total

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 12 reviews

Beverly Cottage Loft

12 – 19 Dec

$1,653 AUD total

Guest favourite

Home in Robbins

4.97 out of 5 average rating, 37 reviews

Comfy Updated 3 Bdrm/2Bth -Near SXU, MVC & MDW

24 Sept – 1 Oct

$1,447 AUD total

Quick stats about holiday rentals in Oak Lawn

Total rentals
40 properties
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
940 reviews

Destinations to explore