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Holiday houses in Chicago Ridge

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Top-rated holiday rentals in Chicago Ridge

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

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Condo in Hickory Hills

4.91 out of 5 average rating, 58 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.

16–23 Dec

$179 NZD per night

Guest favourite

Condo in Palos Hills

4.84 out of 5 average rating, 166 reviews

~Home Comforts, Roku SmartTV, Fast WiFi~

Enjoy the comforts of home in this first floor, private 2-bedroom condo in the SW Chicago Suburbs. We offer all the amenities you need. There are two queen beds, plus a full-size futon, full-size sofabed, and a very comfy couch your sleeping comfort. Enjoy the luxury of hotel quality sheets and plush towels, plus lots of pillows and blankets. We are near Moraine Valley Community College, Stagg High School, Palos Community Hospital, many forest preserves & trails, golf courses, and much more...

27 May – 3 Jun

$294 NZD per night

Guest favourite

Campervan/RV in Willow Springs

4.98 out of 5 average rating, 40 reviews

Wander Willow Springs Glamping Retreat

Nestled in the serene landscapes of Willow Springs, the Wander Willow Springs RV offers a peaceful and immersive getaway. Relax in a cozy, fully-equipped stationary RV. Unwind in nature's embrace, just 1 block from Chicagoland's largest forest preserve. Immerse yourself in the tranquility of your surroundings while savoring a cup of coffee on the outdoor patio w/fire pit, explore the forest's miles of hiking and biking trails or the village's charm from the comfort of your own private retreat

23–30 Mar

$194 NZD per night

Guest favourite

Guest suite in Orland Park

4.99 out of 5 average rating, 70 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.

25 May – 1 Jun

$219 NZD per night

Guest favourite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 237 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

19–26 Nov

$218 NZD per night

Guest favourite

Home in Worth

4.87 out of 5 average rating, 100 reviews

The Comfy King Ranch/ King Bed/Disney+ /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.

24–31 Jan

$520 NZD per night

Guest favourite

Apartment in Cicero

4.98 out of 5 average rating, 200 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.

11–18 Nov

$240 NZD per night

Guest favourite

Apartment in Blue Island

4.93 out of 5 average rating, 262 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.

12–19 Jun

$252 NZD per night

Guest favourite

Home in Chicago Ridge

4.89 out of 5 average rating, 47 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.

18–25 Mar

$260 NZD per night

Home in Whiting

4.8 out of 5 average rating, 225 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

19–26 Feb

$204 NZD per night

Guest favourite

Condo in Chicago Ridge

4.96 out of 5 average rating, 56 reviews

Industrial Sheek Gem

Discover urban living at its best in this renovated, spacious condo. Set in a charming 5-unit building, it seamlessly blends luxury with practicality, featuring a private garage, in-unit laundry, and a balcony. Enjoy serenity while staying connected to the vibrant city. Welcome to a lifestyle where sophistication meets convenience and tranquility meets connectivity!

21–28 Nov

$347 NZD per night

Guest favourite

Home in Justice

4.95 out of 5 average rating, 191 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.

24–31 Dec

$1,109 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chicago Ridge holiday rentals

Free parking on premises

Air conditioning

Stay near Chicago Ridge's top sights

Chicago Ridge Mall21 locals recommend

AMC Chicago Ridge 64 locals recommend

Jenny's Steak and Banquets4 locals recommend

Other great holiday rentals in Chicago Ridge

Guest favourite

Home in Chicago

4.92 out of 5 average rating, 85 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

29 Dec – 5 Jan

$255 NZD per night

Home in Palos Hills

4.91 out of 5 average rating, 11 reviews

Cozy lower level in Palos Hills

1–8 Jan

$284 NZD per night

Guest favourite

Condo in Evergreen Park

4.8 out of 5 average rating, 91 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

28 Oct – 4 Nov

$252 NZD per night

Guest favourite

Apartment in Lemont

4.96 out of 5 average rating, 23 reviews

Burr Oak

9–16 Aug

$138 NZD per night

Guest favourite

Home in Robbins

4.97 out of 5 average rating, 36 reviews

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

22–29 Sep

$235 NZD per night

Guest favourite

Apartment in Homewood

5.0 out of 5 average rating, 39 reviews

Charming Garden Apartment

5–12 Feb

$213 NZD per night

Guest favourite

Home in Berwyn

5.0 out of 5 average rating, 73 reviews

Retro Modern Bungalow | free parking | pets ok

1–8 Dec

$262 NZD per night

Guest favourite

Apartment in Lyons

5.0 out of 5 average rating, 15 reviews

Beautiful & Private, 1bdrm, 1bath w/washer & dryer

15–22 Aug

$217 NZD per night

Destinations to explore