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Compare 503 Vacation Homes in Chicago Ridge with updated reviews, rates, and availability.

Belmont House, Classy & Chic/walk to Wrigley Field
Interior

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (41)
"Perfect location. Home was very comfortable and inviting. Beds and mattresses were heavenly. We thoroughly enjoyed our stay. "
Belmont House, Classy & Chic/walk to Wrigley Field
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Interior

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stunning / Spacious 6BD Home + garage - Bucktown!
Private kitchen

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!
Cheery 2+bedroom home with free parking on premises
Living area

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"My husband and I spent a week here with our three dogs while in town for a family wedding. I was able to work from home while my husband took the CTA into the Chicago office of his company. The home was lovely and well stocked with everything that we needed for a week away from home. Would highly recommend."
Cheery 2+bedroom home with free parking on premises
Eddy House, Roscoe Village Hideaway
Living area

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway
Woodlawn Oasis...10 Minutes to Dining & Downtown
Living area

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown
Luxury Home Away From Your Home
Exterior

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Interior

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (35)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Lincoln Park Living - 3 Queen Beds - Sleeps 6!
Living Room

Lincoln Park Living - 3 Queen Beds - Sleeps 6!

9.6 out of 10, Exceptional, (9)
"We needed a place to sleep with our 3 young adult sons over the Christmas holiday and this place was perfect for that. It is very basic, but also much less expensive than most other places in this area, and in an excellent location. There are 2 coffee shops just around the corner and plenty of restaurants within easy walking distance. The rooms are clean and spacious. The bedroom has blackout curtains and comfortable beds. Seeing that it is located on a fairly busy street, the apartment was very...
Lincoln Park Living - 3 Queen Beds - Sleeps 6!
Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (17)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Lincoln Park Living - Suite 2!
Living Room / Dining Room

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (22)
"The property was exactly as advertised. Great location for our weekend visit. Very comfortable and had everything we needed for a 2 night stay. "
Lincoln Park Living - Suite 2!
Cozy 5-bedroom with lake views and spacious deck
Outdoor dining

Cozy 5-bedroom with lake views and spacious deck

10.0 out of 10, Exceptional, (8)
"This was our 2nd year in a row staying here. Everything was great yet again. I highly recommend this house for anyone staying in the area."
Cozy 5-bedroom with lake views and spacious deck
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
New sectional sofa from Arhaus.

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (88)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Full Luxurious Modern House Near Chicago
Living area

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Matteson Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | Stairs Required

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Dining

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

9.8 out of 10, Exceptional, (20)
"This place has plenty of beds and is on walking distance to everything you might need. Parking is free. Would stay again. "
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.
Exterior

Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.

10.0 out of 10, Exceptional, (8)
"Great location in a safe neighborhood close to lots of bars and restaurants."
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
BEAUTIFUL 4-story home located in one of Chicago’s safest neighborhoods!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

9.6 out of 10, Exceptional, (5)
"Our group consisted of 8 people ranging from preteens to octogenarians and we all really enjoyed this townhome! It was attractive, clean, updated and stylish, yet retained some of the historic ambiance of the neighborhood. Beds were comfy. Bedrooms are attractively decorated. Kitchen was roomy and easy to work in. Aga stove was a new experience, but after a short learning curve, we mastered it. The youngest members claimed the top floor as their space, which worked well. The home is a short walk...
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
The Grand Kimball Lodge, Logan Square, Sleeps 14
Make yourself at home, great space to hangout and create good memories.

The Grand Kimball Lodge, Logan Square, Sleeps 14

10.0 out of 10, Exceptional, (1)
The Grand Kimball Lodge, Logan Square, Sleeps 14
858 Orleans
Terrace/patio

858 Orleans

3.0 star property
858 Orleans
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chicago Ridge

Sentral Michigan Avenue
Garden

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (649)
"Was very different and unique "
The price is SAR 412
SAR 593 total
includes taxes & fees
22 Jan - 23 Jan
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
Front of property

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (348)
"The property was very clean, it had everything we needed, the communication was excellent prior and during our stay. I will be recommending to others. "
Kasa Magnificent Mile Chicago
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (412)
"Beautiful Hotel with lots of amenities and entertainment in a walking distance "
The price is SAR 376
SAR 441 total
includes taxes & fees
30 Jan - 31 Jan
Sonder South Wabash
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.