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Compare Vacation Homes in Countryside with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (25)
"The property is as described and was perfect for our stay. David answered all of our questions promptly. Would definitely recommend this host and property."
Great 3 bedroom rental unit near Logan Square

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (87)
"Spacious property. Plenty of room and great neighborhood. Wish the larger TV was upstairs. "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.6 out of 10, Exceptional, (8)
"The house is located in a neighborhood that is easily walkable and has anything you need within walking distance. Metro is located within a few blocks of the house and makes getting around easy."
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (19)
"This was perfect for our needs. Great location, comfortable and clean. I'm sure we'll be back."
Cozy Home Sweet Homewood.

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (5)
"We stayed on Valentine's weekend. Used the fireplace and the hot tub as these were must haves for us. Everything was very clean, so I felt a little bad dirtying the fireplace up. The owner was super responsive and accommodating. Would definitely consider staying again if we find ourselves in that area again."
Cozy 3-bedroom house in family-oriented Melrose Park.

Your Next Vacation Home

9.6 out of 10, Exceptional, (35)
"Very clean and tidy. We didn't stay long, just slept overnight before heading out again, but the rooms were comfortable."
The price is SAR 694
SAR 1,186 total
includes taxes & fees
13 Apr - 14 Apr
Your Next Vacation Home

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

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

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (22)
"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"
The price is SAR 844
SAR 1,496 total
includes taxes & fees
17 Mar - 18 Mar
LUXE 3 BR, 2 BA + Hot Tub

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (13)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (31)
"Location is great, size of the house is great with queen beds in all room and even one with a King bed. Basement was very cold, ( it’s winter) so that bedroom was not used but wasn’t needed anyways. The house needs a really good cleaning especially the kitchen especially the cabinets. Also coffee maker is tiny, doesn’t make sense considering the size of the house. Ironing board had no cover just metal frame, kitchen was not stocked properly for the size of the house. Loved the fact there was...
Stunning / Spacious 6BD Home + garage - Bucktown!

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (10)
"House was clean and the check in process was easy. The gated driveway easily fit 3 cars with room to spare."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

8.8 out of 10, Excellent, (8)
"The house was very nice. Great neighborhood."
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

9.8 out of 10, Exceptional, (73)
"We spent a wonderful long weekend enjoying the surrounding area. Plenty of shops, bars and restaurants within easy walking distance. The host was very good with communicating, unit was very spacious and clean. Perfect place to stay in Wrigleyville"
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (99)
"My friend and I used this property as home base for a weekend trip to Chicago. The green line is a 5 minute walk, and then 30 minute ride to downtown. We also stopped at the conservatory which was wonderful.The Frank Lloyd Wright house is a 20 minute walk. We ate at several restaurants within walking distance. Citrine was our favorite and the Broken Tart for coffee and cake.The house was very comfortable and well stocked. It is very clean. All the bedrooms are off street side, and very...
Updated Forest Park 3 BR Bungalow

Private Home Awaits

The price is SAR 675
SAR 1,636 total
includes taxes & fees
16 Mar - 17 Mar
Private Home Awaits

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.8 out of 10, Exceptional, (84)
"The location near Old Town was perfect walking distance from Second City and many bars and restaurants. We chose this unit not only for the location but also because the arrangement of the rooms with double queen beds was very convenient for my guests with kids. The kitchen was well stocked and though the living room was a little smaller, there was plenty of room for everyone to spread out. The beds were comfortable. The one thing to note is that the extra family room space on the third floor...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.0 out of 10, Wonderful, (7)
"To say we enjoyed our stay, is an understatement. My sister was able you bring in her 21st birthday properly along with her close friends. It was so spacious, everyone had their own area to hang out. The master bedroom is gorgeous, a real selling point. My only regret is that it is winter && we were unable to enjoy the backyard. Our host was amazing and very helpful during the whole process, any question was promptly answered. If you’re looking for a nice place in a quiet area, don’t hesitate to...
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (52)
"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
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 Countryside

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (699)
"Friendly staff "
The price is SAR 475
SAR 668 total
includes taxes & fees
23 Mar - 24 Mar
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (448)
"A great stay! I’d definitely come back."
The price is SAR 371
SAR 435 total
includes taxes & fees
27 Mar - 28 Mar
Sonder South Wabash

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (148)
"Amazing place to go relax and get peace. Definitely a must "
The price is SAR 471
SAR 553 total
includes taxes & fees
25 Mar - 26 Mar
Sonder The Burnham Apartments
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.