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Compare 435 Vacation Homes in Calumet Park with updated reviews, rates, and availability.

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

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

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

9.4 out of 10, Exceptional, (85)
"We rented this house so that two families could stay for the weekend in Chicago to celebrate our kids engagement. The house is great, it's pet friendly, it's in a great location, the garage is very useful for parking cars, etc. However, you really, really need to read the owner's rules. If you read the listing's first part "great place for your friends and family gathering", "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (1)
"Awesome stay!"
The price is SAR 484
SAR 1,190 total
includes taxes & fees
24 Jan - 25 Jan
Spacious 3br home near Chicago, fenced yard for pets

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Entire house 1 city block from Wrigley Field.

9.8 out of 10, Exceptional, (19)
"Very comfortable home close to Wrigley and to restaurants, coffee shop and shopping."
Entire house 1 city block from Wrigley Field.

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

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (36)
"First of all, this property was sooooo easy to travel to. I dont mind city driving, but I do get nervous driving downtown. It was so SIMPLE, literally fool proof!! Conveniently located a few blocks from 41 made for a stress-free 15 minute drive to Shedd Aquarium.The house is absolutely beautiful and in a great neighborhood. The property was very secure, neighbors were friendly, and tons of great places within walking distance. Gorgeous original architecture, built ins and stained glass. The...
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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

9.8 out of 10, Exceptional, (6)
"Great location so convenient to everything! Great to have a garage to park. Also, great to have the 2 bedrooms with their own bathrooms! Property met our needs. It was not dirty but was not as clean as it could have been. (Mainly the floors) Overall the house worked great for us! "
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Berwyn Beauty

10.0 out of 10, Exceptional, (12)
"Perfect for visiting family by with more space than an hotel. A nice neighborhood. Away from the hustle and bustle of downtown but an easy drive for vacationers. "
Berwyn Beauty

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

LUXE 3 BR, 2 BA + Hot Tub

9.0 out of 10, Wonderful, (20)
"Everything was nice and cleaned.Will stay again "
The price is SAR 563
SAR 1,175 total
includes taxes & fees
26 Jan - 27 Jan
LUXE 3 BR, 2 BA + Hot Tub

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (45)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is SAR 608
SAR 1,334 total
includes taxes & fees
23 Feb - 24 Feb
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"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!

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

Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

10.0 out of 10, Exceptional, (33)
"We had a terrific stay at here. The apartment was sparkly clean. The linens were like new. The bed was comfortable and cozy. It’s a basement apartment but you don’t feel “underground” at all. It’s light and airy, laid out well with plenty of living space. It’s on a quiet residential block and conveniently located for public transportation and walking to restaurants. Caitlin checked in with us just the right amount—to be sure the temperature was right (it was) and if we needed anything (we...
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (44)
"Fantastic house…whole family enjoyed our stay. Thank you!"
Luxury House in the heart of Old Town with Parking
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 Calumet Park

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (661)
"We stayed at Sentral after a trip to the Shedd with the kids. We had a great day and evening in the city and when we finally got to our room, we couldn't believe it! It was so spacious, we could have stayed for a week. Full kitchen, stocked with appliances, utensils, plates and glasses. Two full baths, two bedrooms and more closet space than we could have possibly used. Location was close to everything you'd need. We'll definitely be back."
The price is SAR 411
SAR 593 total
includes taxes & fees
27 Jan - 28 Jan
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (419)
"Great place to spend a few days. "
The price is SAR 412
SAR 484 total
includes taxes & fees
28 Jan - 29 Jan
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (243)
"New. Modern. Cozy.Clean & quiet place. Will book it again!"
The price is SAR 230
SAR 269 total
includes taxes & fees
17 Feb - 18 Feb
Sonder Market Hall
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.