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Compare 572 Vacation Homes in Oak 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, (86)
"Location of house is great, communication with owner is great. The house "
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

Your Next Vacation Home

9.8 out of 10, Exceptional, (31)
"It was great! close to a lot. "
The price is AED 551
AED 1,031 total
includes taxes & fees
2 Mar - 3 Mar
Your Next Vacation Home

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (48)
"Enjoyed our stay. Lots of common areas to work remotely and to socialize."
Breathtaking home close to Schaumburg, Chicago

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

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (52)
"This property was in a great location! Easy to find and central to make getting to the surrounding cities super easy. The property was easy to access, which was my number one worry, and we had a fantastic time with our stay. Thank you, Amanda!"
Spacious open concept home w/ game room + firepit

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (73)
"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (39)
"We stayed here in January to visit some family and enjoy the city. The location of this place is amazing. its right downtown , very walkable to everything. The parking is great, with the 2 car garage it was heaven for being in the city. The property is so nice. Its massive. upstairs and downstairs ; with room for so many people. We ended up only have four people ; and just loved it. The living room is so cozy, with the fireplace and sofas, the property was perfect. Matches all the...
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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

"The house was suitable for our team of 9 that was in Chicago for a training. The location was close to downtown, but parking in front of the house was impossible - the street was full for blocks. The alley spot was small and we had to do multiple moves to get one vehicle into the concrete pad. There was no option to park in the garage as garbage cans and piles of garbage were in front of the door. One of the upstairs bathrooms had a tub that would hardly drain and the other had a handle that...
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

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

9.6 out of 10, Exceptional, (7)
"Stayed here for a week while attending a festival and central downtown location was good. Having the garage was very helpful but suggest you have a small car as the garages are very shallow. Common area with kitchen and TV is very spacious for lounging"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Berwyn Beauty

10.0 out of 10, Exceptional, (13)
"Amazing... location, price, amenities, etc."
Berwyn Beauty

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

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

4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

9.4 out of 10, Exceptional, (8)
"Excellent home, plenty of room, very clean."
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

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!

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (38)
"Numerous problems that owner tried to fix-no wi-fi, no ac, broken upstairs dishwasher, basement flooded when we used downstairs washing machine. Place had not been cleaned prior to check in, trash sack in entry way, litter on floor, mop on back steps. Great location."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (123)
"Spacious inside, 9 bedrooms, very warm in a cold month. Good location to walk, close to public transit and ample parking - squeezed in 5 vehicles. Owner contact and responses excellent."
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
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 Oak Park

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (102)
"Stayed with my husband and our two preteens. I grew up in Oak Park and chose this based off of location and it was perfect. Walkable neighborhood, close to the El and downtown Oak Park. The house was clean and comfortable, on top of having the quintessential Oak Park / Chicago vibe Communication was easy so was check in and out. I would choose to stay here again for sure!"
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (36)
"I texted the host a question and he almost immediately got back to me and talked me through the entire check-in process, and he didn’t hang up until he was sure we were able to get in! This was my first out-of-state trip with my boyfriend, so it was an enormous relief to have such a dedicated host to help us out! Additionally, the interior was tidy and very pleasantly decorated!"
The price is AED 193
AED 584 total
includes taxes & fees
24 Feb - 25 Feb
Chic Suite/Mins to L Train /Laundry/Free Parking

Oak Park Queen

9.4 out of 10, Exceptional, (12)
"Wonderful place. Stayed four nights and went in and out to visit family in Oak Park and nearby neighborhoods. Everything you will need when looking for a place to stay. Clean, roomy, comfy and had everything we needed!Consider staying here!"
The price is AED 422
AED 853 total
includes taxes & fees
24 Feb - 25 Feb
Oak Park Queen
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.