Search Vacation Homes in Oak Park

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 746 Vacation Homes in Oak Park with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (27)
"The neighborhood was very cute, but parking was an issue. We also realized the second day that the windows in the front room were not locked, and one of them was open. The curtains had them covered so we didn’t think to check the first night in. Also, i think the vacant apartment upstairs was being actively shown, so when we were at the property, there were several different folks coming in and out. Overall, it was comfy for the two nights we stayed."
Great 3 bedroom rental unit near Logan Square

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

10.0 out of 10, Exceptional, (164)
"We stayed here for my sister’s bachelorette. Location was great and the space was huge, perfect for our big group."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

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

10.0 out of 10, Exceptional, (7)
"Clean and in a nice neighborhood "
Cozy 3-bedroom house in family-oriented Melrose Park.

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (101)
"My friends and I had a wonderful stay at this property. It is very cute and conveniently located in a nice neighborhood (Oak Park/Forest Park areas) with easy access to 290 that takes you straight to the heart of downtown Chicago. The house had many amenities and you can tell the hosts are very considerate/thoughtful. Would highly recommend! "
Updated Forest Park 3 BR Bungalow

Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

10.0 out of 10, Exceptional, (2)
"This is a very beautiful and amazing place. Great for family stay or group . Clean house , everything listed online is exactly as it is. Food and malls nearby. Overall great accommodation. Will definitely visit again anytime I’m in Chicago. Thank you !"
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

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

9.2 out of 10, Wonderful, (90)
"The space was perfect for multiple families who want to stay in a great neighborhood, close to the train, shopping, restaurants bars and more. Worked out perfectly for a few friends and their kids with plenty of space for sleeping and hanging out. Even had 2 spaces for cars in a garage!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (14)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (163)
"everything about this house was wonderful. The beds were comfortable. Everything was clean. The family had a lot of fun. We were able to invite other family members over to visit. My daughter loved playing the piano, just made the mini family reunion perfect. Thank you for sharing your amazing home."
Historic home with easy access to Chicago

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.6 out of 10, Exceptional, (11)
"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

3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl

3.0 star property
9.8 out of 10, Exceptional, (27)
"Can’t get a better location if you want to be near wrigley! Nicole was great to deal with and we loved it. Will be back."
3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl

2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

9.2 out of 10, Wonderful, (17)
"We had a great stay."
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

Berwyn Beauty

10.0 out of 10, Exceptional, (15)
"We had an amazing time at the Berwyn Beauty. Good location and response time to messages! We Came down for Americas Beauty show and had the most amazing time. "
Berwyn Beauty

BoHo House - A Chic, 1903 Chicago Workers Cottage

10.0 out of 10, Exceptional, (10)
"Well located, comfortable and stylish home. The backyard was great to let the dog out and would be a fabulous place to hang out in warmer weather. Perfectly clean throughout, and great host communication made for a wonderful stay."
BoHo House - A Chic, 1903 Chicago Workers Cottage

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, (23)
"This property was is in a good neighborhood nice and clean I really enjoy myself Thanks"
The price is SAR 845
SAR 1,498 total
includes taxes & fees
13 Apr - 14 Apr
LUXE 3 BR, 2 BA + Hot Tub

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (2)
"This was a great rental experience from start to finish. Everyone was impressed with the space, and the location couldn't be better. We will definitely be back. "
Spacious 5-bedroom house with movie room, game room and more!

House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar

Spacious and Sleek 4BD/2.5BA - Logan Square!

9.4 out of 10, Exceptional, (18)
"Overall, we had a great time in Chicago. The area was perfect and it’s located right across a school so it made it a bit more entertaining when seating out in the balcony. The home had all we looked for and was very much pretty clean. Nice place to stay and will definitely reconsider for our next stay. "
Spacious and Sleek 4BD/2.5BA - Logan Square!

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

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

9.6 out of 10, Exceptional, (18)
"Well-stocked kitchen, towels and cleaning supplies. Hostess seemed to go the extra mile to help us feel welcomed with water, soda, coffee options and candy. Just slight confusion and panic on our part when they had our arrival date not until the next day, but it was remedied and all was well. "
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
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.
Don't see what you're looking for?
See all available properties in Oak Park
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Oak Park

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

9.6 out of 10, Exceptional, (39)
"This was the perfect place for my boyfriend and I to stay for our little 48 hour trip. Every thing was perfectly explained in detail and that helped so much because we got there later at night. It is right outside the city and has great options located all around as well. I will recommend this place to anyone traveling to the Chicago area. "
The price is SAR 307
SAR 720 total
includes taxes & fees
21 Apr - 22 Apr
Chic Suite/Mins to L Train /Laundry/Free Parking

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (56)
"My husband, daughter and I went to Chicago for a weekend getaway and this place was clean, cute and so close to transit. Great place for a small family to stay. "
The price is SAR 450
SAR 1,039 total
includes taxes & fees
13 Apr - 14 Apr
Cozy, Comfortable and Convenient apartment. Close to everything!

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (726)
"Great family place to stay. "
The price is SAR 412
SAR 593 total
includes taxes & fees
13 Apr - 14 Apr
Sentral Michigan Avenue
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.