
Vacation rentals in Oak Park
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Top-rated vacation rentals in Oak Park
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Park vacation rentals
Other great vacation rentals in Oak Park

Family Friendly Duplex/9 min from MDW/Free Parking
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.

Condo with private terrace, free WIFI and parking
Loved this place! My three friends and I had plenty of space and felt right at home. The location in West Town is perfect -- not busy or loud at all, but very easy to walk to coffee shops or restaurants in less than 10 minutes. Plus, the hosts were very friendly and accommodating!

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16
Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future

Elegant 4Bedroom with Free Parking in Albany Park
Wonderful stay as always, thank you so much!

City Gem: Stylish 3BR for Urban Explorers
Peaceful, felt like home, very spacious and comfortable

Spacious condo with open floor plan and fireplace
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.

Spacious Home in Chicago Suburbs
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.

Home in the Woods!
We had such a wonderful time at Jazmin Airbnb. The place was clean and smell great! She was very responsive and we had no issue with checking into our Airbnb. Thank you for being such a great host!
Quick stats about vacation rentals in Oak Park
Total rentals
320 properties
Total number of reviews
19K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Wifi availability
320 properties include access to wifi
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Oak Park?
Yes! Work meets play with ease at over 180 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in condo rentals in Oak Park?
Experience the best of Oak Park with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Oak Park?
Four-legged friends are welcome in Oak Park. Choose from more than 70 vacation rentals for guests traveling with pets.
Do guesthouse rentals in Oak Park have air conditioning?
Absolutely! We offer over 10 guesthouse rentals with air conditioning in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Oak Park have wireless internet?
Absolutely! We offer over 10 guesthouse rentals with wireless internet in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Oak Park?
Oak Park has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
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