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Condo holiday rentals in Oak Park

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Popular amenities for Oak Park condo rentals

Weekly condo rentals

Guest favourite
Condo in Humboldt Park
4.93 out of 5 average rating, 68 reviews

Urban Oasis Getaway. 6 stops to downtown!

LydiaRating, 5 stars2 weeks ago
The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!
Guest favourite
Condo in Forest Park
4.92 out of 5 average rating, 25 reviews

Lovely, Pet Friendly Condo w/ King Bed & Parking!

MollieRating, 5 stars3 weeks ago
We had such a fun weekend staying at this unique and charming property! The place itself had tons of character. It’s in a great location—just minutes from a bunch of fantastic restaurants and only a short drive to the Brookfield Zoo. We also took a quick trip into the city to visit the Shedd Aquarium, and it couldn’t have been easier. The location really strikes the perfect balance between relaxing and convenient.
Top Guest favourite
Condo in East Rogers Park
4.98 out of 5 average rating, 109 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

CarolRating, 5 stars1 week ago
The condo is in a quiet and attractive neighborhood and the hosts answered my few questions promptly. The place was very clean and although the bedrooms were small, it was nice that each of us (nana and two teens) could have their own space.
Superhost
Condo in Stickney
4.91 out of 5 average rating, 23 reviews

2BR Chicago Escape | 20 min DT, Parking, Laundry

SilviuRating, 5 stars1 week ago
Very nice place, the host help us with the details, we had an issue with the washing room, door was locked by wind or another person, and we had support to find the key for that room!
Superhost
Condo in Garfield Ridge
4.84 out of 5 average rating, 19 reviews

1st Floor Condo Apartment Close to Midway Airport

SharliamarRating, 5 stars5 days ago
We enjoyed our stay here. We felt safe and the home was very clean. The kitchen had everything you need if you desire to cook at home. Our host was very accommodating us and allowing us to check in earlier which was extremely helpful! We will definitely come back again!
Top Guest favourite
Condo in Near West Side
5 out of 5 average rating, 29 reviews

Quick Drive to Downtown Chicago & Early Check-In

RoopaRating, 5 stars1 week ago
Thomas is an amazing host! He was very proactive in communicating right from the start of the trip ,was very welcoming and warm. This Airbnb house is spic and span. It is very clean , beautifully decorated and has everything you need to be comfortable in a home. The Kitchen is stocked with all vessels , has basic pantry supplies and has a gas for cooking warm meals. Thomas and his wife were also very thoughtful and considerate and left us a basket full of snacks and coffee pods - that was a really sweet gesture from their end.The coat closet has umbrellas , incase you need one , which I thought was very considerate as well. Thomas also regularly checked in on us to ensure we had a smooth stay - his check in and checkout instructions were uber clear and made it possible to check in and check out without any hassles. There is a starbucks and a bunch of small restaurants on a 10 - 13 min walk from the house.Overall , I would highly recommend his house to other guests.
Superhost
Condo in Elmwood Park
4.63 out of 5 average rating, 16 reviews

Top Floor Condo near airport

KimberlyRating, 5 stars6 days ago
We stayed 3 days and felt very safe in the area and condo was as described. I was worried about street parking; but never had a problem finding a space nearby. No one bothered us or our car. This is a nice, quiet, walkable neighborhood. Restaurants and shopping nearby. If you want to use the train, it is nearby as is the airport. There is also easy access into the city by car. You do hear the train and sometimes planes, but it's not too bad. This place was clean and comfortable. There were plenty of pots, pans, and dishes so you could cook a full meal if needed. Mixed review on beds. I like a firm mattress and was 100% comfortable in the Queen, I slept better than I do at home! My daughter and son in law did not like the King, but they use a very soft mattress with an additional soft topper at home. The air mattress was ok, but my Granddaughter preferred the couch. If I ever return, I would stay here again. Overall, this was excellent and priced fairly.
Superhost
Condo in Chicago
5 out of 5 average rating, 13 reviews

Bronzeville Oasis

MicheleRating, 5 stars3 weeks ago
recently had the pleasure of staying at Carlton's Airbnb in Chicago with family - 4 adults. We couldn't be more satisfied with my experience. From the moment we arrived, we were impressed by the cleanliness and attention to detail throughout the property. The decor was absolutely beautiful, creating a warm and inviting atmosphere that made me feel right at home. The beds were comfortable. Additionally, the convenience of parking was a huge plus, making it easy to come and go without any hassle. Overall, this Airbnb met my expectations in every way. I would definitely stay here again and highly recommend it to anyone looking for a comfortable and stylish place to stay in Chicago.

Pet-friendly condo rentals

Superhost
Condo in Lincoln Park
4.83 out of 5 average rating, 363 reviews

Chic and Charming Vintage Condominium in Lincoln Park

FojanRating, 5 stars2 days ago
We enjoyed our stay! First and foremost Colin was superb! Very responsive and respectful. Many pros about the place: loved the bright bedroom, walkable to many restaurants, neighborhood felt safe, we did not travel with young kids but kids bedroom could have been fun for young kids, the parking spot provided was a huge plus. cons were loud AC, mattress was not as comfortable as one would hope. Place could use some simple aesthetic up keep. Overall, we enjoyed our star and felt very comfortable! Thank you Colin for being above and beyond host :)
Top Guest favourite
Condo in Lake View
4.99 out of 5 average rating, 179 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

StevenRating, 5 stars2 days ago
Will’s flat was exactly what my son and I needed on our trip to Chicago. It completely met our expectations and felt like home. My son was impressed with the comfort of the Murphy bed. The master bedroom was palatial and well-appointed. The kitchen had everything we needed, though we only used it for breakfast each day. As we were there primarily to take in a couple of baseball games we couldn’t have been happier with the location- Wrigley Field was only a few minutes away and we were close to the red line which took us to where the White Sox play. Will was very helpful with instructions and quick to respond to our questions. Absolutely would recommend this place without hesitation.
Guest favourite
Condo in West Town
4.92 out of 5 average rating, 121 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

MalloryRating, 5 stars4 days ago
Feven was very responsive to all our questions in real time. The place was perfect for four adults and two kids! The place was walkable to a few restaurants and coffee shops and easily drivable to other neighborhoods. We did happen to be in the neighborhood for the PR festival, which we didn’t realize. It made traffic a little tricky but otherwise we didn’t hear too much noise from the festivities. We found a nearby coffee shop and playground which we frequented daily and met lots of friendly neighbors on our walks.
Guest favourite
Condo in Lincoln Park
4.94 out of 5 average rating, 102 reviews

NEW luxury Old Town 1-Bedroom condo

JoniRating, 5 stars1 week ago
We loved staying here during our recent trip to Chicago. We were traveling with two young children, and the space was perfect for us. We were also grateful for the parking permits that allowed us to park nearby. The location was great—the neighbor was lovely, and we were happy to be so close to Lincoln Park. Overall, we’d recommend the space!
Guest favourite
Condo in Pilsen Historic District
4.94 out of 5 average rating, 126 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

MelissaRating, 5 stars1 week ago
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!
Superhost
Condo in Chicago
4.87 out of 5 average rating, 120 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

MelissaRating, 5 stars4 days ago
Awesome location, near lots of local restaurants, public transit and a major grocery store. China Town is a short bus ride away. The neighborhood itself is awesome, helpful neighbors and very friendly local vendors. The apartment itself is clean, inviting and has everything you could possibly need. Cory and Alexis were very inviting host, quick to respond to my questions and were very informative. I will be keeping this location in mind for my future Chicago travels.
Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 166 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

WilliamRating, 5 stars1 week ago
Crazy clean, super breezy place to stay. Neighborhood is fine, but not a lot of amenities. But it was a great place for us to be.
Top Guest favourite
Condo in Lake View
4.98 out of 5 average rating, 119 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

RebeccaRating, 5 stars2 weeks ago
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

Condo rentals with a pool

Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars1 month ago
I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.
Superhost
Condo in The Loop
4.73 out of 5 average rating, 55 reviews

2BD Central Downtown Location! Spacious & Cozy

MadleneRating, 5 stars1 month ago
We were very happy with the Apartment, it was clean and perfect size for 4 people. Ana was super helpful and responded immediately, we loved talking to her 😄 For me due to Images, and wrong adress on the public profile, there has been some confusion about the location of the Apartment. All in all: The views are not stunning, but the location is perfect for sightseeing (and price was great location wise)! 😉
Condo in The Loop
4.45 out of 5 average rating, 11 reviews

voco: Balcony & City View

AmitRating, 5 stars2 weeks ago
gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 108 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

StaciRating, 5 stars2 weeks ago
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.
Condo in Magnificent Mile
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Guest favourite
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favourite
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

FeiRating, 5 stars1 week ago
You can walk to Northwestern University, and the surrounding environment is clean, comfortable, and pleasant.The house is fully equipped, and I love cooking in the kitchen.Our whole family had a wonderful week here.Would stay again.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 101 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

AileenRating, 5 stars1 week ago
Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.

Quick stats about condo rentals in Oak Park

  • Total rentals

    10 properties

  • Nightly prices starting at

    $93 AUD before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 properties include access to Wi-Fi

Destinations to explore

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  3. Illinois
  4. Cook County
  5. Oak Park
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