
Apartment holiday rentals in Oak Park
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Top-rated apartment rentals in Oak Park
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Weekly apartment rentals

Urban Oasis Getaway. 6 stops to downtown!
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!

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

1st Floor Condo Apartment Close to Midway Airport
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!

University of Chicago Condo-Upgraded and Spacious
13/10 stars ✨. Run do not WALK on this property for booking. I don’t even know where to start! i’ll try to keep it short! This property and Host has been the best i’ve ever experienced, Everrr!. Let’s start at the bathroom the tub is huge and deep- the perfect relaxation at your finger tips.. Spacious Home and beautifully decorated.. and Clean.. When you enter the home the fresh clean smells takes you over.. from the personalized birthday note to snacks to checking in to making sure everything was to my liking .. Chef’s kiss ❣️ Diane’s place is a piece of Heaven snuggled in the city of Chi-Town! Ladiessss if you need the perfect home to feel like a princess on every level book nowww.. This property has the best combo for a man or woman ! i can go on and on but just make sure when y’all book - you leave some dates open because i’m coming back here EVERY time❣️😘

Quick Drive to Downtown Chicago & Early Check-In
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.

Top Floor Condo near airport
There were four of staying at Issa’s home, and it was incredibly comfortable and clean. It was really nice to have access to a full kitchen, and both bathrooms were great. Would definitely recommend to anyone needing a comfortable stay with lots of room.

Wicker Park/Bucktown condo with large balcony
We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!

Award winning historical building in Oak Park
Our stay was very comfortable and the place is quite spacious. Dan let us check out a couple hours late as well which was convenient for us. I would stay here again if we visit Oak Park. It was right near the Main Street so we had access to a lot of cafes and restaurants.
Pet-friendly apartment rentals

816 PLZN Luxury Apt | Rooftop | Garage Parking
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
Beautiful, clean unit and Will was extremely responsive and helpful. Super clean, and the beds and furniture were soooooo comfortable! It looks exactly as it does in the photos and there are so many items included, in case you forgot something! A foot massager?! Amazing 🤣The location is perfect with lots to do close by and no shortage of options for places to eat. I feel extremely fortunate that I came across this one and will definitely book again in the future. Just perfect.

Luxuriously bright 3-bedroom condo: The Treehouse
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.

Stunning 4BR/2.5 BA w/ Outdoor Lounge | Sleeps 10+
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!

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT
Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.

Susie's Space. 2BR easy parking & pet friendly
Great neighbourhood! Susan was very communicative and a great host. Highly recommend.

Steps from the Lake, Lovely 3-Bedroom Condo
This home was the perfect space for my family while in Chicago. The rooms are bright and eclectic in decor. We felt at home within and will love to stay again on our next visit to Chicago.

Modern Luxury In Old Town - Sleeps 4
We had a great stay. We love this area of Chicago so we were so pleased with the location. Robert is very responsive and was a great host!
Apartment rentals with a pool

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

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Our Stay at The Bliss of Evanston was great. The host is very responsive and was very accommodating of our requests. The location and view can not be beat.

voco: Balcony & City View
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.

30 E. Huron #2603 Private Residence
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.

Just remodeled apartment close to airport and mall
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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

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

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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 apartment rentals in Oak Park
Total rentals
10 properties
Nightly prices starting at
₹5,180 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
Wifi availability
10 properties include access to wifi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club