
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.

Sunny Apartment Just 2 Blocks from Wrigley and Boystown
My sister and I had a great time in Chicago. The location and accommodations were perfect! A block and 1/2 from Wrigley, yes we saw a game and the Cubs win! A block and 1/2 away from the “L” and a quiet neighborhood. The inside had everything we needed to make breakfast, sleep and relax on the backside porch sipping champagne. Would give this place 6 stars if I could. Thanks Mike for being a great host.

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

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.

Humboldt Park Traveler's Lodge
We would love to stay here again! It's a great neighborhood, really walkable, lots of cool buildings to look at and friendly neighbors. We walked across Humboldt Park to the 606 and had a great urban hike. No problem with transportation or food delivery, but we also enjoyed walking to markets and restaurants nearby. The space was so cozy and comfortable... well equipped kitchen, great couch for watching TV and movies, comfortable bed and bathroom. We really appreciated the host's great recommendations, all of them were spot on!

Parking Terrace Near Universities Up to 20%OFF
Such an awesome place to stay, very safe neighborhood. Mark was very responsive in the chat and asked us if we needed anything else right after we checked in. The best part was that their is a dedicated parking space which is very convenient and easy access to the place. For sure will be checking in next time when going to Chicago.

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

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
We loved our stay at Danny's place! This was our first time visiting Lincoln Park, and the location of the home was perfect. We walked to restaurants, the Lincoln Park Zoo, and the beach. We appreciated being able to have our dogs with us and found the area very dog-friendly on our walks. Danny was kind and thoughtful with all the extra touches and responsive communication. He even caught us in person to make sure we had everything we needed. Our family felt safe walking in the neighborhood day and night. We even took the bus to downtown Chicago, which is only a few miles away. The house itself was very clean and large - our family of 4 plus 2 dogs had plenty of room to spread out and feel comfortable. We highly recommend the home to others and hope we can return again someday!

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.

Convenient & Spacious 3BR Condo w/Free Parking
Good location. Condo was very clean with comfy beds. There are 3 flights of stairs to get to condo- no problem for us but be aware

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
Excellent séjour en famille chez Cory. Il a été toujours très réactif à nos interrogations. Logement spacieux , confortable. Il été agréable de s’y reposer le soir après de longues marches dans Chicago. Nous recommandons vivement.

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.
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
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

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
可以步行到西北大学,周边环境整洁舒适宜人。屋内设施齐全,很喜欢在厨房cooking。我们全家在这里度过了愉快的一周。下次还会入住。

"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