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Apartment holiday rentals in Oak Park

Find and book unique apartments on Airbnb

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Popular amenities for Oak Park apartment rentals

Weekly apartment rentals

Guest favourite
Apartment 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
Apartment 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
Apartment in Wrigleyville
4.98 out of 5 average rating, 373 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

JohnRating, 5 stars2 weeks ago
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.
Superhost
Apartment in Stickney
4.91 out of 5 average rating, 23 reviews

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

SilviuRating, 5 stars4 days 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
Apartment in Elmwood Park
4.6 out of 5 average rating, 15 reviews

Top Floor Condo near airport

ColleenRating, 5 stars4 weeks ago
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.
Superhost
Apartment in West Town
4.86 out of 5 average rating, 474 reviews

Humboldt Park Traveler's Lodge

NellRating, 5 stars3 weeks ago
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!
Guest favourite
Apartment in Skokie
4.91 out of 5 average rating, 108 reviews

Parking Terrace Near Universities Up to 20%OFF

JoevicRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Oak Park
4.88 out of 5 average rating, 64 reviews

Award winning historical building in Oak Park

HeatherRating, 5 stars1 week ago
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

Top guest favourite
Apartment in Lincoln Park
4.99 out of 5 average rating, 280 reviews

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

MeganRating, 5 stars3 days ago
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!
Superhost
Apartment in Pilsen Historic District
4.84 out of 5 average rating, 134 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

HasimeRating, 5 stars1 month ago
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.
Top guest favourite
Apartment in Lake View
4.99 out of 5 average rating, 178 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RonniRating, 5 stars2 days ago
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.
Guest favourite
Apartment in Bridgeport
4.9 out of 5 average rating, 117 reviews

Convenient & Spacious 3BR Condo w/Free Parking

CatherineRating, 5 stars1 week ago
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
Guest favourite
Apartment in West Town
4.92 out of 5 average rating, 121 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

MalloryRating, 5 stars1 day 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
Apartment in Pilsen Historic District
4.94 out of 5 average rating, 126 reviews

Stunning 4BR/2.5 BA w/ 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
Apartment in Chicago
4.87 out of 5 average rating, 119 reviews

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

AnneRating, 5 stars3 weeks ago
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.
Top guest favourite
Apartment in Edgewater
4.97 out of 5 average rating, 118 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

SincereeRating, 5 stars1 week ago
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

Guest favourite
Apartment 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.
Guest favourite
Apartment 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.
Apartment 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.
Apartment 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.
Apartment in Lombard
4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago
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.
Guest favourite
Apartment 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
Apartment in Evanston
4.91 out of 5 average rating, 126 reviews

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

FeiRating, 5 stars4 days ago
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。
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 100 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 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

Destinations to explore

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  5. Oak Park
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