Oak Park Holiday Rentals

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Holiday Rentals in Oak Park

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (35)
"Had a great stay! Thank you!"
Chic Suite/Mins to L Train /Laundry/Free Parking

Cozy modern unit w/ easy access to downtown Chi

9.4 out of 10, Exceptional, (34)
"Clean, exactly as described and reasonably priced. Also a great location to access public transit & lots of restaurants nearby. Had a great stay!"
Cozy modern unit w/ easy access to downtown Chi

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is AU$240
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is AU$101
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AU$220
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (332)
"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is AU$343
includes taxes & fees
25 Nov - 26 Nov
Level Chicago – Old Town

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is AU$209
includes taxes & fees
24 Dec - 25 Dec
Found Chicago powered by Sonder

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"The room is really cute and has all the amenities (including washing machine and dishwasher). Staying for business though I could hear quite a lot of noise from other rooms which made sleeping difficult at night "
The price is AU$251
includes taxes & fees
23 Dec - 24 Dec
Sonder The Burnham Apartments

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is AU$245
includes taxes & fees
23 Dec - 24 Dec
Sonder Jewelers Row

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is AU$153
includes taxes & fees
9 Dec - 10 Dec
Kasa River North Chicago

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is AU$202
includes taxes & fees
23 Dec - 24 Dec
Sonder The Plymouth

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is AU$229
includes taxes & fees
23 Dec - 24 Dec
Sonder The Opal

LakeHouse

10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

10.0 out of 10, Exceptional, (212)
"A big, beautiful, immaculate, wonderfully furnished space 51 floors above the city. Everything in the owner's description is true. Watching the sun rise over the lake from that height was a treat. Also being able to walk to restaurants, Navy Pier, river tours, great blues clubs, plus hop the subway just a few doors away. The door staff was very helpful in stashing our luggage on both sides of our stay (be sure to "show them some kindness" for that service). "
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (12)
"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "
Experience Chicago living near United Center
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Oak Park you may be interested in

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8199)
"Perfect Place To Stay! Walkable To Everything!"
The price is AU$233
includes taxes & fees
24 Nov - 25 Nov
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3569)
"Booked: two bedroom suite Condition: bed was very comfy and linens felt lovely. Bathroom was well appointed. Spotlessly clean. Rooms could use a remodel and a spruce up, BUT it was not offensively outdated and I have NO complaints on the quality of the space. Microwave also functions as a convection oven. Plates, cups, utensils, cooktop, pots and pans included. Refrigerator is fairly generously sized. Love the water bottle filler across from the elevator. Staff were fantastic, helpful and fun!...
The price is AU$180
includes taxes & fees
23 Dec - 24 Dec
River Hotel

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3297)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."
The price is AU$173
includes taxes & fees
23 Dec - 24 Dec
Club Quarters Hotel, Central Loop, Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Frequently asked questions

Are there holiday rentals in Oak Park?

Yes, there are holiday rentals in Oak Park close to Oak Park Conservatory, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Oak Park. While you're here, grab a bite or have a drink at the cafes.

What are some of the best holiday rentals that Oak Park has to offer?

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!: This holiday home rental outside of Oak Park is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Oak Park?

With 26 Expedia holiday rentals, you're guaranteed to find just the right place for your Oak Park stay.

What’s there to see and do in Oak Park?

Cultural attractions include Ernest Hemingway Museum and House and Madison Street Theatre, whereas Oak Park Conservatory and Mills Park are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Michigan Avenue.

What’s a holiday rental in Oak Park like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Park. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.