Photo by Judy Mahoney

Oak Brook Holiday Rentals

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Holiday Rentals in Oak Brook

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (416)
"Great location for museum campus area!!!"
The price is NZ$407
includes taxes & fees
16 Jun - 17 Jun
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (88)
"Really pleased with my stay at the Market Hall. The process was extremely easy to reserve and access the room. The room was better than expected. I would definitely stay here again. Thanks Sonder!! "
The price is NZ$260
includes taxes & fees
16 Jun - 17 Jun
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"Everything was great!"
The price is NZ$370
includes taxes & fees
4 Jun - 5 Jun
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (243)
"Clean, friendly, spacious and at an excellent location."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (209)
"Nice"
The price is NZ$769
includes taxes & fees
4 Jun - 5 Jun
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$357
includes taxes & fees
27 Jun - 28 Jun
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (64)
" Cozy "
The price is NZ$452
includes taxes & fees
12 Jun - 13 Jun
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (33)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (103)
"Loved it "
The price is NZ$463
includes taxes & fees
18 Jun - 19 Jun
Sonder Jewelers Row
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is NZ$155
includes taxes & fees
4 Jun - 5 Jun
WoodSpring Suites Chicago Addison
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$408
includes taxes & fees
19 Jun - 20 Jun
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is NZ$370
includes taxes & fees
17 Jun - 18 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (200)
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is NZ$533
includes taxes & fees
25 Jun - 26 Jun
Sonder The Opal
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See all available properties in Oak Brook
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.

Other types of properties in Oak Brook you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6808)
"No hot water during whole stay. Had to shower in a fellow traveller's room."
The price is NZ$338
includes taxes & fees
5 Jun - 6 Jun
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2917)
"Pedro was so helpful from the point of arrival until check out! He was thorough in explaining any questions we had and they were very flexible with late check out as well. I will definitely return in the near future. "
The price is NZ$396
includes taxes & fees
17 Jun - 18 Jun
River Hotel
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very good, (1979)
"I loved the service we got. Would recommend staying here! "
The price is NZ$382
includes taxes & fees
16 Jun - 17 Jun
Eurostars Magnificent Mile
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oak Brook holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oak Brook. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oak Brook. Seeing all the best attractions is bound to make you fall in love with Oak Brook. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oak Brook short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Oak Brook?

Yes, there are holiday rentals close to the most popular sights in Oak Brook, 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 Brook. Leave time to check out the forests and entertainment venues during your visit.

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

Your Home Away From Home: This holiday home rental outside of Oak Brook offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

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

Cultural attractions include Lizzadro Museum of Lapidary Art and Graue Mill and Museum, whereas York Woods County Forest Preserve is one spot to enjoy nature. Other popular places to visit in the area include Wrigley Field and Grant Park.

What’s a holiday rental in Oak Brook like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Brook. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for families.

Recent reviews of Oak Brook properties
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