Oak Brook Holiday Rentals

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Our top choices for Oak Brook holiday rentals

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is NZ$1,090
includes taxes & fees
21 May - 22 May
River North Rooftop With In and Out Parking 3

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is NZ$544
includes taxes & fees
10 May - 11 May
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is NZ$523
includes taxes & fees
20 May - 21 May
Modern Comfort: 1BR Unit w/ Laundry

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
Modern West Loop Gem-City Views & Prime Location 5

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is NZ$435
includes taxes & fees
20 May - 21 May
Chic Studio in the Heart of the Gold Coast

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
River North Private Deck With In and Out Parking

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is NZ$549
includes taxes & fees
14 May - 15 May
West Loop Living – Bright 1BR

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (751 reviews)
"Excellent stay, clean and efficient. So much better than a hotel"
United States
Robin
The price is NZ$403
includes taxes & fees
10 May - 11 May
Kasa Magnificent Mile Chicago

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is NZ$368
includes taxes & fees
13 May - 14 May
LIVN Millennium Park Downtown Chicago 2BR

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is NZ$1,826
includes taxes & fees
17 May - 18 May
Downtown Chicago Stay with Free In & Out Parking 4

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is NZ$295
includes taxes & fees
10 May - 11 May
LIVN West Loop Chicago King Studio

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (474 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is NZ$495
includes taxes & fees
11 May - 12 May
Level Chicago – Old Town

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is NZ$788
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,153 reviews)
"Thank you for the stay"
United States
Marco
The price is NZ$349
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
Modern West Loop Gem-City Views & Prime Location 6

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.8 out of 10, Good, (7 reviews)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is NZ$330
includes taxes & fees
11 May - 12 May
Uptown Studio Gem Sum

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is NZ$727
includes taxes & fees
11 May - 12 May
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is NZ$618
includes taxes & fees
25 May - 26 May
Kasa River North Chicago

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.2 out of 10, Wonderful, (18 reviews)
"Really great location. Clark street is great but can be a little noisy at night. "
United States
Adam
The price is NZ$554
includes taxes & fees
11 May - 12 May
Stylish and Roomy 2BR in Chicago

Cozy Train Vibes + Rare Parking x3

Cozy Train Vibes + Rare Parking x3
North Center
10.0 out of 10, Exceptional, (18 reviews)
"It was a great spot to be, we loved it! The hosts were super responsive and helped resolve all our questions. Would absolutely stay there again if needed :) "
United States
Jenna P.
Cozy Train Vibes + Rare Parking x3
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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Top Oak Brook Hotel Reviews

Find out more about Oak Brook

Everything you need to know about Oak Brook holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Brook holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Brook holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oak Brook holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Brook. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Brook holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Brook holiday rentals we have selected for you start as low as NZ$250 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oak Brook rentals

At Expedia, we put the best Oak Brook holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Brook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Brook holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Brook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Oak Brook is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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

Enjoy the outdoors at Mayslake Forest Preserve Dog Park and York Woods County Forest Preserve, or simply take in cultural attractions like Graue Mill and Museum and Lizzadro Museum of Lapidary Art. Other popular places to visit in the area include Wrigley Field and United Center.

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.