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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 £444
includes taxes & fees
25 May - 26 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 £161
includes taxes & fees
26 May - 27 May
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (28 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
United States
shayna j.
The price is £1,471
includes taxes & fees
18 Jun - 19 Jun
3BR Luxury Suite w/Gym and Balcony

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 £169
includes taxes & fees
26 May - 27 May
LIVN Millennium Park Downtown Chicago 2BR

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 £507
includes taxes & fees
24 May - 25 May
Spacious 4BR Central Apartment w/ Skyline Views

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, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is £161
includes taxes & fees
1 Jun - 2 Jun
Chic Studio in the Heart of the Gold Coast

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 £161
includes taxes & fees
26 May - 27 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, (762 reviews)
"Great place to stay."
United States
Benedictine
The price is £168
includes taxes & fees
25 May - 26 May
Kasa Magnificent Mile Chicago

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is £166
includes taxes & fees
25 May - 26 May
LIVN West Loop Chicago 2 BR City View

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Perfect Stay!"
United States
Miyauna G.
Downtown Chicago Stay with Free In & Out Parking 3

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is £161
includes taxes & fees
26 May - 27 May
Chicago-Themed 1BR in a Central Spot near Downtown

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,172 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is £155
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (480 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is £173
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is £187
includes taxes & fees
26 May - 27 May
1BR Modern Luxe Apt with In-Unit Laundry

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.
The price is £334
includes taxes & fees
26 May - 27 May
Cozy Train Vibes + Rare Parking x3

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.
The price is £681
includes taxes & fees
3 Jun - 4 Jun
Modern West Loop Gem-City Views & Prime Location 5

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (74 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is £252
includes taxes & fees
25 May - 26 May
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

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, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is £562
includes taxes & fees
17 Jun - 18 Jun
Modern West Loop Gem-City Views & Prime Location 6

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
South Evanston
10.0 out of 10, Exceptional, (37 reviews)
"Excellent property and host. Truly enjoyed our stay. "
United States
Shashi Y.
The price is £215
includes taxes & fees
25 May - 26 May
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
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, apart-hotels, 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 £128 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.