An aerial view of a park with a lake, walking paths, tennis courts, and surrounding greenery.

Oak Brook Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Oak Brook holiday rentals

Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is HK$2,204
HK$5,042 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 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 HK$2,078
HK$4,713 total
includes taxes & fees
6 Jul - 7 Jul
River North Rooftop With In and Out Parking 3
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,819
HK$2,426 total
includes taxes & fees
7 Jul - 8 Jul
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is HK$3,717
HK$7,897 total
includes taxes & fees
2 Jul - 3 Jul
Modern West Loop Gem-City Views & Prime Location 4
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
Downtown Chicago Stay with Free In & Out Parking 5
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is HK$1,286
HK$1,713 total
includes taxes & fees
2 Jul - 3 Jul
LIVN West Loop Chicago Queen Superior Studio
2 bedrooms, desk, iron/ironing board, travel cot

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is HK$2,486
HK$5,274 total
includes taxes & fees
2 Jul - 3 Jul
South Loop Rooftop With In & Out Parking 1
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
The price is HK$1,260
HK$1,709 total
includes taxes & fees
5 Jul - 6 Jul
Sentral Michigan Avenue
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (24 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is HK$10,452
HK$16,710 total
includes taxes & fees
31 Jul - 1 Aug
Spacious 4BR Central Apartment w/ Skyline Views
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is HK$2,181
HK$2,753 total
includes taxes & fees
8 Jul - 9 Jul
Level Chicago – Old Town
TV, offices

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is HK$3,066
HK$5,627 total
includes taxes & fees
2 Jul - 3 Jul
River North Private Balcony With In and Out Parking
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is HK$1,659
HK$2,592 total
includes taxes & fees
5 Jul - 6 Jul
Kasa River North Chicago
Property grounds

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, (84 reviews)
"Great location for a short trip "
United States
Eric W.
The price is HK$1,123
HK$2,692 total
includes taxes & fees
5 Jul - 6 Jul
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Interior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
Modern 3BR Apartment Near North Ave Shops
Fridge, microwave, oven, stovetop

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 HK$1,853
HK$4,029 total
includes taxes & fees
7 Jul - 8 Jul
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Interior

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.
The price is HK$2,580
HK$6,310 total
includes taxes & fees
2 Jul - 3 Jul
Modern West Loop Gem-City Views & Prime Location 3
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is HK$3,096
HK$6,292 total
includes taxes & fees
8 Jul - 9 Jul
Vintage Urban Retreat
Dining

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (17 reviews)
"We would recommend this location and suite to anyone who has a need to visit in the greater Chicago area as apposed to staying in the city."
United States
David W.
The price is HK$2,007
HK$3,705 total
includes taxes & fees
28 Jul - 29 Jul
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Smart TV, books

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg
9.8 out of 10, Exceptional, (9 reviews)
"Super comfy for families and the nicest host. "
United States
Anonymous traveller
The price is HK$2,259
HK$4,640 total
includes taxes & fees
6 Jul - 7 Jul
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Highly recommend"
Clayton 2-night trip
Posted 2 hours ago
Hotel Riu Plaza Chicago

Find out more about Oak Brook

Search for holiday rentals in Oak Brook on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Brook using one of the methods below:

  • View our selection of featured holiday rentals in Oak Brook
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Look no further and take a look at our great range of rental properties in Oak Brook!

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Oak Brook is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease 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 Michigan Avenue.

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.