Oak Brook Vacation Rentals

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Dec 5 - Dec 6
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Oak Brook

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (998)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
$143 nightly
The price is $168
Dec 21 - Dec 22
Total with taxes and fees
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (393)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$223 nightly
The price is $262
Jan 5 - Jan 6, 2026
Total with taxes and fees
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (642)
"Clean facilities, great staff, good location "
United States
Emily
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (381)
"A very clean and spacious apartment with a great view. The parking garage right next to the building is very convenient. If the water pressure be improved, that will be perfect."
United States
Tammy
Kasa South Loop Chicago
Property entrance
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
$132 nightly
The price is $156
Dec 7 - Dec 8
Total with taxes and fees
Chicago luxury home suites
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
$86 nightly
The price is $102
Dec 7 - Dec 8
Total with taxes and fees
Wrigleyville Suites
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
$342 nightly
The price is $402
Dec 7 - Dec 8
Total with taxes and fees
Kasa River North Chicago
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
$172 nightly
The price is $197
Dec 7 - Dec 8
Total with taxes and fees
The Gem Museum Suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Apartment in Lakeview

9.0 out of 10, Wonderful, (38)
"Perfect for our needs, clean, convenient and great value. "
United States
Lisa B.
$150 nightly
The price is $165
Dec 8 - Dec 9
Total with taxes and fees
Clean & Equipped 1BR Apt
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

Condo in West Town

10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
$331 nightly
The price is $389
Dec 7 - Dec 8
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University

Apartment in Hyde Park

8.8 out of 10, Excellent, (15)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
$140 nightly
The price is $155
Dec 7 - Dec 8
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Apartment in Lakeview

9.2 out of 10, Wonderful, (27)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
$166 nightly
The price is $181
Dec 8 - Dec 9
Total with taxes and fees
Lakeview 2BR Apartment
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish 1BR in West Loop
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Apartment in Near West Side

10.0 out of 10, Exceptional, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
$167 nightly
The price is $182
Dec 7 - Dec 8
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Terrace/patio
Chicago Luxury Penthouse Gold Coast Best Location

Condo in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location
TV, offices
Modern West Loop Gem-City Views & Prime Location 6

Apartment in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great place"
United States
Daniel L.
Modern West Loop Gem-City Views & Prime Location 6
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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"great stay"
james 1-night trip
Posted 21 hours ago
Palmer House a Hilton Hotel

Find out more about Oak Brook

Everything you need to know about Oak Brook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Brook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Brook vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oak Brook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Brook rentals

At Expedia, we put the best Oak Brook vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Oak Brook?

Yes, you can find vacation rentals close to top points of interest in Oak Brook, or you can choose a more remote 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 vacation home rentals that Oak Brook has to offer?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: Visitors like this Oak Brook vacation home rental. It offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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 Lizzadro Museum of Lapidary Art and Graue Mill and Museum. Other popular places to visit in the area include Wrigley Field and Michigan Avenue.

What’s a vacation rental in Oak Brook like?

Vacation rentals are private properties you can stay in for a couple days or more in Oak Brook. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips or small group gatherings.