Oak Brook Vacation Rentals

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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Vacation Rentals in Oak Brook

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
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
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"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 8 - Dec 9
Total with taxes and fees
Chicago luxury home suites
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (394)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$223 nightly
The price is $262
Jan 4 - Jan 5, 2026
Total with taxes and fees
Level Chicago – Old Town
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5

2.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$276 nightly
The price is $299
Dec 17 - Dec 18
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

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.
$187 nightly
The price is $206
Dec 11 - Dec 12
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
West Loop Living – Bright 1BR
Interior
Your Chicago get Away

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
$386 nightly
The price is $422
Dec 11 - Dec 12
Total with taxes and fees
Your Chicago get Away
Living area
Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6

2.0 star property
Downtown Chicago
$440 nightly
The price is $490
Dec 26 - Dec 27
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 6
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"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.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sun-Drenched 1BR Apartment
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (4)
"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
$149 nightly
The price is $166
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 9 - Dec 10
Total with taxes and fees
Kasa River North Chicago
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

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
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
$375 nightly
The price is $414
Dec 19 - Dec 20
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$325 nightly
The price is $356
Dec 14 - Dec 15
Total with taxes and fees
River North Rooftop With In and Out Parking 1
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Location was extremely ideal. Staff very responsive. All the apartments were very clean. The pictures were very accurate to what you can expect"
Canada
john Z.
River North Rooftop With In and Out Parking 6
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
$345 nightly
The price is $379
Dec 18 - Dec 19
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
TV, offices
Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
$327 nightly
The price is $358
Dec 22 - Dec 23
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
Fridge, microwave, dishwasher, coffee/tea maker
Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
$410 nightly
The price is $455
Dec 30 - Dec 31
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Thank to Mr.Robert for getting a good room with a beautiful view of the river "
Armando 4-night trip
Posted 16 hours ago
The Royal Sonesta Chicago Downtown

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 $103 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.