Oak Brook Vacation Rentals

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Check prices for these dates

Tonight
Dec 14 - Dec 15
Tomorrow
Dec 15 - Dec 16
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Oak Brook vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ￥18,409
￥26,182 total
includes taxes & fees
Dec 21 - Dec 22
Sentral Michigan Avenue
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
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
The price is ￥16,406
￥19,258 total
includes taxes & fees
Dec 16 - Dec 17
Chicago luxury home suites
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Business center
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
TV, offices
Modern West Loop Gem-City Views & Prime Location 4

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.
The price is ￥20,723
￥56,827 total
includes taxes & fees
Dec 22 - Dec 23
Modern West Loop Gem-City Views & Prime Location 4
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

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)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥12,309
￥32,086 total
includes taxes & fees
Dec 16 - Dec 17
Twice as Nice: Chic 2BR Stay with Style & Space
Interior
Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
2.0 star property
Downtown Chicago
The price is ￥18,697
￥53,943 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Downtown Chicago Stay with Free In & Out Parking 3
Interior
Your Chicago get Away

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.
The price is ￥27,485
￥59,512 total
includes taxes & fees
Dec 17 - Dec 18
Your Chicago get Away
Interior
Gold Coast Living: Modern Studio Unit

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
The price is ￥10,751
￥25,788 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 4 - Jan 5, 2026
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

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
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

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.
The price is ￥20,567
￥55,673 total
includes taxes & fees
Dec 27 - Dec 28
River North Rooftop With In and Out Parking 1
Fridge, microwave, oven, stovetop
South Loop Rooftop With In and Out Parking 3

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.
The price is ￥27,111
￥65,286 total
includes taxes & fees
Dec 19 - Dec 20
South Loop Rooftop With In and Out Parking 3
Outdoor dining
Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (8)
"Great stay. Very clean. Comfortable beds. Great location "
United States
shannon u.
The price is ￥98,004
￥175,158 total
includes taxes & fees
Dec 18 - Dec 19
Spacious 4BR Central Apartment w/ Skyline Views
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

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.
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

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.
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sun-Drenched 1BR Apartment
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is ￥137,346
￥193,971 total
includes taxes & fees
Dec 18 - Dec 19
ENVITAE Hotel 4 Bedroom Luxury Apartments
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The One: A 1BR Stay That Feels Like Home
Terrace/patio
River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is ￥58,740
￥108,738 total
includes taxes & fees
Dec 26 - Dec 27
River North Private Deck With In and Out Parking
Outdoor dining
Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1)
"Nice place, clean property, great views "
United States
Zach L.
The price is ￥98,004
￥175,158 total
includes taxes & fees
Dec 18 - Dec 19
Premium Urban 4BR - Perfect Mix of Comfort & Location
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Breakfast was delicious as always. But being in Chicago at this time of year, no AC was needed. LoL. Staff was exceptional! No complaints other than our room was directly in front of the elevator so it was a little loud on occasion 😔 but at the same time, it was convenient. ☺️"
Beverly 3-night trip
Posted 4 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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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  • Enter your travel dates to view the best deals on holiday rentals in Oak Brook while they last

Look no further and take a look at our great range of rental properties in Oak Brook!

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?

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: Visitors like this Oak Brook vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of games.

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.