Oakbrook Terrace Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Oakbrook Terrace holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1019)
"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 S$216
includes taxes & fees
24 Dec - 25 Dec
Sentral Michigan Avenue
Exterior
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (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
The price is S$199
includes taxes & fees
4 Jan - 5 Jan, 2026
Chicago luxury home suites
Lounge
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
Full-sized fridge, microwave, oven, stovetop
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (403)
"Great location, clean room and friendly staff!"
United States
Scott
The price is S$250
includes taxes & fees
28 Dec - 29 Dec
Level Chicago – Old Town
Interior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is S$280
includes taxes & fees
21 Jan - 22 Jan, 2026
Chicago Third Floor Studio by 747 Lofts
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 Oakbrook Terrace Hotel Reviews

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
"The staff were wonderful! The only thing I missed in the room was a desk."
Lillian 4-night trip
Posted 6 hours ago
Silversmith Hotel Chicago Downtown

Frequently asked questions

Can I find holiday rentals in Oakbrook Terrace?

Yes, there are holiday rentals close to the most popular sights in Oakbrook Terrace, 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 Oakbrook Terrace. Leave some time to check out the zoo and entertainment venues during your trip.

What’s there to see and do in Oakbrook Terrace?

While exploring the area, visit family-friendly sights like Addison Ice Arena, or get outside and enjoy nature at Morton Arboretum. Oakbrook Center Mall and Drury Lane Theater are other places to visit while you're in town.

What’s a holiday rental in Oakbrook Terrace like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakbrook Terrace. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for families.