Oak Brook Holidays from NZ$2,826
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Oak Brook Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Westin Chicago Lombard
Price was NZ$3,315, price is now NZ$2,826 per person
NZ$2,826
per person
13 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,267 reviews)
Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has gone down hill for sure
Reviewed on 25 May 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was NZ$4,055, price is now NZ$3,237 per person
NZ$3,237
per person
12 Aug - 17 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (2,312 reviews)
It was a clean room but in AM ready to go in bathroom and who comes out of the bathroom was a large brown cockroach!
Yikes!
Reviewed on 29 May 2026
Hilton Rosemont Chicago O'Hare
Price was NZ$4,302, price is now NZ$3,509 per person
NZ$3,509
per person
12 Aug - 17 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (1,004 reviews)
The room was clean and the staff were very nice and helpful. My only complaint is that the hotel is clearly dated and worn. They are undergoing a renovation, but our room was one of the older ones. The room was still fine, but the sink water pressure was very low. They did offer to have an engineer look at, but since our stay was so short we didn't bother with it.
Reviewed on 18 May 2026
Embassy Suites by Hilton Chicago O'Hare Rosemont
Price was NZ$3,674, price is now NZ$3,097 per person
NZ$3,097
per person
12 Aug - 17 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,374 reviews)
Very nice interior in this hotel and I loved my 1 bedroom big unit.
There is nice breakfast available and social hour, however bartender was rude.
Bathtub was not perfectly clean.
No shower handle, only shower head.
Overall hotel a little dates but the beds were very comfortable
Reviewed on 30 May 2026
Oak Brook Holiday
Our pick of the best Oak Brook Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$258 per night from 29 June to 30 June
NZ$258
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,125 reviews)
"Great location and clean"
Reviewed on 29 May 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$423 per night from 30 June to 1 July
NZ$423
30 June - 1 July
includes taxes & fees
9.4/10 Exceptional! (4,292 reviews)
"We did find some small issues with the cleanliness of the room. Great location. Beautiful hotel. Amazing rooftop bar experience. We had a great stay."
Reviewed on 30 May 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is NZ$302 per night from 29 June to 30 June
NZ$302
29 June - 30 June
includes taxes & fees
7.8/10 Good! (1,489 reviews)
"Great"
Reviewed on 30 May 2026
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.
Discover the most popular places to visit in Oak Brook
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
What to do in Oak Brook
Skydeck - Willis Tower Admission
NZ$74
per adult
96% of travellers recommend
Chicago Sightseeing River and Lake Cruise
NZ$77
per adult
100% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
