Oak Hill Holidays
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Oak Hill
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €1,182, price is now €723 per person
€723
per person
13 Nov - 19 Nov
found 23 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on 25 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,320, price is now €1,397 per person
€1,397
per person
13 Nov - 19 Nov
found 23 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was €1,734, price is now €1,057 per person
€1,057
per person
13 Nov - 19 Nov
found 23 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,489, price is now €975 per person
€975
per person
13 Nov - 19 Nov
found 23 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on 26 Aug 2025
Level Chicago – Old Town
Downtown Chicago
Price was €1,287, price is now €852 per person
€852
per person
13 Nov - 19 Nov
found 23 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug 2025
Top hotels in Oak Hill
The Ingleside Hotel
2810 Golf Road, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is €104 per night from 31 Aug to 1 Sept
€104
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (694 reviews)
"Very nice stay, check-in was smooth and easy and check out a breeze. Nice big shower and comfortable room."
Reviewed on 25 Aug 2025
Best Western Waukesha Grand
2840 N Grandview Boulevard, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is €77 per night from 1 Sept to 2 Sept
€77
1 Sept - 2 Sept
includes taxes & fees
AmericInn by Wyndham Delafield-Waukesha-Milwaukee
2412 Milwaukee St, Delafield, WI
Fully refundableReserve now, pay when you stay
The price is €85 per night from 1 Sept to 2 Sept
€85
1 Sept - 2 Sept
includes taxes & fees
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.