Oak Hill Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
Your Oak Hill Vacation
When you book a Oak Hill vacation package, it's all about letting go and enjoying your adventure to the fullest. Discover the best parts of this fun-filled city knowing that all your travel arrangements have been organized in advance. If sightseeing is on your list of things to do during your trip to Oak Hill, check out leading attractions like Palmyra Beach. Whoever you're taking a break with and whatever the size of your budget, your ultimate Oak Hill vacation is just a few clicks away with Expedia.
Top Oak Hill Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,487, price is now CA $1,004 per person
CA $1,004
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.
Reviewed on Apr 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,916, price is now CA $1,246 per person
CA $1,246
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .
Reviewed on Apr 17, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,293, price is now CA $1,570 per person
CA $1,570
per person
Jul 1 - Jul 5
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
The Langham is simply unparalleled! The staff, the amenities, the location, food and level of service are at such a high level, I find it unmatched anywhere else. Simply cannot wait to come back
I actually came to Chicago to see a concert, I had bought the tickets and the air travel and knew I was going to stay at the Langham but FORGOT to reserve the room! The staff worked with me for 1/2 an hour to shoehorn me into the almost capacity hotel for 2 nights! Amazong
Reviewed on Apr 18, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,526, price is now CA $1,069 per person
CA $1,069
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
Oak Hill Hotel Deals
The Ingleside Hotel
2810 Golf Road Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Apr 26 to Apr 27
CA $147
CA $166 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (789 reviews)
Someone Stole My Loafers Microwave Didnt Spin, Staff At Counter Dave Worked Sunday Evening Made Me Pay For An Extra Waterpark Pass Because I Booked Thru A 3rd Party So I Wouldn’t Recommend Booking That Way, Prices Were The Same. Room Wasn’t Clean Smelled Like Dog. O And Maintanence Woke Me And My ...
Reviewed on Apr 6, 2026
La Quinta Inn & Suites by Wyndham Milwaukee Delafield
2801 Hillside Dr Delafield WI
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Apr 26 to Apr 27
CA $121
CA $136 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Amazing
Reviewed on Apr 18, 2026
avid hotel Milwaukee West Waukesha by IHG
2101 Meadow Lane Pewaukee WI
Fully refundable
The price is CA $137 per night from Apr 26 to Apr 27
CA $137
CA $155 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (686 reviews)
Breakfast was good. Rooms were clean. A in room microwave would be nice.
Reviewed on Apr 19, 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.
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.
