Oak Hill Vacation Packages
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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.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,126, price is now CA $837 per person
CA $837
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (420 reviews)
Great location off the highway. Short travel distance into downtown Chicago. Great stay!
Reviewed on Jun 19, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.
Reviewed on Jun 16, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,296, price is now CA $921 per person
CA $921
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
We stayed at this hotel for a small wedding venue. I booked the larger room and was glad I did. The hotel was close for walking to restaurants and some bars. The front desk was very friendly and helpful.
Reviewed on Jun 19, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,424, price is now CA $1,035 per person
CA $1,035
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun
Reviewed on Jun 17, 2026
Oak Hill Hotel Deals
The Ingleside Hotel
2810 Golf Road Pewaukee WI
The price is CA $151 per night from Jun 21 to Jun 22
CA $151
CA $171 total
Jun 21 - Jun 22
includes taxes & fees
8.6/10 Excellent! (834 reviews)
"The staff were incredibly helpful and friendly. Sarah at the front desk was particularly accommodating and cordial."
Reviewed on Jun 18, 2026
Fairview Inn & Suites Whitewater
917 E Milwaukee St Whitewater WI
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Jul 5 to Jul 6
CA $104
CA $118 total
Jul 5 - Jul 6
includes taxes & fees
5.4/10 (36 reviews)
"The room was clean and freshly painted. So freshly painted that the room still smelled strongly of paint. Breakfast was very disappointing. We were told it was " Grab and Go" .... Poptarts and nutrigrain bars. For families that have food allergies (like us) this was not good options."
Reviewed on Jun 16, 2026
Holiday Inn Express & Suites Delafield by IHG
3030 Golf Rd Delafield WI
Fully refundable
The price is CA $161 per night from Jul 19 to Jul 20
CA $161
CA $182 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (655 reviews)
"We saw the 9.4 rating and expectations were high. This hotel met our expectations. Slept well. Breakfast enjoyed."
Reviewed on Jun 18, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
