Oak Hill Vacations from $287

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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.

The Latest Oak Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $287 per person
$287
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was good and staff was very nice

Reviewed on Dec 9, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $613, price is now $375 per person
$375
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $485, price is now $297 per person
$297
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $640, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.

Reviewed on Nov 30, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $480, price is now $311 per person
$311
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,947 reviews)
Everything was wonderful. Property was beautiful. Arrived early and room was ready for check in at 1pm. Wonderful!! Staff was friendly. Old Fashioned in Amuse was superb!

Reviewed on Dec 8, 2025

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Oak Hill Hotel Deals

The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Dec 11 to Dec 12
$134 total
Dec 11 - Dec 12
Total with taxes and fees
8.4/10 Very Good! (756 reviews)
I have stayed at this location several times and intend to return. However a bit disappointed that the room I initially selected was changed at the last minute. Another disappointment was the fact that there was no microwave available in the room.

Reviewed on Dec 4, 2025

The Ingleside Hotel
Days Inn by Wyndham Johnson Creek

Days Inn by Wyndham Johnson Creek

2 out of 5
W 4545 Linmar Lane Johnson Creek WI
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $65 total per night from Dec 14 to Dec 15
$65 total
Dec 14 - Dec 15
Total with taxes and fees
7.6/10 Good! (848 reviews)
Yes

Reviewed on Nov 20, 2025

Days Inn by Wyndham Johnson Creek
Best Western Waukesha Grand

Best Western Waukesha Grand

2.5 out of 5
2840 N Grandview Boulevard Pewaukee WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $77 total per night from Dec 28 to Dec 29
$77 total
Dec 28 - Dec 29
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
Room was clean, had what we needed

Reviewed on Dec 6, 2025

Best Western Waukesha Grand
See all 246 properties in Oak Hill
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.

Find the Best Oak Hill Vacation Packages

Oak Hill Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does an Oak Hill vacation package cost?
You can snap up a vacation package to this popular destination from $287 on Expedia. However, how much your vacation to Oak Hill costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Oak Hill?
September, November and December are the best times to look for cheap Oak Hill vacation packages. Traveling in less busy periods means you can usually find lower prices on flights and hotels.
How many days is enough for Oak Hill?
Typically, a handful of days is enough to tick off the main attractions during your Oak Hill vacation. But if you want to have more time to unwind or take day tours, think about extending your trip.
How to find the best Oak Hill package deals?
Landing a cheap Oak Hill package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most affordable Oak Hill package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Oak Hill vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your Oak Hill trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Oak Hill?
If you're planning a spur-of-the-moment Oak Hill adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Oak Hill vacation packages?
Your Oak Hill getaway should be an escape from your daily routine, not a source of money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.