Oak Hill Vacations from ￥246,450

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Oak Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
This was an amazing hotel, polite staff and accommodating as well.

Reviewed on Jul 12, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Gorgeous room with a breathtaking view!

Reviewed on Jul 10, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun 13, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul 8, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul 12, 2025

Find the Best Oak Hill Vacation Packages

Oak Hill Hotel Deals

La Quinta Inn & Suites by Wyndham Milwaukee Delafield
La Quinta Inn & Suites by Wyndham Milwaukee Delafield
3 out of 5
2801 Hillside Dr, Delafield, WI
Fully refundableReserve now, pay when you stay
The price is ￥14,065 per night from Jul 20 to Jul 21
￥14,065
￥15,893 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Need more TV Channels....
"Hotel and room were very clean....nice big tv but very very limited channels....nice area surrounding"

Reviewed on Jul 8, 2025

La Quinta Inn & Suites by Wyndham Milwaukee Delafield
The Ingleside Hotel
The Ingleside Hotel
4 out of 5
2810 Golf Road, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is ￥15,661 per night from Jul 21 to Jul 22
￥15,661
￥17,698 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (648 reviews)
Stay in Waukesha
"Staff was excellent. Bed was too soft and pillows were too lumpy."

Reviewed on Jul 9, 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
The price is ￥9,082 per night from Aug 3 to Aug 4
￥9,082
￥9,582 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (788 reviews)
"Great location near many amenities"

Reviewed on Jul 7, 2025

Days Inn by Wyndham Johnson Creek
See all 233 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.

Frequently asked questions

How much does an Oak Hill vacation package cost?
You can snap up a vacation package to this popular destination from ￥246,450 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?
If you're hoping to snag a cheap Oak Hill vacation package, consider visiting in January, February and November. You'll generally find lower prices on hotels and airfares during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Oak Hill?
With a well-organized schedule, you can easily visit the most popular Oak Hill attractions in a handful of days. But if you want to explore off the beaten track or go on day trips, think about booking your Oak Hill vacation for longer.
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.
How to plan a trip to Oak Hill?

  1. Pick your dates: What you want to do in Oak Hill and your favorite season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Oak Hill.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Oak Hill. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Oak Hill vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.