Oakwood Hills Vacations from ￥425,110
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
The Latest Oakwood Hills Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥433,374
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Family friendly, beautiful views. Easy public transportation available.
Reviewed on Aug 7, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
￥467,066
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,432 reviews)
I thought the property was nice enough . We were on the fourth floor across from the ice maker , which we could hear marking ice . Not the best when you’re laying $600 a night .
Reviewed on Aug 6, 2026
Find the Best Oakwood Hills Vacation Packages
Oakwood Hills Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
￥23,612
￥26,913 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"It was a great experience!"
Reviewed on Aug 6, 2026
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
Fully refundableReserve now, pay when you stay
￥14,101
￥16,214 total
Sep 6 - Sep 7
includes taxes & fees
6.8/10 (1,012 reviews)
"Limpio y a buen precio"
Reviewed on Aug 6, 2026
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd Arlington Heights IL
Fully refundableReserve now, pay when you stay
￥16,763
￥18,772 total
Aug 23 - Aug 24
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Thank you for a fun and great time. The breakfast was amazing!"
Reviewed on Aug 7, 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.
Frequently asked questions
How much does an Oakwood Hills vacation package cost?
You can pick up a vacation package to this destination from ￥425,110 on Expedia. But how much your vacation to Oakwood Hills costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Oakwood Hills?
January, February and March are the best times to search for cheap Oakwood Hills vacation packages. Opting to travel in less busy periods means you can generally find reduced prices on hotels and flights.
How many days is enough for Oakwood Hills?
The ideal duration for your Oakwood Hills vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to go to all the main attractions and discover some hidden spots along the way.
How to find the best Oakwood Hills package deals?
Bagging a cheap Oakwood Hills package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Oakwood Hills package deals. Want a simple trick to score 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 Oakwood Hills vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can personalize your Oakwood Hills getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oakwood Hills?
If you're planning a spur-of-the-moment Oakwood Hills adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Oakwood Hills?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Oakwood Hills.
- Set a budget: Consider expenses such as food, flights and transportation when calculating how much to put aside for your trip to Oakwood Hills. Then, choose a property that suits your budget, whether that's a low-cost option or a more upscale getaway.
- Decide your trip length: Consider how long you'd like to spend exploring Oakwood Hills. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find an Oakwood Hills vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
