Oakwood Hills Vacations from ￥308,218

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The Latest Oakwood Hills Vacation Packages

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The hotel is beautiful inside and out and the staff are super nice and helpful. Hotel is in a very crowded area. It can take time to get in and out with your car. A lot of noise from the outside even when staying on top floors. Hotel could be managed better. Elevator was broken for a whole day. Room had some minor repairs that were not done when we checked in.

Reviewed on Jul 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul 21, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 10 - Oct 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul 26, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Very nice location super friendly staff very modern and clear hotel

Reviewed on Jul 27, 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,042 reviews)
Beautiful Hotel! Rooftop pool is wonderful!

Reviewed on Jul 27, 2025

Find the Best Oakwood Hills Vacation Packages

Oakwood Hills Hotel Deals

DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
75 W Algonquin Rd, Arlington Heights, IL
Fully refundableReserve now, pay when you stay
The price is ￥13,683 per night from Aug 10 to Aug 11
￥13,683
￥15,322 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"Very Good Service"

Reviewed on Jul 22, 2025

DoubleTree by Hilton Chicago - Arlington Heights
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ￥13,056 per night from Aug 4 to Aug 5
￥13,056
￥15,011 total
Aug 4 - Aug 5
includes taxes & fees
7/10 Good! (875 reviews)
Surprisingly Good
"It was very nice. A comfortable getaway from my norm."

Reviewed on Jul 23, 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,575 per night from Aug 3 to Aug 4
￥17,575
￥20,208 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,180 reviews)
"It was a lovely hotel and close to wonderful restaurants and the mall."

Reviewed on Jul 27, 2025

Hyatt Regency Schaumburg Chicago
See all 672 properties in Oakwood Hills
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 ￥308,218 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.