Oakwood Hills Packages (Flight + Hotel)

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Top Oakwood Hills Flight + Hotel Deals

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 20 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
There was an odd odor. My room was not ready for several hours after check in.

Reviewed on 17 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
I had a great stay. No complaints. The staff was great.

Reviewed on 17 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on 16 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 20 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The room is spacious and the bedding is comfortable. The washroom is sparkling clean. The breakfast buffet is an excellent addition to our stay. We all love it.

Reviewed on 18 Jul 2025

Frequently asked questions

How much does an Oakwood Hills holiday package cost?
You can pick up a holiday package to this destination from ฿13,736 on Expedia. But how much your holiday 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 holiday 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 holiday 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 holiday as a package?
An Expedia holiday package could land you great savings when compared to booking accommodation and flights separately. Better still, you can personalise 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 holiday 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 holiday 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.