Oakwood Hills Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Oakwood Hills Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
S$701
per person
21 Nov - 27 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
Great place to stay! The location is excellent, close to plenty of restaurants and just one mile from Millennium Park. Subway and bus stations are also nearby, making it easy to get around the city. The staff is very friendly and welcoming. I would definitely recommend this place!
Reviewed on 20 Oct, 2026
Top hotels in Oakwood Hills
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
Fully refundable
S$128
18 Nov - 19 Nov
includes taxes & fees
8/10 Very good! (1,510 reviews)
"Everything in this hotel excellent"
Reviewed on 20 Oct, 2026
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
Fully refundableReserve now, pay when you stay
S$83
4 Nov - 5 Nov
includes taxes & fees
7.2/10 Good! (1,462 reviews)
"It was in my price range and in a quiet area"
Reviewed on 20 Oct, 2026
Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
Fully refundable
S$142
15 Nov - 16 Nov
includes taxes & fees
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 holiday package cost?
You can pick up a holiday package to this destination from S$701 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?
- 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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
