Oakwood Hills Holidays

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Top Flight + Hotel Deals in Oakwood Hills

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,420, price is now €868 per person
€868
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,794, price is now €1,081 per person
€1,081
per person
4 Oct - 10 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,443, price is now €873 per person
€873
per person
4 Oct - 10 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €2,271, price is now €1,396 per person
€1,396
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Top hotels in Oakwood Hills

Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is €67 per night from 11 Sept to 12 Sept
€67
11 Sept - 12 Sept
includes taxes & fees
6.6/10 (1,010 reviews)
"The room could have been cleaner, especially the bathtub/shower"

Reviewed on 23 Aug 2025

Wyndham Garden Schaumburg Chicago Northwest
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
The price is €106 per night from 2 Sept to 3 Sept
€106
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Great place to stay
"The staff was amazing, very helpful and friendly. The room was very comfortable, but needed some repair (Wallpaper peeling in multiple area's). The pool area is very spacious. The lobby is nice and accommodating with no rooms at that end so noise was not an issue."

Reviewed on 23 Aug 2025

DoubleTree by Hilton Libertyville - Mundelein
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
The price is €167 per night from 31 Aug to 1 Sept
€167
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,222 reviews)
"N"

Reviewed on 24 Aug 2025

Hyatt Regency Schaumburg Chicago
See all 667 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 holiday package cost?
You can pick up a holiday package to this destination from €868 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.