Oak Brook Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Oak Brook Holiday
Our pick of the best Oak Brook Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$213
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,203 reviews)
"The hotel is old and needs a renovation. Carpets are worn and dirty, and you can tell that it hasn't had a refresh in 30+ years. However, we left important medicine behind and we coordinated with them to have it sent to us at our next stop...they were VERY helpful in this regard so despite a negative ..."
Reviewed on 29 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$287
31 Aug - 1 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
NZ$458
18 Sept - 19 Sept
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.
Stay near popular Oak Brook attractions
Oak Brook Golf Course
8.2/10 (147 reviews)
This championship course designed by Roger Packard and Dennis Wise challenges golfers with varied layouts and water hazards. Arrive early to practice on the expansive driving range before tackling its manicured fairways.
Photo by Judy Mahoney
Graue Mill and Museum
8.4/10 (94 reviews)
This historic waterwheel gristmill served as an Underground Railway station while grinding grain in the 1800s. Visitors can watch live milling demonstrations and explore interactive exhibits on 19th-century crafts.
Oakbrook Center Mall
9.2/10 (585 reviews)
Stroll through this upscale open-air shopping destination with over 160 speciality stores from Gucci to Apple. Beautifully landscaped walkways connect luxury retailers, dining options, and entertainment venues.
Mayslake Peabody Mansion
8.2/10 (92 reviews)
This Tudor Revival mansion offers a glimpse into the opulent lifestyle of coal magnate Francis Peabody. Tour the intricate woodwork and period architecture, then explore the serene 87-acre forest preserve surrounding it.
Lizzadro Museum of Lapidary Art
8.2/10 (74 reviews)
Marvel at intricate gemstone carvings and Chinese jade sculptures at this unique lapidary art museum. Explore the stunning blue jade imperial pagoda and learn about the ancient art of stone cutting.
Rush Oak Brook
If Rush Oak Brook is what brings you to town, hopefully you'll have a chance to explore more of Oak Brook.
What to do in Oak Brook
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
90% of travellers recommend
Frequently asked questions
How much does an Oak Brook holiday package cost?
You'll find cheap prices on Expedia for your Oak Brook escape. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Oak Brook costs.
What are the cheapest months to go to Oak Brook?
You can typically find reduced prices and better availability in January, February and April. Take a look at our cheap Oak Brook holiday packages and you could get some great off-season discounts.
How many days is enough for Oak Brook?
Oak Brook holidays come in many shapes and sizes, but to get a true feel for this destination, we reckon 2 days is about right. In this timeframe, you can visit major attractions like Oak Brook Golf Course and Oakbrook Centre Mall and seek out some lesser-known spots. Don't skip neighbourhoods such as Yorkfield and York Centre either. If you're clever with your time, you may even be able to take a day trip outside of Oak Brook too.
Is it worth booking a holiday package to Oak Brook?
Boasting a host of highlights starting with its amazing golfing, Oak Brook is a good holiday destination. Whether you'd like to discover sights like Mayslake Peabody Mansion and Lizzadro Museum of Lapidary Art or take the road less traveled, you'll have loads to keep you busy during your Oak Brook holiday.
How to find the best Oak Brook package deals?
Start your search for an Oak Brook package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Oak Brook package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oak Brook escape underway.
Is it cheaper to book an Oak Brook holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and accommodation individually. Better still, you can personalise your Oak Brook trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Oak Brook?
If you're planning an impromptu Oak Brook getaway, 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 score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Oak Brook?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Oak Brook.
- Set a budget: Factor in expenses like food, flights and transportation when calculating how much to set aside for your trip to Oak Brook. Then, pick a property that suits your budget, whether that's an economical stay or a lavish getaway.
- Decide how long to go for: Now that you're more familiar with Oak Brook, you can work out the perfect length of your holiday. Pull together a draft itinerary and allocate enough time for all the things you want to do.
- Combine your accommodation and airfare: After you've nailed down your trip dates and duration, lock in the right Oak Brook holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
