Oak Brook Holidays from AU$11,449

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Your Oak Brook Holiday

With all your travel plans organised before you head off, our Oak Brook holiday packages mean you can simply focus on having a good time! One neighbourhood to consider staying in this lively city is North Lawndale, which is good for golfing and walking. Ready to get out and explore? Brookfield Zoo, Oakbrook Centre Mall and Morton Arboretum are three of the best places to visit during a trip to Oak Brook. No matter your travel plans or budget, organising a tailored Oak Brook holiday is simple with Expedia.

The Latest Oak Brook Holiday Deals

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$12,965, price is now AU$11,449 per person
AU$11,449
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$15,480, price is now AU$12,493 per person
AU$12,493
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
This is a truly luxurious hotel. I highly recommend it. You can not find a better hotel in Chicago

Reviewed on 20 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$14,165, price is now AU$11,966 per person
AU$11,966
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug. 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was AU$13,264, price is now AU$11,759 per person
AU$11,759
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,071 reviews)
A very nice small boutique hotel

Reviewed on 19 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$12,980, price is now AU$11,544 per person
AU$11,544
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug. 2025

Oak Brook Holiday

Oak Brook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
8,100
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Rosemont Theatre, Brookfield Zoo and Parkway Bank Park Entertainment District

Our pick of the best Oak Brook Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$273 per night from 1 Sept to 2 Sept
AU$273
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug. 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$340 per night from 14 Sept to 15 Sept
AU$340
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,985 reviews)
"Nice view"

Reviewed on 23 Aug. 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$275 per night from 3 Sept to 4 Sept
AU$275
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,219 properties in Oak Brook
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Oak Brook

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Oak Brook

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Oak Brook

Frequently asked questions

How much does an Oak Brook holiday package cost?
You'll find cheap prices from AU$11,449 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?

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