Oak Brook Holidays from NZ$1,675

Book a Hotel + Flight or Car together to unlock savings

Photo by Judy Mahoney

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Oak Brook Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
8.2/10 Very Good! (1,766 reviews)
Property was nice and clean today

Reviewed on 25 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Honestly one of the best places to stay at. Really loved this place.

Reviewed on 26 Jun. 2025

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
Great location. Nice rooms

Reviewed on 22 Jun. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Very comfortable hotel. Very responsive staff.

Reviewed on 25 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun. 2025

Oak Brook Holiday

Our pick of the best Oak Brook Hotel Deals

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 NZ$318 per night from 29 June to 30 June
NZ$318
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (4,263 reviews)
"Na"

Reviewed on 25 Jun. 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is NZ$358 per night from 1 July to 2 July
NZ$358
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (1,920 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on 24 Jun. 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$263 per night from 6 July to 7 July
NZ$263
6 July - 7 July
includes taxes & fees
8.8/10 Excellent! (2,337 reviews)
"Very spacious & clean rooms. Great service, friendly staff & perfect location!!"

Reviewed on 25 Jun. 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,020 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.

Frequently asked questions

How much does an Oak Brook holiday package cost?
You'll find cheap prices from NZ$1,675 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.

Discover the most popular places to visit in Oak Brook

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Oak Brook

River tour boat in Chicago

Architecture River Tour

NZ$81
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$75
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

NZ$74
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Oak Brook
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.