Oak Brook Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Oak Brook Vacation Packages

Oak Brook Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 672 per night from Aug 7 to Aug 8
SARĀ 672
SARĀ 766 total
7 Aug - 8 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 540 per night from Jul 19 to Jul 20
SARĀ 540
SARĀ 643 total
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very Good! (1,768 reviews)
"Disappointing Service & Zero Accountability Trying to get in touch with this property ahead of time was incredibly frustrating. I called multiple times over several days and was never able to reach anyone, nor did the calls ever go to a voicemail system. When I checked in, I politely shared this ..."

Reviewed on 17 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 SARĀ 1,115 per night from Aug 3 to Aug 4
SARĀ 1,115
SARĀ 1,326 total
3 Aug - 4 Aug
includes taxes & fees
The Wade
See all 4,975 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.

Stay near popular Oak Brook attractions

A golf course with a large tree in the foreground, a pond, and a clear sky.

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.
See properties

Frequently asked questions

How much does an Oak Brook vacation package cost?
You'll find cheap prices on Expedia for your Oak Brook break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Oak Brook costs.
What are the cheapest months to go to Oak Brook?
January, February and April are great times to search for cheap Oak Brook vacation packages. Opting to travel in quieter months means you can typically find lower prices on hotels and flights.
How to find the best Oak Brook package deals?
Use Expedia's filter tool to find some tempting Oak Brook package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Oak Brook package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Oak Brook vacation as a package?
You can enjoy significant savings on your next Oak Brook getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Oak Brook?
If you're planning a spontaneous Oak Brook getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Oak Brook?

  1. Pick your travel dates: The things you'd like to do in Oak Brook and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Oak Brook. Then, choose a property that fits your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Oak Brook. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick an Oak Brook vacation package that brings all your bookings together.