Oak Brook Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Oak Brook Vacation
Come and discover this fascinating city for yourself with a Oak Brook vacation package. Consider spending some time in the neighborhood of North Lawndale, which is great for golfing and walking, and your time here is bound to be unforgettable. Brookfield Zoo, Morton Arboretum and Oakbrook Center Mall are just some of the many attractions worth exploring during your trip to Oak Brook. Expedia will help you escape your routine. Tailor your vacation to Oak Brook to match your travel style, whatever that may look like.
Top Oak Brook Vacation Deals
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
CA $1,030
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Staff very helpful and friendly.
Room size great and had what was needed for my 1 night stay. Shower was temperamental in the morning for hot water.
Reviewed on Sep 21, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,119
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel
Reviewed on Sep 21, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,508
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 2026
Ready to book your vacation to Oak Brook?
Oak Brook Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $255
CA $303 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,454 reviews)
"Too expensive for nothing. Even the keys need to be made ourselves and not by the staff. Hostel kind of feel at luxury hotel prices."
Reviewed on Sep 21, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $258
CA $307 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (10,177 reviews)
"Beautiful building and a great stay. I had a lake view room and this was my second time staying here!"
Reviewed on Sep 21, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $250
CA $298 total
Oct 13 - Oct 14
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)
Enjoy a round of golf in Oak Brook at Oak Brook Golf Course. Stroll along the riverfront or attend a sporting event in this family-friendly area.
Photo by Judy Mahoney
Graue Mill and Museum
8.4/10 (94 reviews)
You can spend time browsing the exhibits at Graue Mill and Museum during your trip to Oak Brook. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Oakbrook Center Mall
9.2/10 (585 reviews)
You can enjoy retail therapy at Oakbrook Center Mall during your visit to Oak Brook. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Mayslake Peabody Mansion
8.2/10 (92 reviews)
Learn about the local history of Oak Brook with a stop at Mayslake Peabody Mansion. While you're here, you can savor the top-notch restaurants.
Lizzadro Museum of Lapidary Art
8.2/10 (74 reviews)
You can spend an afternoon exploring the galleries in Lizzadro Museum of Lapidary Art during your trip to Oak Brook. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
What to do in Oak Brook
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Frequently asked questions
How much does an Oak Brook vacation package cost?
You'll find cheap prices from CA $1,030 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 many days is enough for Oak Brook?
Dedicate around 2 days for your Oak Brook vacation to take in everything that makes this place unique. Explore key neighbourhoods, including Yorkfield and York Centre. Then check out top attractions like Yorktown Shopping Centre and Galloping Ghost. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to venture outside of Oak Brook? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Oak Brook?
Boasting a host of highlights starting with its top-notch golfing, Oak Brook is a good vacation destination. Whether you'd like to check out attractions like Mayslake Peabody Mansion and Lizzadro Museum of Lapidary Art or take the road less travelled, you'll find plenty to keep you busy during your Oak Brook vacation.
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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
