Oak Brook Trips (flight + hotel)

Photo by Judy Mahoney

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Top hotels in Oak Brook

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 P14,337 per night from Sep 7 to Sep 8
P14,337
P16,830 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (8,985 reviews)
"I love it"

Reviewed on Aug 5, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P9,900 per night from Aug 22 to Aug 23
P9,900
P13,049 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,833 reviews)
"Wonderful"

Reviewed on Aug 7, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P8,761 per night from Aug 24 to Aug 25
P8,761
P10,285 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (3,627 reviews)
"It was conveniently located downtown and within walking distance of the river, shopping, Millennium Park, and dining. Close to Subway to Wrigley Field and O’Hare."

Reviewed on Aug 6, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,292 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.

Popular places to visit

McCormick Place

McCormick Place

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
Millennium Park showing modern architecture, autumn leaves 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
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Oak Brook

River tour boat in Chicago

Architecture River Tour

P2,411
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

P2,617
per adult
98% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

P1,742
per adult
92% of travellers recommend
Skyline Lake Tour
See all activities in Oak Brook

Frequently asked questions

How much does an Oak Brook vacation 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 vacation 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 vacation packages and you could get some great off-season discounts.
How many days is enough for Oak Brook?
Oak Brook vacations 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 Center Mall and seek out some lesser-known spots. Don't skip neighborhoods such as Yorkfield and York Center 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 vacation package to Oak Brook?
Boasting a host of highlights starting with its amazing golfing, Oak Brook is a good vacation 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 vacation.
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 vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can personalize 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 vacation 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, favorite 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 vacation. Pull together a draft itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the right Oak Brook vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.