Oak Brook Holidays

Photo by Judy Mahoney

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Top hotels in Oak Brook

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 S$228 per night from 3 Sept to 4 Sept
S$228
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very Good! (1,226 reviews)
"It was very close to navy pier where it was just a 10 min way. And had a great view from our room. Facing the lake"

Reviewed on 27 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 S$297 per night from 15 Sept to 16 Sept
S$297
15 Sept - 16 Sept
includes taxes & fees
7.8/10 Good! (9,016 reviews)
"I really enjoyed my stay here . The hotel is very historical and is known for hosting beautiful weddings, it’s huge , restaurants on property, and is very close to everything there is to see in downtown Chicago . Very close to the river walk , millennium park, coffee shops/breakfast, the loop , Taco ..."

Reviewed on 25 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 S$230 per night from 3 Sept to 4 Sept
S$230
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,774 reviews)
"The staff were very accommodating and nice. The rooms were spacious and comfortable."

Reviewed on 24 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.

Popular places to visit

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

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
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 which includes modern architecture, a city and autumn leaves

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

What to do in Oak Brook

River tour boat in Chicago

Architecture River Tour

S$53
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

S$52
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

S$58
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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.