Oak Brook Holidays

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Oak Brook Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
1 May - 4 May
found 1 day ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
8.8/10 Excellent! (1,967 reviews)
It was a beautiful property.

Reviewed on 20 Mar,2025

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
per person
1 May - 4 May
found 1 day ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
9.2/10 Wonderful! (1,585 reviews)
So, I’ve booked the Kinzie before (maybe 2 years ago if so) to celebrate my husbands birthday (staycation) and we were blown away by everything, they even upgraded us for being a VIP on Expedia. This time, horrible. First of they don’t tell you they are doing renovations, which is ok, but the hostess has a very small desk, nothing fancy. It looks like it’s all kind of put together last minute, and that includes the rooms as well. The cleanliness 5/10. The vents were dirty, the bathroom was not properly clean, the showier curtains were so so. It looked like they went to hobby lobby and bought anything that looked like “hotel vibes”. The view of our room was a wall (no one said anything about it- and whenever we asked the host if they were doing room renovations he said no, that those are the normal rooms and they’re been like that since always, which is a lie because I’ve been there before and they have 0 comparison). Overall it was not the best experience and I won’t be staying here anymore.

Reviewed on 20 Mar,2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
1 May - 4 May
found 1 day ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Our stay was great, the staff was amazing. Highly recommended.

Reviewed on 20 Mar,2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
1 May - 4 May
found 1 day ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
9/10 Wonderful! (1,036 reviews)
Nothing unique but it was nice and we enjoyed it. Tre room decors was really cool. Not what you’d expect

Reviewed on 18 Mar,2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
1 May - 4 May
found 1 day ago
Return direct flight included
San Francisco (SFO) to Chicago (ORD)
9/10 Wonderful! (1,595 reviews)
Staff was very friendly. Rooms were super nice for the price. The location was perfect to everything around. Side note the music selection in the lobby was on point.

Reviewed on 21 Mar,2025

Top hotels in Oak Brook

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$154 per night from 20 Apr to 21 Apr
S$154
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (3,914 reviews)
"the elevator was very slow the whole time there"

Reviewed on 18 Mar,2025

River Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$256 per night from 23 Mar to 24 Mar
S$256
includes taxes & fees
23 Mar - 24 Mar
9.6/10 Exceptional! (1,902 reviews)
"The location is perfect. Almost right on Riverwalk and Magnificent Mile. Some of the staff was not always professional. The carpet in the common areas were not clean and gave out a foul smell. However, the rooms were clean and housekeeping did a good job. Not a bad experience for the price."

Reviewed on 18 Mar,2025

L7 Chicago by LOTTE
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$218 per night from 20 Apr to 21 Apr
S$218
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,001 reviews)
"Friendly staff and spacious room. Easy check-in"

Reviewed on 17 Mar,2025

The Westin Michigan Avenue Chicago
See all 4,740 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 S$658 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.

Popular places to visit

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

Wrigley Field

4.5/5(40 reviews)

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

4.5/5(36 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
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

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

Flyover in Chicago

Flyover in Chicago

S$51
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$66
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$60
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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. 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.