Oak Brook Vacations from AED2,500

Book a Hotel + Flight together to unlock savings

Photo by Judy Mahoney

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Oak Brook Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,269 reviews)
Beautiful space, right near the lake. Also has a cozy little restaurant on the 1st floor

Reviewed on 3 June 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,598 reviews)
This is the second time that we have stayed at the Trump hotel. It’s a beautiful property in a prime location. There are amazing views of the river and lake. The hotel is within walking distance of shopping, restaurants, and other fun sites! The spa is provides great service! I will definitely stay there again!

Reviewed on 1 June 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,754 reviews)
Our stay was ok. The hotel was not as updated as the pictures on the site shows. The carpets were stained and worn down, and the sheets and rooms were very old and outdated. The rooftop looked nothing like the photos. Otherwise it’s in a great location.

Reviewed on 31 May 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (1,733 reviews)
Location was great, walkable to anywhere in downtown Chicago, Millennium Park, Soldier Field, etc.

Reviewed on 27 May 2025

Find the Best Oak Brook Vacation Packages

Oak Brook Hotel Deals

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 AED 526 per night from Jul 3 to Jul 4
AED 526
AED 617 total
includes taxes & fees
3 Jul - 4 Jul
7.8/10 Good! (8,826 reviews)
"The facility has a great location in walking distance to many attractions. The family suite had a small bathroom with limited space."

Reviewed on 3 June 2025

Congress Plaza Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 490 per night from Jul 1 to Jul 2
AED 490
AED 575 total
includes taxes & fees
1 Jul - 2 Jul
9.2/10 Wonderful! (3,134 reviews)
"Nice clean hotel. Close to it all downtown"

Reviewed on 2 June 2025

citizenM Chicago Downtown
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 590 per night from Jun 29 to Jun 30
AED 590
AED 693 total
includes taxes & fees
29 Jun - 30 Jun
8.8/10 Excellent! (2,274 reviews)
"We stayed one night however all of the employees we had an interaction with were all very pleasant. The room was nice and comfortable. Desk staff were all very kind and helpful. The staff working outside by the door were very kind and helpful with questions we had about directions and ..."

Reviewed on 30 May 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,018 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 vacation package cost?
You’ll find cheap prices from AED2,500 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 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.

Discover the most popular places to visit in Oak Brook

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Wrigley Field is one of the more well-known attractions to visit during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.

Navy Pier
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(347 reviews)

Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.

Six Flags Great America