Oak Brook Vacations from $264

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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.

The Latest Oak Brook vacation packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (366 reviews)
Staff was friendly. Beaches very clean and relaxing. Rooms were nice. Had a great experience. Will do it again.

Reviewed on Aug 14, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on Aug 16, 2025

The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
Downtown Kenosha
Save 100% on your flight
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
9.4/10 Exceptional! (1,007 reviews)
Reasonable price. It's in walking distance to the harbor and various eateries such as the ice cream parlor across the street. I would definitely recommend this hotel to family and friends visiting downtown Kenosha.

Reviewed on Aug 9, 2025

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 16 - Sep 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
It was a great experience and the hotel is right in the heart of downtown and walking distance to a lot of different things. Best thing is the staff they are extremely nice and try’s to accommodate as much as they able to. One of the more affordable options in downtown. I would say the only negative thing are the rooms they are extremely small and not good for a family with small kids it’s very crammed. Otherwise would come back with me and the wife.

Reviewed on Aug 16, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (431 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 2025

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Discover the most popular places to visit in Oak Brook

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Oak Brook

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oak Brook

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
$161 nightly
The price is $189 total per night from Sep 1 to Sep 2
$189 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,982 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

Reviewed on Aug 14, 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
$198 nightly
The price is $229 total per night from Sep 4 to Sep 5
$229 total
Sep 4 - Sep 5
Total includes taxes and fees
8.4/10 Very Good! (1,856 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on Aug 13, 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
$152 nightly
The price is $179 total per night from Aug 25 to Aug 26
$179 total
Aug 25 - Aug 26
Total includes taxes and fees
8.4/10 Very Good! (3,690 reviews)
"I like how the room i had was clean and the bed i comfy. I didn't like how there are people outside the hotel peddling for change and cigarettes. It feels unsafe for out-of-towners like me."

Reviewed on Aug 16, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,189 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.

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Frequently asked questions

How much does an Oak Brook vacation package cost?
You'll find cheap prices from $264 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 generally find reduced prices and greater availability in December, January and February. Explore our cheap Oak Brook vacation packages and you could land some great off-season discounts.
How many days is enough for Oak Brook?
Oak Brook vacations can be short or long, but to get a real feel for this place, we'd suggest 2 days is a good ballpark. With this timeframe, you can visit major attractions like Mayslake Peabody Mansion and Oakbrook Center Mall as well as underrated spots. Don't forget to explore cool areas such as Yorkfield and York Center either. If you're clever with your time, you may even be able to take a day trip or two from Oak Brook too.
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 want to explore sights such as Oakbrook Center Mall and Oak Brook Golf Course or take the path less traveled, you'll find loads to see and do on 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 your travel dates: The things you want to do in Oak Brook and your preferred season will help you decide when to travel.
  2. Budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Oak Brook.
  3. Explore Oak Brook using Expedia's trip planning tool: Gain insights into the most popular attractions and best hotels for your trip to Oak Brook. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
  4. Set the duration of your trip: Start by compiling a list of the attractions you want to experience in Oak Brook. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Oak Brook vacation package.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on Oak Brook's best offerings. Find all the exciting things to do in Oak Brook with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Oak Brook vacation packages?
Your Oak Brook trip is meant to be a relaxing escape from your busy life, not a reason for money worries. So to give you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.