Oak Brook Vacation Packages

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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.

Top Oak Brook Vacation Deals

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

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on Jul. 16, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul. 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!

Reviewed on Jul. 16, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on Jul. 15, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

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 CA $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,979 reviews)
"The hotel is an old property, but the bedrooms were nicely renovated. The location is the highlight... nice views, close to everything, walkable distance to downtown and the lake."

Reviewed on Jul. 15, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $383 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,045 reviews)
"Very close to popular places."

Reviewed on Jul. 16, 2025

InterContinental Chicago Magnificent Mile by IHG
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 CA $199 per night from Aug 10 to Aug 11
CA $199
CA $234 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,444 reviews)
"clean...close to attractions.."

Reviewed on Jul. 14, 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,107 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Oak Brook

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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

What to do in Oak Brook

River tour boat in Chicago

Architecture River Tour

CA $67
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

CA $62
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

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Oak Brook

Frequently asked questions

How much does an Oak Brook vacation package cost?
You'll find cheap prices from CA $742 on Expedia for your Oak Brook break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Oak Brook costs.
What are the cheapest months to go to Oak Brook?
January, February and April are great times to search for cheap Oak Brook vacation packages. Opting to travel in quieter months means you can typically find lower prices on hotels and flights.
How many days is enough for Oak Brook?
Dedicate around 2 days for your Oak Brook vacation to take in everything that makes this place unique. Explore key neighbourhoods, including Yorkfield and York Centre. Then check out top attractions like Yorktown Shopping Centre and Galloping Ghost. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to venture outside of Oak Brook? Consider fitting in a day trip or two.
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'd like to check out attractions like Mayslake Peabody Mansion and Lizzadro Museum of Lapidary Art or take the road less travelled, you'll find plenty to keep you busy during your Oak Brook vacation.
How to find the best Oak Brook package deals?
Use Expedia's filter tool to find some tempting Oak Brook package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Oak Brook package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Oak Brook vacation as a package?
You can enjoy significant savings on your next Oak Brook getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Oak Brook?
If you're planning a spontaneous Oak Brook getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Oak Brook?

  1. Pick your travel dates: The things you'd like to do in Oak Brook and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Oak Brook. Then, choose a property that fits your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Oak Brook. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick an Oak Brook vacation package that brings all your bookings together.

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