Willowbrook Vacation Packages

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Your Willowbrook Vacation

Book a custom vacation package to Willowbrook and get ready for your next epic adventure. Consider basing yourself in the neighborhood of North Lawndale, which is great for golfing and walking, for a real taste of this interesting city. A trip to Willowbrook is an ideal opportunity to do a bit of sightseeing. Be sure to look around renowned attractions like Oakbrook Center Mall, Yorktown Shopping Center and Burr Ridge Village Center. Expedia is here to help you escape the everyday. Tailor your vacation to Willowbrook to suit your travel style, whatever that may be.

Top Willowbrook Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $907, price is now CA $673 per person
CA $673
per person
Sep 3 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Always a pleasure and a great location

Reviewed on Jun 24, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,665, price is now CA $1,113 per person
CA $1,113
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Muriel at the front desk made our 54th Anniversary memorable as she upgraded our room to a suite and sent a bottle of Prosecco and box of chocolates to our room plus a voucher for oysters at the restaurant. Kudos to her for being so kind and thoughtful. Thank you so much!!

Reviewed on Jun 30, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,076, price is now CA $779 per person
CA $779
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Nice hotel. Maybe I came at a bad time but there was way more many children than I expected. Not usually a problem but parents sucked and let their kids do whatever in areas with amenities. I paid for a late check out and had multiple house keeping staff knock to ask when I was checking out. Where is the communication in that department? Interior room will leave you with frosted windows and makes it feel a bit like a prison cell so I recommend upgrading for that city view

Reviewed on Jun 29, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,083, price is now CA $798 per person
CA $798
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good.

Reviewed on Jun 30, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was CA $1,045, price is now CA $806 per person
CA $806
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,323 reviews)
Staff were really helpful and sweet during check in. During checkout I was told there are no shuttles to take me to my terminal in quite a short and ubrupt manner. But to be honest the price is ridiculous for the outdated hotel. Seems like they think they can charge Hilton prices for what looks like a motel I the rooms just because they are the only hotel in the airport.

Reviewed on Jun 30, 2026

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Willowbrook 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 $211 per night from Jul 2 to Jul 3
CA $211
CA $251 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (10,175 reviews)
"In the 1980s and 1990s, I often stayed at this hotel when I went to Chicago for conferences or events at the Art Institute of Chicago. The location is still great for getting to the Art Institute (easy walking distance). Sadly, the hotel has become shabby. The bathroom in my unit appeared to have ..."

Reviewed on Jun 30, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,821 reviews)
"Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good."

Reviewed on Jun 30, 2026

Omni Chicago Hotel
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 $227 per night from Jul 6 to Jul 7
CA $227
CA $270 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,486 reviews)
"I booked three rooms at this hotel for a speacial occasion trip to celebrate a graduation. At check in I asked if one of the rooms could possibly have some kind of view of the city. I was quickly told it was not possible as the hotel was sold out. I was very sorry that out of the 100's of rooms in ..."

Reviewed on Jun 30, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,519 properties in Willowbrook
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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Stay near popular Willowbrook attractions

Creekside Park

8.2/10 (57 reviews)
After visiting Creekside Park, make a plan to see the other sights and activities in Willowbrook. You can attend a sporting event while in the area.
See properties

What to do in Willowbrook

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Willowbrook

Frequently asked questions

How much does a Willowbrook vacation package cost?
You can snap up a vacation package to this top destination from CA $673 on Expedia. However, how much your vacation to Willowbrook costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Willowbrook?
If you're hoping to book a cheap Willowbrook vacation package, consider visiting in December, January and February. You're likely to find better prices on airfares and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Willowbrook?
Allow around 2 days for your Willowbrook vacation if you want to immerse yourself in everything that makes this place unique. Explore key areas, including Clarendon Hills and Indian Head Park. Then check out major sights like Galloping Ghost and Mayslake Peabody Mansion. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to travel beyond Willowbrook? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Willowbrook?
Willowbrook is a good vacation destination with attractions like Willowbrook Community Park among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Willowbrook vacation promises fun for everyone.
How to find the best Willowbrook package deals?
Use Expedia's handy filters to help you find some fabulous Willowbrook package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Willowbrook package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Willowbrook vacation as a package?
You can enjoy significant savings on your next Willowbrook break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Willowbrook?
If you've got your Willowbrook vacation dates confirmed, book as early as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Willowbrook?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Willowbrook.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Willowbrook.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to experience in Willowbrook. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Willowbrook vacation package.

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