Willowbrook Holidays

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Willowbrook Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$662, price is now S$502 per person
S$502
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
Rooms were very old. There was blk mold or something in the shower. Window was broken too.

Reviewed on 1 Jul, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,019, price is now S$695 per person
S$695
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Very clean, great location. Every staff member we encountered was just terrific

Reviewed on 30 Jun, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,351, price is now S$982 per person
S$982
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was S$727, price is now S$539 per person
S$539
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,134 reviews)
Incredible location and staff so helpful and kind! Loved our stay

Reviewed on 30 Jun, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was S$956, price is now S$717 per person
S$717
per person
24 Sept - 26 Sept
found 1 hour ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,222 reviews)
Great experience! Thanks!

Reviewed on 29 Jun, 2026

Top hotels in Willowbrook

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 S$229 per night from 2 Jul to 3 Jul
S$229
2 Jul - 3 Jul
includes taxes & fees
8/10 Very good! (10,183 reviews)
"The place is very old and outdated. When entering it smells wet and dust from the start. The rooms are very wet and cold inside. Highly not recommended"

Reviewed on 1 Jul, 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 S$278 per night from 6 Jul to 7 Jul
S$278
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,823 reviews)
"Very clean, great location. Every staff member we encountered was just terrific"

Reviewed on 30 Jun, 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 S$262 per night from 6 Jul to 7 Jul
S$262
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (4,474 reviews)
"Friendly staff. Our room was comfortable and clean."

Reviewed on 30 Jun, 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.

Stay near popular Willowbrook attractions

Creekside Park

8.2/10 (57 reviews)
This serene area park features a natural creek alongside recreational courts and a playground. Enjoy a peaceful picnic by the water or challenge friends to a game of basketball in this local green space.
See properties

What to do in Willowbrook

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Willowbrook

Frequently asked questions

How much does a Willowbrook holiday package cost?
You can snap up a holiday package to this top destination from S$502 on Expedia. However, how much your holiday to Willowbrook costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Willowbrook?
If you'd like to score a cheap Willowbrook holiday package, consider planning a trip in December, January and February. You're likely to find lower prices on airfares and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Willowbrook?
Generally, a handful of days is enough to see the major sights during your Willowbrook holiday. But if you want to have more time to rest or take day trips, think about extending your trip.
Is it worth booking a holiday package to Willowbrook?
Willowbrook is a good holiday destination with attractions like Willowbrook Community Park among the many things to keep you entertained. Whether you're travelling with the family or planning a trip with friends, a Willowbrook holiday promises fun for everyone.
How to find the best Willowbrook package deals?
Bagging a cheap Willowbrook package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most affordable Willowbrook package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Willowbrook holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Willowbrook holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Willowbrook?
Score amazing discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Willowbrook holiday.
How to plan a trip to Willowbrook?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to holiday in Willowbrook.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may come up during your trip to Willowbrook.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Willowbrook. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the perfect Willowbrook holiday package for you.

Explore a world of travel with Expedia

* 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.