Willowbrook Holidays from NZ$3,873

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The Latest Willowbrook Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$4,297, price is now NZ$3,873 per person
NZ$3,873
per person
3 Aug - 6 Aug
found 15 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on 30 June 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,663, price is now NZ$5,321 per person
NZ$5,321
per person
3 Aug - 6 Aug
found 15 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The hotel is very clean Good air conditioning The staff is great The bar at the restaurant is very good The location is the best in Chicago Fancy neighborhood

Reviewed on 30 June 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,435, price is now NZ$3,900 per person
NZ$3,900
per person
3 Aug - 6 Aug
found 15 hours ago
Return flight included
Palmerston North (PMR) 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 June 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,523, price is now NZ$3,985 per person
NZ$3,985
per person
3 Aug - 6 Aug
found 15 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Nice clean room with minimalist/industrial vibe. Room was spacious. The front desk was helpful. The coffee shop was much appreciated.

Reviewed on 30 June 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was NZ$5,044, price is now NZ$4,520 per person
NZ$4,520
per person
3 Aug - 6 Aug
found 15 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Staff was super friendly. The room was perfect and the view was exceptional. Would definitely stay here again.

Reviewed on 27 June 2026

Willowbrook Holiday

Our pick of the best 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 NZ$312 per night from 2 July to 3 July
NZ$312
2 July - 3 July
includes taxes & fees
8/10 Very good! (10,181 reviews)
"Kind staff, loved the modern updates to the room. Daily housekeeping without even requesting! Will always stay here when i come to chicago."

Reviewed on 1 July 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 NZ$379 per night from 6 July to 7 July
NZ$379
6 July - 7 July
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 June 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 NZ$335 per night from 6 July to 7 July
NZ$335
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (4,474 reviews)
"Friendly staff. Our room was comfortable and clean."

Reviewed on 30 June 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,514 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

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$68
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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 NZ$3,873 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.