Hillsdale Holidays from NZ$3,234

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The Latest Hillsdale Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was NZ$4,009, price is now NZ$3,234 per person
NZ$3,234
per person
5 Sept - 11 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
It needs to be refreshed it’s drab and dreary and doesn’t look clean my bathroom was dangerous I don’t need a handicap accessible but there are no bars to hang on to getting in and out of shower just depressing and breakfast a joke 1 morning no protein at all

Reviewed on 13 July 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,324, price is now NZ$3,433 per person
NZ$3,433
per person
5 Sept - 11 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that looked a little tired and could use updating but overall we had a good sleep and were refreshed for the next day.

Reviewed on 13 July 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$4,833, price is now NZ$3,853 per person
NZ$3,853
per person
5 Sept - 11 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Well I thought I had a suite taco g the river but I only saw old fan boxes on top of buildings… I asked to switch rooms… they said there was an up charge which would’ve been fine but the more expensive room was mush smaller than the one facing the buildings…. Highly disappointed!! In addition.. there are no microwaves on the premises but there is a refrigerator … don’t make plans to bring back leftovers because there is NO WHERE to reheat them… for the money paid to stay here they lacked basic necessities..

Reviewed on 13 July 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was NZ$4,532, price is now NZ$3,677 per person
NZ$3,677
per person
5 Sept - 11 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (2,239 reviews)
Staff are wonderful. Room was nice. The “sofa” in the room was a piece of wood with cushions on it, not what I expected. The room was great size. Location is ideal for my girls trip.

Reviewed on 13 July 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,526, price is now NZ$3,710 per person
NZ$3,710
per person
5 Sept - 11 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
The bat was awesome!

Reviewed on 13 July 2026

Hillsdale Holiday

Our pick of the best Hillsdale Hotel Deals

DoubleTree by Hilton Davenport

DoubleTree by Hilton Davenport

4 out of 5
111 E 2nd St Davenport IA
The price is NZ$163 per night from 19 July to 20 July
NZ$163
19 July - 20 July
includes taxes & fees
7.8/10 Good! (1,023 reviews)
"Very friendly, efficient staff - Nathan was particularly fun. Room was clean, and breakfast had a wide variety of choices and quite delicious. Wish the second elevator was working, but we didn't have to wait too long for the one that was - just a bit crowded around check-out. We've stayed here twice, ..."

Reviewed on 14 July 2026

DoubleTree by Hilton Davenport
Wyndham Moline on John Deere Commons

Wyndham Moline on John Deere Commons

3.5 out of 5
1415 River Dr Moline IL
Fully refundableReserve now, pay when you stay
The price is NZ$199 per night from 26 July to 27 July
NZ$199
26 July - 27 July
includes taxes & fees
9/10 Wonderful! (1,256 reviews)
"great experience worth the monet"

Reviewed on 13 July 2026

Wyndham Moline on John Deere Commons
Isle Casino Hotel - Bettendorf

Isle Casino Hotel - Bettendorf

3 out of 5
1777 Isle Pkwy Bettendorf IA
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 9 Aug to 10 Aug
NZ$181
9 Aug - 10 Aug
includes taxes & fees
8.4/10 Very good! (1,013 reviews)
"Clean room with comfortable beds"

Reviewed on 14 July 2026

Isle Casino Hotel - Bettendorf
See all 346 properties in Hillsdale
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.

Frequently asked questions

How much does a Hillsdale holiday package cost?
Offering great value package deals from NZ$3,234 on Expedia, you'll be surprised at how little a holiday to Hillsdale costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Hillsdale?
You can typically find lower rates and greater availability in January, February and November. Take a look at our cheap Hillsdale holiday packages and you could land some excellent off-season deals.
How many days is enough for Hillsdale?
With a well-planned itinerary, you can easily tick off the most popular Hillsdale attractions in a handful of days. But if you'd like to venture off the beaten track or go on day trips, consider booking your Hillsdale holiday for longer.
How to find the best Hillsdale package deals?
Start your search for a Hillsdale package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor 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 Hillsdale package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsdale escape off to a flying start.
Is it cheaper to book a Hillsdale holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a personalised Hillsdale holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Hillsdale?
If you have your Hillsdale travel dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Hillsdale?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite season and the available activities will also help you decide when to visit Hillsdale.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Hillsdale.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Hillsdale. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodation and airfare: Once you've nailed down your travel dates and duration, book the right Hillsdale holiday package for you.

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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.