Pearl City Holidays from NZ$2,866

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The Latest Pearl City Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,767, price is now NZ$2,866 per person
NZ$2,866
per person
29 Oct - 5 Nov
found 11 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug. 2025

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$4,134, price is now NZ$3,085 per person
NZ$3,085
per person
29 Oct - 5 Nov
found 11 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug. 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,770, price is now NZ$4,323 per person
NZ$4,323
per person
29 Oct - 5 Nov
found 11 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$4,142, price is now NZ$3,126 per person
NZ$3,126
per person
29 Oct - 5 Nov
found 11 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was NZ$3,786, price is now NZ$2,934 per person
NZ$2,934
per person
29 Oct - 5 Nov
found 11 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
8.4/10 Very Good! (1,872 reviews)
Always love staying at The Palmer. The location is super convenient and the property oozes with Chicago charm. The staff is kind and always willing to help. Looking forward to my next stay.

Reviewed on 23 Aug. 2025

Pearl City Holiday

Our pick of the best Pearl City Hotel Deals

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

2.5 out of 5
Pearl City
The price is NZ$537 per night from 24 Aug to 25 Aug
NZ$537
24 Aug - 25 Aug
includes taxes & fees
Best stay
"Out of half a dozen or so cabin rentals, this one is the absolute best. It's clean, uncluttered, quiet, and huge! Water was hot, heater worked really well (it was a very cold week) and the kitchen worked well. Beds were comfy too. I can't say enough good things about this place!"

Reviewed on 5 Dec. 2024

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Savanna Inn & Suites

Savanna Inn & Suites

2 out of 5
101 Valley View Drive, Savanna, IL
Fully refundableReserve now, pay when you stay
The price is NZ$244 per night from 1 Sept to 2 Sept
NZ$244
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (898 reviews)
"The rooms were clean just a little outdated. The toilet handle needed to be held a while to make it flush. Loved that it was pet friendly and that it was right near nice places for hiking. If you’re visiting galena it’s a cheaper place to stay still relatively close by. Breakfast was the same on ..."

Reviewed on 5 Aug. 2025

Savanna Inn & Suites
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is NZ$148 per night from 21 Sept to 22 Sept
NZ$148
21 Sept - 22 Sept
includes taxes & fees
6.8/10 (334 reviews)
"Local"

Reviewed on 16 Aug. 2025

Super 8 by Wyndham Freeport
See all 106 properties in Pearl City
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 Pearl City holiday package cost?
You'll find cheap prices from NZ$2,866 on Expedia for your Pearl City escape. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your holiday to Pearl City costs.
What are the cheapest months to go to Pearl City?
If you'd like to snag a cheap Pearl City holiday package, consider planning a trip in January, February and November. You'll typically find lower rates on accommodation and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Pearl City?
The ideal duration for your Pearl City holiday depends on what you'd like to see. Generally, a few days to a week will give you enough time to check out all the top sights and explore some hidden gems along the way.
How to find the best Pearl City package deals?
Use Expedia's filters to help you find some tempting Pearl City package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Pearl City package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Pearl City holiday as a package?
You can enjoy significant savings on your Pearl City getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Pearl City?
If you're planning an impromptu Pearl City adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Pearl City?

  1. Choose your dates: What you plan to do in Pearl City and your preferred season can help you decide when to go.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Pearl City.
  3. Decide how long to go away for: Now that you're up to speed on Pearl City, you can figure out the right length of your holiday. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Pearl City holiday 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.