Pearl City Vacations from ￥244,466

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The Latest Pearl City Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 16 - Sep 22
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on Jul 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Beautiful and upscale property

Reviewed on Jul 17, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun 13, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on Jul 16, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul 15, 2025

Find the Best Pearl City Vacation Packages

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 ￥17,730 per night from Jul 21 to Jul 22
￥17,730
￥51,850 total
Jul 21 - Jul 22
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 Dec 5, 2024

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
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 ￥12,125 per night from Jul 27 to Jul 28
￥12,125
￥13,456 total
Jul 27 - Jul 28
includes taxes & fees
6.8/10 (326 reviews)
hotel clerk very nice and helpful
"the room was very nice and the hotel clerk was very nice and she was very helpful"

Reviewed on Jul 13, 2025

Super 8 by Wyndham Freeport
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is ￥13,449 per night from Aug 17 to Aug 18
￥13,449
￥14,927 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (662 reviews)
"We had a good stay with decent breakfast choices."

Reviewed on Jul 14, 2025

Baymont by Wyndham Freeport
See all 108 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 vacation package cost?
You'll find cheap prices from ￥244,466 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 vacation to Pearl City costs.
What are the cheapest months to go to Pearl City?
If you'd like to snag a cheap Pearl City vacation package, consider planning a trip in January, February and November. You'll typically find lower rates on accommodations and flights during these months --- perfect for budget-conscious travelers.
How many days is enough for Pearl City?
The ideal duration for your Pearl City vacation 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 vacation package as soon as possible.
Is it cheaper to book a Pearl City vacation as a package?
You can enjoy significant savings on your Pearl City getaway by booking a personalized vacation 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 vacation 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 vacation. 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 vacation 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.