Pearl City Vacation Packages

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Top Pearl City Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago - Glenview, an IHG Hotel

Staybridge Suites Chicago - Glenview, an IHG Hotel

3 out of 5
per person
May 1 - May 6
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Quiet, Breakfast was good, It was a quick stay.

Reviewed on Mar. 2, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 1 - Jun. 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
A fun, classy, and unique hotel that doesn't take itself overly seriously, so you really get to enjoy yourself. In the heart of the loop nearby to the Bean, State St., Michigan Ave and many of Chicago's most iconic landmarks. Staff was super chill and courteous. For history and architecture buffs, this place is first claas.

Reviewed on Mar. 3, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (287 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on Jan. 20, 2025

The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
May 1 - May 6
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
Loved this property!!

Reviewed on Feb. 22, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr. 28 - May 2
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service. Beautiful room. Great location.

Reviewed on Mar. 4, 2025

Ready to book your vacation to Pearl City?

 

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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 CA $141 per night from Mar. 9 to Mar. 10
CA $141
CA $464 total
includes taxes & fees
Mar 9 - Mar 10
10/10 Exceptional! (2 reviews)
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!
Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Freeport, IL
2.5 out of 5
1710 South Dirck Drive, Freeport, IL
Fully refundable
The price is CA $159 per night from Mar. 23 to Mar. 24
CA $159
CA $177 total
includes taxes & fees
Mar 23 - Mar 24
8.8/10 Excellent! (763 reviews)
"Room had a funky smell, seemed clean unless you looked into corners or behind furniture etc. bed was comfortable, shower had great water pressure."

Reviewed on Mar. 4, 2025

Country Inn & Suites by Radisson, Freeport, IL
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 CA $98 per night from Mar. 17 to Mar. 18
CA $98
CA $108 total
includes taxes & fees
Mar 17 - Mar 18
8/10 Very Good! (616 reviews)
Comfortable. Could have been cleaner.
"The beds were very comfortable. Comfort and cleanliness are my top priority. This room could have been cleaner. There was a lot of wear and tear on the carpet, desk chair, bathroom walls and carpet. The desk chair had rips on the seat material. The bathroom wall behind the door was dirty. There were ..."

Reviewed on Feb. 28, 2025

Baymont by Wyndham Freeport
See all 107 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Pearl City vacation package cost?
You’ll find cheap prices from CA $623 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.