Pearl City Vacations from $344

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The Latest Pearl City vacation packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $615, price is now $344 per person
$344
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,473, price is now $537 per person
$537
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Price was $812, price is now $376 per person
$376
per person
Dec 16 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (146 reviews)
This is a beautiful property. The Getaway Restaurant

Reviewed on Oct 15, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $681, price is now $349 per person
$349
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Favorite place to stay

Reviewed on Oct 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,623, price is now $883 per person
$883
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Great staff extremely friendly and helpful.

Reviewed on Oct 15, 2025

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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
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

Get rates
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
$129 nightly
The price is $143 total per night from Oct 16 to Oct 17
$143 total
Oct 16 - Oct 17
Total with taxes and fees
9/10 Wonderful! (925 reviews)
"A+. Rex was great"

Reviewed on Sep 23, 2025

Savanna Inn & Suites
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
$118 nightly
The price is $131 total per night from Oct 26 to Oct 27
$131 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (826 reviews)
"Clean room, breakfast was good. Staff was nice."

Reviewed on Oct 14, 2025

Country Inn & Suites by Radisson, Freeport, IL
See all 105 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.

Pearl City Essential Information

Language
English
Currency
U.S dollars
Population
810
Top Sights
Lake Le Aqua Na State Park, Freeport Art Museum and Silver Creek Museum

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Frequently asked questions

How much does a Pearl City vacation package cost?
You'll find cheap prices from $344 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?
August, September and December are great times to search for cheap Pearl City vacation packages. Choosing to travel in quieter periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Pearl City?
The ideal length of your Pearl City vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to visit all the main attractions and explore some hidden spots 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.
Does Expedia offer Book Now, Pay Later Pearl City vacation packages?
Jet off on your dream trip to Pearl City with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next paycheck — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up bargains while they last.

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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.