Pearl City Vacations from $302

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The Latest Pearl City vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $516, price is now $302 per person
$302
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was spotless & staff were courteous

Reviewed on Dec 16, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $619 per person
$619
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $546, price is now $342 per person
$342
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️

Reviewed on Dec 16, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $613, price is now $386 per person
$386
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $582, price is now $371 per person
$371
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 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 IL
$254 nightly
The price is $280 total per night from Dec 18 to Dec 19
$280 total
Dec 18 - Dec 19
Total with taxes and fees
10/10 Exceptional! (3 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
$106 nightly
The price is $118 total per night from Jan 8 to Jan 9
$118 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8.8/10 Excellent! (847 reviews)
Friendly, helpful staff, delicious coffee, Cookies in the lobby, a great full breakfast with lots of warm and easy-to-grab options, microwave in the room. We’ve stayed twice and enjoyed it b

Reviewed on Dec 9, 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
$81 nightly
The price is $90 total per night from Dec 29 to Dec 30
$90 total
Dec 29 - Dec 30
Total with taxes and fees
7.8/10 Good! (709 reviews)
Stayed for a night, i must say the stay is nice. The place needs updating. Not today but in the future.

Reviewed on Nov 28, 2025

Baymont by Wyndham Freeport
See all 117 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.

Find the Best Pearl City Vacation Packages

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 $302 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.