Pearl City Vacations from $301

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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 $500, price is now $301 per person
$301
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast options had a variety of foods available and the orange juice seemed very fresh.

Reviewed on Jan 19, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was $1,719, price is now $904 per person
$904
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $932, price is now $502 per person
$502
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $627, price is now $387 per person
$387
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
no the room was dirty and smell musty

Reviewed on Jan 18, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $677, price is now $418 per person
$418
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!

Reviewed on Jan 10, 2026

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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
$260 nightly
The price is $287 total per night from Jan 20 to Jan 21
$287 total
Jan 20 - Jan 21
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
Fully refundable
$100 nightly
The price is $111 total per night from Feb 2 to Feb 3
$111 total
Feb 2 - Feb 3
Total with taxes and fees
8.8/10 Excellent! (857 reviews)
Clean staff very courteous

Reviewed on Jan 13, 2026

Country Inn & Suites by Radisson, Freeport, IL
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $116 total per night from Feb 6 to Feb 7
$116 total
Feb 6 - Feb 7
Total with taxes and fees
8.6/10 Excellent! (452 reviews)
pool was nice, friendly staff,

Reviewed on Dec 29, 2025

Hampton Inn Freeport
See all 119 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 $301 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.