Pearl City Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Pearl City Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,221, price is now CA $812 per person
CA $812
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay.

Reviewed on Jul 18, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,336, price is now CA $945 per person
CA $945
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
Great experience the staff was super friendly and the hotel location was just amazing right in downtown Chicago. I will definitely be staying there again..

Reviewed on Jul 18, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $3,157, price is now CA $2,244 per person
CA $2,244
per person
Oct 8 - Oct 12
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very pleasant room

Reviewed on Jul 18, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,641, price is now CA $1,175 per person
CA $1,175
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (135 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,169, price is now CA $1,554 per person
CA $1,554
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Level hotels are awesome

Reviewed on Jul 18, 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!

Pearl City IL
The price is CA $122 per night from Jul 21 to Jul 22
CA $122
CA $476 total
Jul 21 - Jul 22
includes taxes & fees
10/10 Exceptional! (4 reviews)
"This is such a great place! It was perfect for our family of 4. Our 14 and 12 year old loved the loft space, and my husband and I were super comfy in the bedroom. The lower level was great for family time in the evening, and where we all hung out at the end of the day. The property surrounding was ..."

Reviewed on Jun 21, 2026

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
The price is CA $181 per night from Jul 20 to Jul 21
CA $181
CA $201 total
Jul 20 - Jul 21
includes taxes & fees
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
The price is CA $167 per night from Aug 2 to Aug 3
CA $167
CA $185 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (914 reviews)
"Staff was very pleasant and helpful"

Reviewed on Jul 13, 2026

Country Inn & Suites by Radisson, Freeport, IL
See all 123 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
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Family Vacations
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Frequently asked questions

How much does a Pearl City vacation package cost?
You can pick up a vacation package to this destination from CA $812 on Expedia. However, how much your vacation to Pearl City costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Pearl City?
January, February and November are great times to look for cheap Pearl City vacation packages. Choosing to travel in quieter months means you can generally find better prices on hotels and flights.
How many days is enough for Pearl City?
The ideal length for your Pearl City vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you plenty of time to go to all the leading sights and explore some hidden spots along the way.
How to find the best Pearl City package deals?
Use Expedia's handy filters to find some unbeatable Pearl City package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Pearl City package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Pearl City vacation as a package?
You can enjoy significant savings on your Pearl City retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pearl City?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Pearl City trip.
How to plan a trip to Pearl City?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Pearl City.
  2. Set a budget: Consider costs such as flights, food and transportation when working out how much to set aside for your trip to Pearl City. Then, select a hotel that suits your budget, whether that's an affordable option or a deluxe getaway.
  3. Decide how long to go away for: Now that you're up to speed on Pearl City, you can work out the right length of your vacation. Pull together a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Pearl City vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.