Pearl City Vacation Packages
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Top Pearl City Vacation Deals
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
La Banque Hotel
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Aloft Chicago Downtown River North
Downtown Chicago
Price was CA $1,064, price is now CA $778 per person
CA $778
per person
Mar 31 - Apr 4
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Room and customer service was great!
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,209, price is now CA $885 per person
CA $885
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was friendly, and room was cleaned well. Free breakfast was also a nice touch and better than expected
Reviewed on Feb 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,950, price is now CA $1,433 per person
CA $1,433
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pearl City Hotel Deals
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Pearl City IL
The price is CA $121 per night from Feb 24 to Feb 25
CA $121
CA $429 total
Feb 24 - Feb 25
includes taxes & 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
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $133 per night from Mar 8 to Mar 9
CA $133
CA $147 total
Mar 8 - Mar 9
includes taxes & fees
8.8/10 Excellent! (861 reviews)
Staff friendly and helpful. even opened the pool for our family and granddaughters, which had been temporaily closed.
Reviewed on Jan 26, 2026
Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Feb 15 to Feb 16
CA $128
CA $142 total
Feb 15 - Feb 16
includes taxes & fees
8.6/10 Excellent! (454 reviews)
Nice clean room. Staff was friendly. Breakfast was good with lots of options. Stayed here last year for a tumbling competition and we loved it so we stayed here again for the competition.
Reviewed on Feb 2, 2026
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.
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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.
