Title: Pearl City Vacation Packages & Trips 2026 from CA $843 | Expedia.ca

[Hotels in Pearl City](https://expedia.ca/Pearl-City-Hotels.d3000434968.Travel-Guide-Hotels)[Vacation Rentals in Pearl City](https://expedia.ca/Pearl-City-Vacation-Rentals.d3000434968.Travel-Guide-VacationRentals)[Pearl City Car Rentals](https://expedia.ca/Car-Rentals-In-Pearl-City.d3000434968.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Pearl City Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Pearl City Vacation Deals

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

![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fairmont Chicago at Millennium Park

Downtown Chicago

CA $843

per person

May 17 - May 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (2,076 reviews)

Everything was perfect

Reviewed on Mar 26, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,020

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer. Buffet breakfast is included and that makes it very good value. Hotel also has a gym/ Not too many amenities in the room though.

Reviewed on Apr 2, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,017

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

This hotel provides the basics no amenities you have to pay extra for breakfast and any amenities you would like.

Reviewed on Apr 3, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,244

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (421 reviews)

Garage area very dark and unsafe

Reviewed on Mar 31, 2026

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $1,143

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,140 reviews)

Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back.

Reviewed on Mar 23, 2026

## Ready to book your vacation to Pearl City?

Choose your dates

## Pearl City Hotel Deals

![The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!](https://images.trvl-media.com/lodging/107000000/106690000/106680700/106680635/225f4161_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

 Pearl City IL

CA $132

CA $444 total

Apr 4 - Apr 5

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=106680635&PinnedHotelID=106680635&HadPinnedHotel=true&regionId=3000434968)

![Country Inn & Suites by Radisson, Freeport, IL](https://images.trvl-media.com/lodging/1000000/30000/28000/27974/9cdfac50_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Country Inn & Suites by Radisson, Freeport, IL

1710 South Dirck Drive Freeport IL

Fully refundable

CA $157

CA $174 total

Apr 5 - Apr 6

includes taxes & fees

9/10 Wonderful! (876 reviews)

Convenient and safe location

Reviewed on Apr 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=27974&PinnedHotelID=27974&HadPinnedHotel=true&regionId=3000434968)

![Hampton Inn Freeport](https://images.trvl-media.com/lodging/2000000/1640000/1632400/1632362/319dd9f0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn Freeport

109 S Galena Ave Freeport IL

Fully refundableReserve now, pay when you stay

CA $142

CA $157 total

Apr 19 - Apr 20

includes taxes & fees

8.8/10 Excellent! (461 reviews)

The breakfast was excellent. The place was clean. And the staff was very helpful.

Reviewed on Mar 30, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=1632362&PinnedHotelID=1632362&HadPinnedHotel=true&regionId=3000434968)

[See all 122 properties in Pearl City](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&regionId=3000434968)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## 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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app