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Prince Edward Island

$509+ Cheap flights from Chicago (CHI) to Prince Edward Island

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from Chicago to Prince Edward Island

Cheapest flights from Chicago to Prince Edward Island
Explore the most affordable flight options available from Chicago to Prince Edward Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:00 amORD - YYG
1 stop5h 40mAir Canada
Thu 12/185:05 amYYG - ORD
1 stop9h 56mAir Canada
Deal found 12/3$705
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:00 amORD - YYG
1 stop5h 40mAir Canada
Fri 12/195:05 amYYG - ORD
1 stop12h 05mAir Canada
Deal found 12/3$777
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:00 amORD - YYG
1 stop7h 50mAir Canada
Wed 12/1711:15 amYYG - ORD
1 stop5h 40mAir Canada
Deal found 12/3$864
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/153:55 pmORD - YYG
1 stop6h 25mAir Canada
Wed 12/1711:15 amYYG - ORD
1 stop5h 40mAir Canada
Deal found 12/3$881
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:00 amORD - YYG
1 stop7h 50mAir Canada
Thu 12/185:05 amYYG - ORD
1 stop9h 56mAir Canada
Deal found 12/3$890
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/153:55 pmORD - YYG
1 stop6h 25mAir Canada
Thu 12/185:05 amYYG - ORD
1 stop16h 40mAir Canada
Deal found 12/3$908
This United Airlines deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:00 amORD - YYG
1 stop5h 40mUnited Airlines
Thu 12/1811:15 amYYG - ORD
2 stops12h 24mUnited Airlines
Deal found 12/3$955
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:00 amORD - YYG
1 stop7h 50mAir Canada
Fri 12/195:05 amYYG - ORD
1 stop16h 40mAir Canada
Deal found 12/3$962
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:55 pmORD - YYG
1 stop6h 25mAir Canada
Thu 1/15:05 amYYG - ORD
1 stop12h 05mAir Canada
Deal found 12/3$963
This Air Canada deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:05 amORD - YYG
2 stops8h 35mAir Canada
Fri 12/195:05 amYYG - ORD
1 stop16h 40mAir Canada
Deal found 12/3$971
This FlightHub deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/154:15 pmMDW - YYG
2 stops18h 47mPorter Airlines
Wed 12/171:45 pmYYG - MDW
2 stops22h 20mPorter Airlines
Deal found 12/3$1,128
This FlightHub deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:00 amMDW - YYG
2 stops24h 02mPorter Airlines
Thu 1/11:45 pmYYG - MDW
2 stops22h 20mPorter Airlines
Deal found 12/3$1,164

Find flight deals from Chicago to Prince Edward Island

Keep the following information in mind while searching for Chicago to Prince Edward Island flight deals. Data was last updated December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$509
(Air Canada)
Provider with most accurate pricing for Chicago (CHI)-Charlottetown flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Charlottetown flights.
Search Deals
From Chicago (CHI) to Prince Edward Island
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Prince Edward Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 4, 2025.
Use the filters below to find and compare flights from Chicago to Prince Edward Island that are best for you.

Fly from

Chicago

Fly to

Prince Edward Island

Route

Depart

Return

Price

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 1/15

10:00 am-5:40 pm

1 stop5h 40m

Charlottetown

Sun 1/18

11:15 am-2:55 pm

1 stop5h 40m

$509

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 1/18

10:00 am-5:40 pm

1 stop5h 40m

Charlottetown

Tue 1/20

11:15 am-2:55 pm

1 stop5h 40m

$509

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 1/17

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Tue 1/20

11:15 am-2:55 pm

1 stop5h 40m

$509

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 1/15

10:00 am-5:40 pm

1 stop5h 40m

Charlottetown

Tue 1/20

11:15 am-2:55 pm

1 stop5h 40m

$509

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 1/17

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Mon 1/19

11:15 am-2:55 pm

1 stop5h 40m

$509

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 1/29

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Fri 1/30

11:15 am-2:55 pm

1 stop5h 40m

$509

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Mon 1/26

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Tue 1/27

5:05 am-9:13 am

1 stop6h 08m

$512

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 1/29

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Sat 1/31

5:05 am-9:15 am

1 stop6h 10m

$512

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 1/30

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Sat 1/31

5:05 am-9:15 am

1 stop6h 10m

$512

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 1/24

8:00 am-5:50 pm

1 stop7h 50m

Charlottetown

Sun 1/25

5:05 am-9:13 am

1 stop6h 08m

$512

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 19 results
1
2

Best time to book a flight from Chicago to Prince Edward Island

Have a flexible travel schedule? Discover the best time to fly to Prince Edward Island from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Prince Edward Island
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Prince Edward Island

Get insights into the airlines that provide service to Prince Edward Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Prince Edward Island. Reviews last updated December 4, 2025.
Peruse reviews from past customers who have flown with United Airlines and Air Canada from Chicago to Prince Edward Island to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,066 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,066 reviews
United Airlines
7.4
Good
9,066 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Air Canada
7.1
Good
10,500 reviews
United Airlines
7.4
Good
9,066 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Prince Edward Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Prince Edward Island?

    Departing from Chicago to Prince Edward Island will take you 5h 40m. Chicago and Prince Edward Island are separated by a distance of 1258 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago to Prince Edward Island?

    The most popular route from Chicago to Prince Edward Island is Chicago Midway - Moncton Intl. You may also consider Chicago O'Hare Intl - Charlottetown or Chicago Midway - Charlottetown.

  • Can I find deals for flights from Chicago to Prince Edward Island that include hotel bookings?

    Yes. In addition to deals on Chicago to Prince Edward Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Prince Edward Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Prince Edward Island.

  • Can I find deals for business class flights from Chicago to Prince Edward Island?

    Yes. Cheapflights offers flight deals from Chicago to Prince Edward Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Chicago to Prince Edward Island

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Top 2 airlines flying from Chicago to Prince Edward Island

Discover the top 2 airlines that operate flights from Chicago to Prince Edward Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$236Average$555FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$295Average$738FlexibilityNo cancel feeOn-time69%

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