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Prince Edward Island

$292+ Cheap flights from Chicago (CHI) to Prince Edward Island

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
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 January 20, 2026.

This Air Canada deal was found by Cheapflights users on 1/17. 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.
Thu 4/97:55 am
ORD
-
YYG
1 stop7h 42m
Air Canada
Sun 4/1211:15 am
YYG
-
ORD
1 stop5h 40m
Air Canada
Deal found 1/17$574
This FlightHub deal was found by Cheapflights users on 1/19. 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.
Fri 4/1711:00 am
MDW
-
YQM
2 stops10h 30m
Porter Airlines
Sat 4/256:40 am
YQM
-
MDW
2 stops7h 10m
Porter Airlines
Deal found 1/19$577
This Air Canada deal was found by Cheapflights users on 1/18. 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.
Thu 3/58:00 am
ORD
-
YYG
1 stop7h 40m
Air Canada
Thu 3/125:05 am
YYG
-
ORD
1 stop6h 08m
Air Canada
Deal found 1/18$578
This Air Canada deal was found by Cheapflights users on 1/18. 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 2/186:00 pm
ORD
-
YYG
1 stop14h 33m
Multiple Airlines
Fri 2/2011:15 am
YYG
-
ORD
1 stop5h 40m
Multiple Airlines
Deal found 1/18$622
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
-
YQM
2 stops21h 43m
Multiple Airlines
Wed 3/116:55 pm
YQM
-
MDW
1 stop17h 10m
Multiple Airlines
Deal found 1/18$627
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:00 am
MDW
-
YQM
1 stop24h 00m
Porter Airlines
Wed 3/116:55 pm
YQM
-
MDW
1 stop17h 10m
Porter Airlines
Deal found 1/18$643
This Air Canada deal was found by Cheapflights users on 1/18. 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 6/108:45 am
ORD
-
YYG
1 stop4h 52m
Air Canada
Mon 6/154:20 pm
YYG
-
ORD
1 stop5h 48m
Air Canada
Deal found 1/18$653
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:20 pm
MDW
-
YYG
1 stop15h 35m
Multiple Airlines
Mon 9/2111:40 am
YYG
-
MDW
1 stop23h 05m
Multiple Airlines
Deal found 1/19$653
This United Airlines deal was found by Cheapflights users on 1/18. 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.
Thu 3/58:45 am
ORD
-
YYG
2 stops13h 35m
United Airlines
Thu 3/125:05 am
YYG
-
ORD
1 stop6h 08m
United Airlines
Deal found 1/18$663
This Air Canada deal was found by Cheapflights users on 1/19. 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.
Sun 6/148:45 am
ORD
-
YYG
1 stop4h 52m
Air Canada
Fri 6/1911:20 am
YYG
-
ORD
2 stops10h 27m
Air Canada
Deal found 1/19$666
This Porter Airlines deal was found by Cheapflights users on 1/19. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:40 am
MDW
-
YYG
2 stops11h 40m
Porter Airlines
Mon 9/216:40 am
YYG
-
MDW
2 stops11h 44m
Porter Airlines
Deal found 1/19$667
This Air Canada deal was found by Cheapflights users on 1/19. 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 2/186:00 pm
ORD
-
YYG
1 stop14h 33m
Multiple Airlines
Tue 2/245:05 am
YYG
-
ORD
1 stop6h 08m
Multiple Airlines
Deal found 1/19$669

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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$574
(Air Canada)

One-way from

$292
(Trip.com)
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
One-way flight 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 January 20, 2026.
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 4/9

7:55 am-5:37 pm

1 stop7h 42m

Charlottetown

Sun 4/12

11:15 am-2:55 pm

1 stop5h 40m

$574

ChicagoMoncton

MDW - YQM

MDWYQM

Chicago Midway

Fri 4/17

11:00 am-11:30 pm

2 stops10h 30m

Moncton Intl

Sat 4/25

6:40 am-11:50 am

2 stops7h 10m

$577

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 3/5

8:00 am-5:40 pm

1 stop7h 40m

Charlottetown

Thu 3/12

5:05 am-9:13 am

1 stop6h 08m

$578

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 2/18

3:55 pm-10:33 am

2 stops16h 38m

Charlottetown

Fri 2/20

11:15 am-2:55 pm

1 stop5h 40m

$612

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 2/18

6:00 pm-10:33 am

1 stop14h 33m

Charlottetown

Fri 2/20

11:15 am-2:55 pm

1 stop5h 40m

$622

ChicagoMoncton

MDW - YQM

MDWYQM

Chicago Midway

Wed 3/4

7:15 am-6:58 am

2 stops21h 43m

Moncton Intl

Wed 3/11

6:55 pm-10:05 am

1 stop17h 10m

$627

ChicagoMoncton

MDW - YQM

MDWYQM

Chicago Midway

Wed 3/4

11:00 am-1:00 pm

1 stop24h 00m

Moncton Intl

Wed 3/11

6:55 pm-10:05 am

1 stop17h 10m

$643

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Mon 6/15

8:45 am-3:30 pm

1 stop4h 45m

Charlottetown

Sat 6/20

4:20 pm-8:05 pm

1 stop5h 45m

$653

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 6/16

8:45 am-3:37 pm

1 stop4h 52m

Charlottetown

Sun 6/21

4:20 pm-8:05 pm

1 stop5h 45m

$653

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 6/10

8:45 am-3:37 pm

1 stop4h 52m

Charlottetown

Mon 6/15

4:20 pm-8:08 pm

1 stop5h 48m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 29 results
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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 January 20, 2026.
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
9,183 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,183 reviews
United Airlines
7.4
Good
9,183 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Air Canada
7.1
Good
10,637 reviews
United Airlines
7.4
Good
9,183 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 7h 42m. 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 O'Hare Intl - Charlottetown. You may also consider Chicago Midway - Charlottetown or Chicago Midway - Moncton Intl.

  • 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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$555FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$241Average$738FlexibilityNo cancel feeOn-time69%

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