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Cheap flights from Chicago to Prince Edward Island from C$ 839

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
28 Feb — 7 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Prince Edward Island

Enter your travel dates to find the best prices.

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 29 January 2026.

Thu 9/49:50 a.m.
ORD
-
YYG
1 stop5h 47m
Air Canada
Sun 12/45:15 a.m.
YYG
-
ORD
1 stop5h 55m
Air Canada
Deal found 26/1C$ 839
Fri 29/55:35 p.m.
MDW
-
YYG
2 stops21h 00m
Multiple Airlines
Wed 3/611:40 a.m.
YYG
-
MDW
1 stop24h 00m
Multiple Airlines
Deal found 28/1C$ 847
Wed 10/62:15 p.m.
ORD
-
YYG
1 stop7h 47m
Air Canada
Mon 15/612:30 p.m.
YYG
-
ORD
1 stop6h 29m
Air Canada
Deal found 27/1C$ 870
Fri 29/58:45 a.m.
ORD
-
YYG
1 stop4h 52m
Air Canada
Wed 3/64:20 p.m.
YYG
-
ORD
1 stop21h 00m
Air Canada
Deal found 29/1C$ 872
Fri 29/58:45 a.m.
ORD
-
YYG
1 stop4h 52m
Multiple Airlines
Wed 3/65:15 a.m.
YYG
-
ORD
1 stop6h 33m
Multiple Airlines
Deal found 27/1C$ 885
Mon 13/78:45 a.m.
ORD
-
YYG
1 stop4h 45m
Air Canada
Thu 16/74:20 p.m.
YYG
-
ORD
1 stop5h 45m
Air Canada
Deal found 27/1C$ 901
Thu 18/63:45 p.m.
ORD
-
YYG
1 stop6h 14m
Air Canada
Thu 2/74:20 p.m.
YYG
-
ORD
1 stop5h 45m
Air Canada
Deal found 28/1C$ 908
Wed 16/910:00 a.m.
ORD
-
YYG
1 stop5h 34m
Air Canada
Sun 20/95:25 a.m.
YYG
-
ORD
1 stop7h 28m
Air Canada
Deal found 26/1C$ 914
Thu 26/211:05 a.m.
MDW
-
YYG
2 stops24h 00m
Porter Airlines
Thu 5/31:45 p.m.
YYG
-
MDW
2 stops22h 20m
Porter Airlines
Deal found 28/1C$ 939
Wed 8/44:15 p.m.
MDW
-
YYG
2 stops18h 47m
Porter Airlines
Sun 12/41:45 p.m.
YYG
-
MDW
2 stops22h 20m
Porter Airlines
Deal found 28/1C$ 973
Thu 12/211:05 a.m.
MDW
-
YYG
2 stops24h 00m
Porter Airlines
Tue 17/21:45 p.m.
YYG
-
MDW
2 stops22h 25m
Porter Airlines
Deal found 27/1C$ 1,028
Fri 29/55:35 p.m.
MDW
-
YYG
3 stops21h 00m
Porter Airlines
Wed 3/65:20 p.m.
YYG
-
MDW
2 stops18h 20m
Porter Airlines
Deal found 28/1C$ 1,100

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 29 January 2026.

Round-trip from

C$ 839
Air Canada
  • Air Canada
  • 9/4-12/4
  • 2 total stops
  • 11h 42m total
  • Chicago 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 629,999 searches. Data last updated 29 January 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 9/4

9:50 a.m.-5:37 p.m.

1 stop5h 47m

Charlottetown

Sun 12/4

5:15 a.m.-9:10 a.m.

1 stop5h 55m

C$ 839

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Fri 29/5

5:35 p.m.-4:35 p.m.

2 stops21h 00m

Charlottetown

Wed 3/6

11:40 a.m.-9:40 a.m.

1 stop24h 00m

C$ 847

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 10/6

3:45 p.m.-12:02 a.m.

1 stop6h 17m

Charlottetown

Mon 15/6

11:20 a.m.-8:16 p.m.

2 stops10h 56m

C$ 870

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 29/5

8:45 a.m.-3:37 p.m.

1 stop4h 52m

Charlottetown

Wed 3/6

4:20 p.m.-11:20 a.m.

1 stop21h 00m

C$ 872

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 29/5

8:45 a.m.-3:37 p.m.

1 stop4h 52m

Charlottetown

Wed 3/6

5:15 a.m.-9:48 a.m.

1 stop6h 33m

C$ 885

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Mon 13/7

8:45 a.m.-3:30 p.m.

1 stop4h 45m

Charlottetown

Thu 16/7

4:20 p.m.-8:05 p.m.

1 stop5h 45m

C$ 901

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 15/7

8:45 a.m.-3:30 p.m.

1 stop4h 45m

Charlottetown

Sat 18/7

4:20 p.m.-8:05 p.m.

1 stop5h 45m

C$ 901

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Thu 26/2

11:05 a.m.-1:05 p.m.

2 stops24h 00m

Charlottetown

Thu 5/3

1:45 p.m.-10:05 a.m.

2 stops22h 20m

C$ 939

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 8/4

4:15 p.m.-1:02 p.m.

2 stops18h 47m

Charlottetown

Sun 12/4

1:45 p.m.-3:20 p.m.

2 stops27h 35m

C$ 973

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Thu 12/2

11:05 a.m.-1:05 p.m.

2 stops24h 00m

Charlottetown

Tue 17/2

1:45 p.m.-10:10 a.m.

2 stops22h 25m

C$ 1,028

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 13 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.

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?

    Air Canada and Porter Airlines can get you from Chicago to Prince Edward Island in just under 5h 47m. Your travel time can differ by up to 18h 13m. Chicago and Prince Edward Island are separated by a distance of 2025 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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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How does Cheapflights help users find flights from Chicago to Prince Edward Island?

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Can Cheapflights find flights from Chicago to Prince Edward Island with no change fees?

Need flexible booking options for your flight to Prince Edward Island from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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