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Cheap flights from Chicago to Prince Edward Island from C$ 806

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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap 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 11 September 2025.

Round-trip from

C$ 806
Porter Airlines
  • Porter Airlines
  • 3/10-6/10
  • 4 total stops
  • 21h 58m total
  • Chicago to Prince Edward Island
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Find 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 11 September 2025.

Fri 3/109:35 a.m.MDW - YYG
2 stops10h 14mPorter Airlines
Mon 6/106:40 a.m.YYG - MDW
2 stops11h 44mPorter Airlines
Deal found 10/9C$ 806
Sun 26/108:00 a.m.ORD - YYG
1 stop7h 40mAir Canada
Sun 2/115:05 a.m.YYG - ORD
1 stop6h 08mAir Canada
Deal found 11/9C$ 808
Tue 23/99:20 a.m.MDW - YYG
2 stops23h 50mMultiple Airlines
Fri 26/96:40 a.m.YYG - MDW
2 stops11h 44mMultiple Airlines
Deal found 9/9C$ 851
Fri 3/109:55 a.m.ORD - YYG
1 stop5h 38mAir Canada
Mon 6/105:20 a.m.YYG - ORD
1 stop5h 49mAir Canada
Deal found 10/9C$ 888
Sun 26/108:00 a.m.ORD - YYG
1 stop7h 40mUnited Airlines
Sun 2/116:30 p.m.YYG - ORD
2 stops22h 54mUnited Airlines
Deal found 11/9C$ 967
Sun 26/102:20 p.m.ORD - YYG
3 stops20h 42mMultiple Airlines
Sun 2/111:45 p.m.YYG - ORD
3 stops30h 53mMultiple Airlines
Deal found 11/9C$ 995
Sun 26/104:15 p.m.MDW - YYG
2 stops18h 47mPorter Airlines
Sun 2/111:45 p.m.YYG - MDW
2 stops27h 35mPorter Airlines
Deal found 11/9C$ 1,043
Wed 24/95:20 p.m.MDW - YYG
2 stops17h 25mMultiple Airlines
Sat 27/96:40 a.m.YYG - MDW
3 stops12h 55mMultiple Airlines
Deal found 11/9C$ 1,197
Sun 26/104:15 p.m.MDW - YYG
2 stops18h 47mMultiple Airlines
Sun 2/111:45 p.m.YYG - MDW
3 stops25h 23mMultiple Airlines
Deal found 11/9C$ 1,211
Thu 18/93:50 p.m.ORD - YYG
1 stop6h 08mAir Canada
Sun 21/95:20 a.m.YYG - ORD
1 stop7h 33mAir Canada
Deal found 11/9C$ 1,441
Wed 24/95:20 p.m.MDW - YYG
2 stops17h 25mPorter Airlines
Sat 27/96:40 a.m.YYG - MDW
2 stops35h 44mPorter Airlines
Deal found 11/9C$ 1,594

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 11 September 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

MDW - YYG

MDWYYG

Chicago Midway

Fri 3/10

9:35 a.m.-9:49 p.m.

2 stops10h 14m

Charlottetown

Mon 6/10

6:40 a.m.-4:24 p.m.

2 stops11h 44m

C$ 806

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 26/10

8:00 a.m.-5:40 p.m.

1 stop7h 40m

Charlottetown

Sun 2/11

5:05 a.m.-9:13 a.m.

1 stop6h 08m

C$ 808

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 23/9

9:20 a.m.-11:10 a.m.

2 stops23h 50m

Charlottetown

Fri 26/9

6:40 a.m.-4:24 p.m.

2 stops11h 44m

C$ 851

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 3/10

9:55 a.m.-5:33 p.m.

1 stop5h 38m

Charlottetown

Mon 6/10

5:20 a.m.-9:09 a.m.

1 stop5h 49m

C$ 888

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 26/10

8:00 a.m.-5:40 p.m.

1 stop7h 40m

Charlottetown

Sun 2/11

6:30 p.m.-3:24 p.m.

2 stops22h 54m

C$ 967

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-1:02 p.m.

3 stops20h 42m

Charlottetown

Sun 2/11

1:45 p.m.-6:38 p.m.

3 stops30h 53m

C$ 995

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Sun 26/10

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

2 stops18h 47m

Charlottetown

Sun 2/11

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

2 stops27h 35m

C$ 1,043

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 24/9

5:20 p.m.-12:45 p.m.

2 stops17h 25m

Charlottetown

Sat 27/9

6:40 a.m.-5:35 p.m.

3 stops12h 55m

C$ 1,197

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Sun 26/10

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

2 stops18h 47m

Charlottetown

Sun 2/11

1:45 p.m.-1:08 p.m.

3 stops25h 23m

C$ 1,211

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 24/9

5:20 p.m.-12:45 p.m.

2 stops17h 25m

Charlottetown

Sat 27/9

6:40 a.m.-4:24 p.m.

2 stops35h 44m

C$ 1,594

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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?

    Porter Airlines, Air Canada, and United Airlines can get you from Chicago to Prince Edward Island in just under 7h 40m. Your travel time can differ by up to 2h 34m. 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.

  • What is the cheapest month to book a flight from Chicago to Prince Edward Island?

    Currently, June is the cheapest month in which you can book a flight from Chicago to Prince Edward Island (average of C$ 205). Flying from Chicago to Prince Edward Island in December is currently the most expensive (average of C$ 481). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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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