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Prince Edward Island

$327+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$710
(FlightHub)

One-way from

$327
(Porter Airlines)
Provider with most accurate pricing for Chicago (CHI)-Charlottetown flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Charlottetown flights.
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From Chicago (CHI) to Prince Edward Island
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One-way flight from Chicago (CHI) 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 October 14, 2025.

This Air Canada deal was found by Cheapflights users on 10/14. 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 11/138:00 amORD - YYG
1 stop7h 40mAir Canada
Thu 11/205:05 amYYG - ORD
1 stop6h 08mAir Canada
Deal found 10/14$615
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Fri 11/283:55 pmORD - YYG
1 stop6h 25mUnited Airlines
Fri 12/511:15 amYYG - ORD
2 stops12h 23mUnited Airlines
Deal found 10/14$699
This United Airlines deal was found by Cheapflights users on 10/14. 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 11/136:02 amORD - YYG
2 stops9h 38mUnited Airlines
Thu 11/205:05 amYYG - ORD
1 stop6h 08mUnited Airlines
Deal found 10/14$700
This FlightHub deal was found by Cheapflights users on 10/14. 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.
Thu 11/134:15 pmMDW - YYG
2 stops18h 47mPorter Airlines
Thu 11/201:45 pmYYG - MDW
2 stops22h 20mPorter Airlines
Deal found 10/14$710
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/132:31 pmORD - YYG
3 stops20h 31mMultiple Airlines
Thu 11/201:45 pmYYG - ORD
2 stops25h 50mMultiple Airlines
Deal found 10/14$740
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/282:20 pmORD - YYG
3 stops20h 42mMultiple Airlines
Fri 12/51:45 pmYYG - ORD
3 stops26h 31mMultiple Airlines
Deal found 10/14$744
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2811:08 amORD - YYG
3 stops23h 54mMultiple Airlines
Fri 10/311:45 pmYYG - ORD
2 stops13h 18mMultiple Airlines
Deal found 10/14$769
This Air Canada deal was found by Cheapflights users on 10/13. 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 11/13:55 pmORD - YYG
1 stop6h 25mAir Canada
Tue 11/115:05 amYYG - ORD
1 stop9h 56mAir Canada
Deal found 10/13$773
This Air Canada deal was found by Cheapflights users on 10/14. 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 10/2810:00 amORD - YYG
1 stop5h 40mAir Canada
Fri 10/315:05 amYYG - ORD
1 stop6h 10mAir Canada
Deal found 10/14$826
This Porter Airlines deal was found by Cheapflights users on 10/13. 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.
Sat 11/112:45 pmMDW - YYG
2 stops23h 17mPorter Airlines
Tue 11/111:45 pmYYG - MDW
2 stops22h 20mPorter Airlines
Deal found 10/13$900
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/289:41 amMDW - YYG
3 stops25h 21mMultiple Airlines
Fri 12/51:45 pmYYG - MDW
3 stops30h 33mMultiple Airlines
Deal found 10/14$904
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:48 pmMDW - YYG
3 stops21h 14mMultiple Airlines
Fri 10/311:45 pmYYG - MDW
3 stops22h 45mMultiple Airlines
Deal found 10/14$958

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 October 14, 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 11/13

8:00 am-5:40 pm

1 stop7h 40m

Charlottetown

Thu 11/20

5:05 am-9:13 am

1 stop6h 08m

$615

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 11/28

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Fri 12/5

5:05 am-9:13 am

1 stop6h 08m

$615

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 11/28

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Fri 12/5

11:15 am-9:38 pm

2 stops12h 23m

$699

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 11/13

6:02 am-5:40 pm

2 stops9h 38m

Charlottetown

Thu 11/20

5:05 am-9:13 am

1 stop6h 08m

$700

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Thu 11/13

4:15 pm-1:02 pm

2 stops18h 47m

Charlottetown

Thu 11/20

1:45 pm-10:05 am

2 stops22h 20m

$710

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 11/13

2:31 pm-1:02 pm

3 stops20h 31m

Charlottetown

Thu 11/20

1:45 pm-1:35 pm

2 stops25h 50m

$740

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 11/28

2:20 pm-1:02 pm

3 stops20h 42m

Charlottetown

Fri 12/5

1:45 pm-2:16 pm

3 stops26h 31m

$744

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 10/28

11:08 am-1:02 pm

3 stops23h 54m

Charlottetown

Fri 10/31

1:45 pm-1:03 am

2 stops13h 18m

$769

ChicagoMoncton

MDW - YQM

MDWYQM

Chicago Midway

Tue 4/7

4:15 pm-1:00 pm

1 stop18h 45m

Moncton Intl

Wed 4/8

6:55 pm-10:05 am

1 stop17h 10m

$777

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 11/1

8:20 pm-6:40 pm

2 stops20h 20m

Charlottetown

Tue 11/11

5:05 am-3:10 pm

1 stop12h 05m

$858

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 21 results
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2
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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 October 14, 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
8,976 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,976 reviews
United Airlines
7.4
Good
8,976 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Air Canada
7.1
Good
10,297 reviews
United Airlines
7.4
Good
8,976 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 6h 25m. 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 - Charlottetown. You may also consider Chicago O'Hare Intl - 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$236Average$555FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$241Average$738FlexibilityNo cancel feeOn-time69%

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