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Charlottetown

$644+ Cheap flights from Illinois to Charlottetown (YYG)

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YYG
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Illinois to Charlottetown

Keep the following information in mind while searching for Illinois to Charlottetown flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$644
(Air Canada)
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 Illinois to Charlottetown
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Find flight deals from Illinois to Charlottetown

Cheapest flights from Illinois to Charlottetown
Explore the most affordable flight options available from Illinois to Charlottetown. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Air Canada deal was found by Cheapflights users on 10/27. 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 12/113:55 pmORD - YYG
1 stop6h 25mAir Canada
Thu 12/185:05 amYYG - ORD
1 stop6h 08mAir Canada
Deal found 10/27$644
This FlightHub deal was found by Cheapflights users on 10/28. 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 11/2511:00 amMDW - YYG
2 stops24h 02mPorter Airlines
Tue 12/21:45 pmYYG - MDW
2 stops22h 20mPorter Airlines
Deal found 10/28$667
This Air Canada deal was found by Cheapflights users on 10/28. 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 11/253:55 pmORD - YYG
1 stop6h 25mAir Canada
Tue 12/26:30 pmYYG - ORD
1 stop16h 43mAir Canada
Deal found 10/28$668
This Mytrip deal was found by Cheapflights users on 10/28. 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 11/252:01 pmORD - YYG
3 stops21h 01mMultiple Airlines
Tue 12/21:45 pmYYG - ORD
2 stops21h 32mMultiple Airlines
Deal found 10/28$671
This Mytrip deal was found by Cheapflights users on 10/28. 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 11/259:41 amMDW - YYG
3 stops25h 21mMultiple Airlines
Tue 12/21:45 pmYYG - MDW
2 stops22h 20mMultiple Airlines
Deal found 10/28$728
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/118:45 amORD - YYG
2 stops13h 35mUnited Airlines
Thu 12/185:05 amYYG - ORD
1 stop6h 08mUnited Airlines
Deal found 10/27$729
This oojo deal was found by Cheapflights users on 10/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:00 amMDW - YYG
2 stops24h 02mPorter Airlines
Fri 12/191:45 pmYYG - MDW
2 stops27h 35mPorter Airlines
Deal found 10/28$745
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 11/253:55 pmORD - YYG
1 stop6h 25mUnited Airlines
Tue 12/211:15 amYYG - ORD
2 stops14h 28mUnited Airlines
Deal found 10/28$757
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Sat 12/279:41 amORD - YYG
3 stops25h 21mMultiple Airlines
Mon 12/291:45 pmYYG - ORD
3 stops20h 46mMultiple Airlines
Deal found 10/26$856
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/269:15 pmORD - YYG
2 stops25h 05mUnited Airlines
Sun 12/286:30 pmYYG - ORD
2 stops27h 55mUnited Airlines
Deal found 10/27$858
This Air Canada deal was found by Cheapflights users on 10/28. 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.
Fri 12/122:00 pmORD - YYG
1 stop8h 20mAir Canada
Fri 12/195:05 amYYG - ORD
1 stop9h 56mAir Canada
Deal found 10/28$873
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/129:05 pmORD - YYG
2 stops25h 15mUnited Airlines
Fri 12/1911:15 amYYG - ORD
2 stops12h 24mUnited Airlines
Deal found 10/28$893

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Charlottetown 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 29, 2025.
Use the filters below to find and compare flights from Illinois to Charlottetown that are best for you.

Fly from

Illinois

Fly to

Charlottetown

Route

Depart

Return

Price

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 11/25

11:00 am-1:02 pm

2 stops24h 02m

Charlottetown

Tue 12/2

1:45 pm-10:05 am

2 stops22h 20m

$667

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 11/25

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Tue 12/2

6:30 pm-9:13 am

1 stop16h 43m

$668

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 11/25

2:01 pm-1:02 pm

3 stops21h 01m

Charlottetown

Tue 12/2

1:45 pm-2:48 pm

3 stops27h 03m

$698

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 11/25

9:41 am-1:02 pm

3 stops25h 21m

Charlottetown

Tue 12/2

1:45 pm-10:05 am

2 stops22h 20m

$728

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Thu 12/11

8:45 am-12:20 am

2 stops13h 35m

Charlottetown

Thu 12/18

5:05 am-9:13 am

1 stop6h 08m

$729

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Fri 12/12

11:00 am-1:02 pm

2 stops24h 02m

Charlottetown

Fri 12/19

1:45 pm-3:20 pm

2 stops27h 35m

$745

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 11/25

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Tue 12/2

11:15 am-11:43 pm

2 stops14h 28m

$757

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 12/27

9:41 am-1:02 pm

3 stops25h 21m

Charlottetown

Mon 12/29

1:45 pm-8:31 am

3 stops20h 46m

$856

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 12/26

9:15 pm-12:20 am

2 stops25h 05m

Charlottetown

Sun 12/28

6:30 pm-8:25 pm

2 stops27h 55m

$858

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 12/12

2:00 pm-12:20 am

1 stop8h 20m

Charlottetown

Fri 12/19

5:05 am-1:01 pm

1 stop9h 56m

$873

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 17 results
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Best time to book a flight from Illinois to Charlottetown

Have a flexible travel schedule? Discover the best time to fly to Charlottetown from Illinois 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 Illinois to Charlottetown

What is the cheapest month to book a flight from Illinois to Charlottetown?

Currently, June is the cheapest month in which you can book a flight from Illinois to Charlottetown (average of $165). Flying from Illinois to Charlottetown in December is currently the most expensive (average of $333). 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.

Related info for your journey

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

  • What airport do you fly into for flights to Charlottetown from Illinois?

    Most people fly into Charlottetown (YYG) if they book a flight to Charlottetown from Illinois. Charlottetown is conveniently located just 3.3 mi from Charlottetown’s city center.

  • How long is the flight from Illinois to Charlottetown?

    For as low as $668, Porter Airlines can have you in Charlottetown from Illinois in 6h 25m. The distance between Illinois and Charlottetown is about 1258 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Illinois to Charlottetown that include hotel bookings?

    Yes. In addition to deals on Illinois to Charlottetown flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Charlottetown?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Charlottetown.

  • Can I find deals for business class flights from Illinois to Charlottetown?

    Yes. Cheapflights offers flight deals from Illinois to Charlottetown 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 Illinois to Charlottetown?

    Currently, June is the cheapest month in which you can book a flight from Illinois to Charlottetown (average of $165). Flying from Illinois to Charlottetown in December is currently the most expensive (average of $333). 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

Traveling to a place near Charlottetown?

Book flights to Charlottetown if you plan to visit one of these locations
Summerside

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Alternative routes for Illinois to Charlottetown

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Illinois to Charlottetown

Discover the top 2 airlines that operate flights from Illinois to Charlottetown. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$236Average$555FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$295Average$738FlexibilityNo cancel feeOn-time69%

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