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Charlottetown

$347+ Cheap flights from Chicago (CHI) to Charlottetown (YYG)

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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
1 adult, Economy
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Find cheap flights from Chicago to Charlottetown with Cheapflights

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Cheap flight deals from Chicago to Charlottetown

Cheapest flights from Chicago to Charlottetown
Explore the most affordable flight options available from Chicago to Charlottetown. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/7. 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 5/273:20 pm
MDW
-
YYG
2 stops23h 15m
Multiple Airlines
Sun 5/3111:40 am
YYG
-
MDW
1 stop23h 55m
Multiple Airlines
Deal found 5/7$601
This Air Canada deal was found by Cheapflights users on 5/6. 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 9/168:45 am
ORD
-
YYG
1 stop4h 55m
Air Canada
Tue 9/224:30 pm
YYG
-
ORD
1 stop5h 42m
Air Canada
Deal found 5/6$649
This Air Canada deal was found by Cheapflights users on 5/3. 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 9/168:45 am
ORD
-
YYG
1 stop4h 55m
Air Canada
Sun 9/2011:20 am
YYG
-
ORD
2 stops10h 56m
Air Canada
Deal found 5/3$654
This Air Canada deal was found by Cheapflights users on 5/6. 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 8/168:45 am
ORD
-
YYG
1 stop4h 55m
Air Canada
Sat 8/224:30 pm
YYG
-
ORD
1 stop5h 35m
Air Canada
Deal found 5/6$679
This Air Canada deal was found by Cheapflights users on 5/5. 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 8/208:45 am
ORD
-
YYG
1 stop4h 55m
Air Canada
Sun 8/235:20 am
YYG
-
ORD
1 stop5h 40m
Air Canada
Deal found 5/5$684
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/2010:30 am
MDW
-
YYG
2 stops28h 05m
Multiple Airlines
Sun 5/2411:40 am
YYG
-
MDW
1 stop24h 05m
Multiple Airlines
Deal found 5/3$684
This Air Canada deal was found by Cheapflights users on 5/7. 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 5/273:50 pm
ORD
-
YYG
1 stop6h 12m
Air Canada
Sun 5/315:15 am
YYG
-
ORD
1 stop5h 45m
Air Canada
Deal found 5/7$689
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sun 9/2711:45 am
ORD
-
YYG
1 stop21h 10m
Multiple Airlines
Thu 10/15:20 pm
YYG
-
ORD
2 stops19h 40m
Multiple Airlines
Deal found 5/5$695
This Air Canada deal was found by Cheapflights users on 5/5. 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 6/198:40 pm
ORD
-
YYG
1 stop12h 55m
Air Canada
Fri 6/2611:20 am
YYG
-
ORD
1 stop5h 24m
Air Canada
Deal found 5/5$709
This oojo deal was found by Cheapflights users on 5/3. 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.
Wed 9/167:00 am
ORD
-
YYG
2 stops7h 35m
Porter Airlines
Tue 9/225:20 pm
YYG
-
ORD
2 stops19h 40m
Porter Airlines
Deal found 5/3$726
This oojo deal was found by Cheapflights users on 5/7. 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.
Wed 5/2710:30 am
MDW
-
YYG
2 stops28h 05m
Porter Airlines
Sun 5/315:20 pm
YYG
-
MDW
2 stops18h 15m
Porter Airlines
Deal found 5/7$750
This oojo deal was found by Cheapflights users on 5/5. 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 6/193:20 pm
MDW
-
YYG
2 stops23h 15m
Porter Airlines
Fri 6/2611:50 am
YYG
-
MDW
2 stops23h 50m
Porter Airlines
Deal found 5/5$770

Find flight deals from Chicago to Charlottetown

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Charlottetown (YYG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$601
(Kiwi.com)

One-way from

$347
(Air Canada)
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 Charlottetown
Search Deals
One-way flight from Chicago (CHI) to Charlottetown
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 May 8, 2026.
Use the filters below to find and compare flights from Chicago to Charlottetown that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 5/27

3:20 pm-4:35 pm

2 stops23h 15m

Charlottetown

Sun 5/31

11:40 am-9:35 am

1 stop23h 55m

$601

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 9/16

8:45 am-3:40 pm

1 stop4h 55m

Charlottetown

Sun 9/20

4:30 pm-8:12 pm

1 stop5h 42m

$649
Quickest round-trip

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 9/16

8:45 am-3:40 pm

1 stop4h 55m

Charlottetown

Tue 9/22

11:20 am-2:52 pm

1 stop5h 32m

$649

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Mon 9/21

8:45 am-3:40 pm

1 stop4h 55m

Charlottetown

Thu 9/24

4:30 pm-8:12 pm

1 stop5h 42m

$649

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Mon 8/3

8:45 am-3:40 pm

1 stop4h 55m

Charlottetown

Mon 8/10

4:30 pm-8:05 pm

1 stop5h 35m

$679

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 8/16

8:45 am-3:40 pm

1 stop4h 55m

Charlottetown

Sat 8/22

11:20 am-8:16 pm

2 stops10h 56m

$685

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 8/7

2:15 pm-11:59 pm

1 stop7h 44m

Charlottetown

Tue 8/11

12:30 pm-4:57 pm

1 stop6h 27m

$689

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 9/16

7:00 am-4:35 pm

2 stops7h 35m

Charlottetown

Tue 9/22

5:20 pm-11:00 am

2 stops19h 40m

$726

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Fri 6/19

3:20 pm-4:35 pm

2 stops23h 15m

Charlottetown

Fri 6/26

11:50 am-9:40 am

2 stops23h 50m

$770

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 5/20

3:20 pm-4:35 pm

2 stops23h 15m

Charlottetown

Sun 5/24

5:20 pm-2:35 pm

2 stops23h 15m

$861

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Chicago to Charlottetown

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Charlottetown in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Charlottetown flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Charlottetown flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Charlottetown flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Charlottetown flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Charlottetown flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Charlottetown

Have a flexible travel schedule? Discover the best time to fly to Charlottetown 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 Charlottetown
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Charlottetown

Get insights into the airlines that provide service to Charlottetown. 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 Charlottetown. Reviews last updated May 8, 2026.
Get a feel of what it's like to fly with United Airlines and Air Canada from Chicago to Charlottetown by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,694 reviews

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,694 reviews
United Airlines
7.4
Good
9,694 reviews

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Air Canada
7.1
Good
11,002 reviews
United Airlines
7.4
Good
9,694 reviews

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Located just 3.3 mi from the city center, Charlottetown is the airport most travelers will use when flying to Charlottetown from Chicago. Booking flights from Chicago to Charlottetown (YYG) should be relatively easy as there are 0 daily inbound flights from Chicago from 2 different airlines.

  • How long is the flight from Chicago to Charlottetown?

    Air Canada and Porter Airlines can get you from Chicago to Charlottetown in just under 4h 55m. Your travel time can differ by up to 18h 20m. The distance from Chicago to Charlottetown is about 1258 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Charlottetown round-trip?

    Currently priced at $236, Air Canada will fly you from Chicago to Charlottetown and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $241.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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.

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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Complete your trip

Complete your trip to Charlottetown by adding a car rental and/or hotel reservation to your travel itinerary.
Charlottetown car rentals
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Moncton Intl Airport car rentals

Top 2 airlines flying from Chicago to Charlottetown

Discover the top 2 airlines that operate flights from Chicago 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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$236Average$653FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$241Average$782FlexibilityNo cancel feeOn-time69%

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