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Charlottetown

$594+ Cheap flights from Chicago (CHI) 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$586
(Mytrip)
From Chicago (CHI) to Charlottetown
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Find 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 September 16, 2025.

This Air Canada deal was found by Cheapflights users on 9/16. 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 11/143:55 pmORD - YYG
1 stop6h 25mAir Canada
Sun 11/165:05 amYYG - ORD
1 stop6h 08mAir Canada
Deal found 9/16$594
This Mytrip deal was found by Cheapflights users on 9/16. 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 11/1410:18 amORD - YYG
3 stops24h 44mMultiple Airlines
Sun 11/161:45 pmYYG - ORD
3 stops33h 15mMultiple Airlines
Deal found 9/16$607
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/148:50 amORD - YYG
2 stops13h 30mUnited Airlines
Sun 11/165:05 amYYG - ORD
1 stop6h 08mUnited Airlines
Deal found 9/16$679
This Porter Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 11/1411:00 amMDW - YYG
2 stops24h 02mPorter Airlines
Sun 11/161:45 pmYYG - MDW
2 stops22h 20mPorter Airlines
Deal found 9/16$778
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Mon 9/299:20 amMDW - YYG
3 stops25h 25mMultiple Airlines
Thu 10/26:40 amYYG - MDW
2 stops11h 44mMultiple Airlines
Deal found 9/16$881
This Mytrip deal was found by Cheapflights users on 9/16. 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 11/141:47 pmMDW - YYG
3 stops21h 15mMultiple Airlines
Sun 11/161:45 pmYYG - MDW
3 stops30h 33mMultiple Airlines
Deal found 9/16$949
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/189:35 amMDW - YYG
2 stops10h 14mMultiple Airlines
Sat 9/201:25 pmYYG - MDW
2 stops21h 53mMultiple Airlines
Deal found 9/14$1,024
This Mytrip deal was found by Cheapflights users on 9/14. 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 9/187:12 pmORD - YYG
3 stops24h 37mMultiple Airlines
Sat 9/206:40 amYYG - ORD
3 stops28h 33mMultiple Airlines
Deal found 9/14$1,134
This Air Canada deal was found by Cheapflights users on 9/14. 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 9/187:11 amORD - YYG
1 stop6h 21mAir Canada
Sun 9/215:20 amYYG - ORD
1 stop7h 33mAir Canada
Deal found 9/14$1,214
This Air Canada deal was found by Cheapflights users on 9/14. 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 9/188:40 amORD - YYG
1 stop4h 52mAir Canada
Sat 9/2011:25 amYYG - ORD
1 stop5h 30mAir Canada
Deal found 9/14$1,357

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 September 16, 2025.
Use the filters below to find and compare flights from Chicago to Charlottetown that are best for you.

Fly from

Chicago

Fly to

Charlottetown

Route

Depart

Return

Price

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 11/14

3:55 pm-12:20 am

1 stop6h 25m

Charlottetown

Sun 11/16

5:05 am-9:13 am

1 stop6h 08m

$594

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 11/14

10:18 am-1:02 pm

3 stops24h 44m

Charlottetown

Sun 11/16

1:45 pm-9:00 pm

3 stops33h 15m

$607

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 11/14

8:50 am-12:20 am

2 stops13h 30m

Charlottetown

Sun 11/16

5:05 am-9:13 am

1 stop6h 08m

$679

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Mon 9/29

9:20 am-12:45 pm

3 stops25h 25m

Charlottetown

Thu 10/2

6:40 am-4:24 pm

2 stops11h 44m

$881

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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

What is the cheapest time of day to fly from CHI to YYG?

Find hourly flight availability from Chicago to Charlottetown. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chicago to Charlottetown, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 17% versus a flight in the morning.

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 September 16, 2025.
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
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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 United Airlines can get you from Chicago to Charlottetown in just under 6h 25m. Your travel time can differ by up to 7h 05m. 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 $295.

  • 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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Alternative routes for Chicago to Charlottetown

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Charlottetown flights

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$236Average$555FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$295Average$738FlexibilityNo cancel feeOn-time69%

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