HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Charlottetown

$609+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Charlottetown with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$609
(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

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 October 30, 2025.

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 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 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
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.
Fri 12/127:10 amORD - YYG
3 stops27h 52mMultiple Airlines
Fri 12/191:45 pmYYG - ORD
2 stops26h 24mMultiple Airlines
Deal found 10/28$965
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.
Fri 12/124:15 pmMDW - YYG
2 stops18h 47mMultiple Airlines
Fri 12/191:45 pmYYG - MDW
3 stops23h 21mMultiple Airlines
Deal found 10/28$1,288
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.
Sat 11/13:55 pmORD - YYG
1 stop6h 25mAir Canada
Sun 11/25:05 amYYG - ORD
1 stop6h 08mAir Canada
Deal found 10/27$1,402

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 October 30, 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

Mon 4/13

4:15 pm-12:22 am

1 stop6h 07m

Charlottetown

Sat 4/18

11:15 am-2:55 pm

1 stop5h 40m

$609

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

Mon 4/13

9:00 am-5:37 pm

1 stop6h 37m

Charlottetown

Sat 4/18

11:15 am-6:33 pm

2 stops9h 18m

$689

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

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

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

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Fri 12/12

9:05 pm-12:20 am

2 stops25h 15m

Charlottetown

Fri 12/19

11:15 am-9:39 pm

2 stops12h 24m

$893

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 12 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Charlottetown flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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

Currently, June is the cheapest month in which you can book a flight from Chicago to Charlottetown (average of $165). Flying from Chicago 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.

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 October 30, 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
8,998 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,381 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 6h 07m. Your travel time can differ by up to 17h 55m. 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.

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

    Currently, June is the cheapest month in which you can book a flight from Chicago to Charlottetown (average of $165). Flying from Chicago 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$236Average$555FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$295Average$738FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.