$279 Cheap Flights from Chicago (ORD) to Charlottetown (YYG)

View $279 flight on Mon, Sep 14, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Charlottetown, PE (YYG)

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Cheap Flights from Chicago to Charlottetown (ORD-YYG)

Prices were available within the past 7 days and start at $279 for one-way flights and $566 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Sep 9 - Wed, Sep 16
ORD
Chicago
YYG
Charlottetown
$566 Roundtrip, found 4 days ago
$566
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Sep 9 from Chicago to Charlottetown, returning Wed, Sep 16, priced at $566 found 4 days ago
Air Canada
Tue, May 12 - Tue, May 19
ORD
Chicago
YYG
Charlottetown
$570 Roundtrip, found 5 days ago
$570
Roundtrip
found 5 days ago
Select Air Canada flight, departing Tue, May 12 from Chicago to Charlottetown, returning Tue, May 19, priced at $570 found 5 days ago
Air Canada
Wed, Jul 1 - Sat, Jul 4
ORD
Chicago
YYG
Charlottetown
$572 Roundtrip, found 6 days ago
$572
Roundtrip
found 6 days ago
Select Air Canada flight, departing Wed, Jul 1 from Chicago to Charlottetown, returning Sat, Jul 4, priced at $572 found 6 days ago
United
Mon, Sep 14 - Sat, Sep 19
ORD
Chicago
YYG
Charlottetown
$575 Roundtrip, found 2 days ago
$575
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep 14 from Chicago to Charlottetown, returning Sat, Sep 19, priced at $575 found 2 days ago
Air Canada
Thu, Mar 12 - Sat, Mar 21
ORD
Chicago
YYG
Charlottetown
$577 Roundtrip, found 20 hours ago
$577
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Thu, Mar 12 from Chicago to Charlottetown, returning Sat, Mar 21, priced at $577 found 20 hours ago
United
Mon, Sep 14 - Sat, Sep 19
ORD
Chicago
YYG
Charlottetown
$582 Roundtrip, found 2 days ago
$582
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep 14 from Chicago to Charlottetown, returning Sat, Sep 19, priced at $582 found 2 days ago
United
Mon, Sep 14 - Sat, Sep 19
ORD
Chicago
YYG
Charlottetown
$585 Roundtrip, found 2 days ago
$585
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep 14 from Chicago to Charlottetown, returning Sat, Sep 19, priced at $585 found 2 days ago
United
Thu, Mar 12 - Sat, Mar 21
ORD
Chicago
YYG
Charlottetown
$586 Roundtrip, found 20 hours ago
$586
Roundtrip
found 20 hours ago
Select United flight, departing Thu, Mar 12 from Chicago to Charlottetown, returning Sat, Mar 21, priced at $586 found 20 hours ago
Air Canada
Mon, Sep 14 - Sat, Sep 19
ORD
Chicago
YYG
Charlottetown
$596 Roundtrip, found 2 days ago
$596
Roundtrip
found 2 days ago
Select Air Canada flight, departing Mon, Sep 14 from Chicago to Charlottetown, returning Sat, Sep 19, priced at $596 found 2 days ago
United
Thu, Mar 12 - Sat, Mar 21
ORD
Chicago
YYG
Charlottetown
$596 Roundtrip, found 20 hours ago
$596
Roundtrip
found 20 hours ago
Select United flight, departing Thu, Mar 12 from Chicago to Charlottetown, returning Sat, Mar 21, priced at $596 found 20 hours ago

Alternative airports near Charlottetown

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Charlottetown, PE YYG. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $733
YYG
Charlottetown, PE
CheapestClosest
Average driving time to city center7 min
Flights from $733

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG) cost?
Lock in a cheap one-way flight from $279 or cheap return flight from $566 from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG)?
The cheapest month to fly from ORD to YYG is September, when there's less demand. Off-peak season is often when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG)?
To find the cheapest airline that'll fly you from ORD to YYG, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG)?
There aren't any daily direct flights available from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG). But you can book flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from ORD to YYG?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG)?
To reach Charlottetown Airport (YYG) on time, select a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG) last-minute?
Holding off until right before your break to book a ticket from ORD to YYG often results in higher prices. While you may come across some last-minute deals, they're not always guaranteed. Be flexible with your itinerary to maximize your chances of scoring a bargain.
Is it cheaper to book an ORD to YYG flight and hotel package?
Securing an ORD to YYG flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our impressive range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Charlottetown Airport (YYG)?
If you reserved your ORD to YYG flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Charlottetown
Airlines serving
Air Canada, United
Roundtrip price
$565
Distance
1258 mi

Book with confidence

Chicago to Charlottetown Flights

The cheapest times to fly from Chicago to Charlottetown

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Charlottetown are during the month of September. You can find some of the cheapest flights from Chicago to Charlottetown with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Charlottetown

Sunday is one of the best days to book for cheap flights from Chicago to Charlottetown: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Charlottetown

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Charlottetown in 2025. You can also book with separate airlines for your outbound and return journeys, from $279 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Charlottetown flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Charlottetown airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Charlottetown Flights

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*Available to One Key members.