$196 Cheap Flights from Charlottetown (YYG) to Chicago (ORD)

View $196 flight on Sat, Dec 6, 2025Opens in a new window

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

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Cheap Flights from Charlottetown to Chicago (YYG-ORD)

Prices were available within the past 7 days and start at $196 for one-way flights and $471 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Jul 23 - Tue, Jul 28
YYG
Charlottetown
ORD
Chicago
$471 Roundtrip, found 5 days ago
$471
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Jul 23 from Charlottetown to Chicago, returning Tue, Jul 28, priced at $471 found 5 days ago
Air Canada
Thu, Jan 15 - Tue, Feb 3
YYG
Charlottetown
ORD
Chicago
$478 Roundtrip, found 4 days ago
$478
Roundtrip
found 4 days ago
Select Air Canada flight, departing Thu, Jan 15 from Charlottetown to Chicago, returning Tue, Feb 3, priced at $478 found 4 days ago
Air Canada
Thu, Jul 23 - Tue, Jul 28
YYG
Charlottetown
ORD
Chicago
$484 Roundtrip, found 5 days ago
$484
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Jul 23 from Charlottetown to Chicago, returning Tue, Jul 28, priced at $484 found 5 days ago
Air Canada
Mon, Feb 9 - Tue, Feb 24
YYG
Charlottetown
ORD
Chicago
$489 Roundtrip, found 4 days ago
$489
Roundtrip
found 4 days ago
Select Air Canada flight, departing Mon, Feb 9 from Charlottetown to Chicago, returning Tue, Feb 24, priced at $489 found 4 days ago
Air Canada
Thu, Aug 20 - Thu, Aug 27
YYG
Charlottetown
ORD
Chicago
$499 Roundtrip, found 5 days ago
$499
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Aug 20 from Charlottetown to Chicago, returning Thu, Aug 27, priced at $499 found 5 days ago
Air Canada
Sat, Feb 21 - Fri, Mar 6
YYG
Charlottetown
ORD
Chicago
$501 Roundtrip, found 4 days ago
$501
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Feb 21 from Charlottetown to Chicago, returning Fri, Mar 6, priced at $501 found 4 days ago
Air Canada
Thu, Aug 20 - Thu, Aug 27
YYG
Charlottetown
ORD
Chicago
$504 Roundtrip, found 5 days ago
$504
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Aug 20 from Charlottetown to Chicago, returning Thu, Aug 27, priced at $504 found 5 days ago
Air Canada
Fri, Jan 16 - Sun, Feb 1
YYG
Charlottetown
ORD
Chicago
$505 Roundtrip, found 4 days ago
$505
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Jan 16 from Charlottetown to Chicago, returning Sun, Feb 1, priced at $505 found 4 days ago
Air Canada
Tue, Mar 3 - Tue, Mar 17
YYG
Charlottetown
ORD
Chicago
$507 Roundtrip, found 4 days ago
$507
Roundtrip
found 4 days ago
Select Air Canada flight, departing Tue, Mar 3 from Charlottetown to Chicago, returning Tue, Mar 17, priced at $507 found 4 days ago
United
Thu, Jul 23 - Tue, Jul 28
YYG
Charlottetown
ORD
Chicago
$527 Roundtrip, found 5 days ago
$527
Roundtrip
found 5 days ago
Select United flight, departing Thu, Jul 23 from Charlottetown to Chicago, returning Tue, Jul 28, priced at $527 found 5 days ago
Flights from Charlottetown (YYG) to Chicago (ORD)
Origin airport
Charlottetown
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, United
Roundtrip price
$471
Distance
1258 mi

Charlottetown to Chicago Flights

The cheapest times to fly from Charlottetown to Chicago

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 Charlottetown to Chicago are during the month of July. You can find some of the cheapest flights from Charlottetown to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Charlottetown to Chicago

Sunday is one of the best days to book for cheap flights from Charlottetown to Chicago: 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 Charlottetown to Chicago

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 Charlottetown to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $196 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 Charlottetown to Chicago 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 Charlottetown to Chicago 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.

 

Frequently asked questions

How much does a flight from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $196 or cheap return flight from $471 from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD)?
July is the most affordable month to fly from YYG to ORD. Timing your trip outside of the busy season is often the key to scoring lower fares.
What is the cheapest airline that flies from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from YYG to ORD, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD)?
There are no daily direct flights departing from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD). But you can opt for flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from YYG to ORD?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary depending on various factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**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 Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from YYG to ORD right before your getaway is typically more expensive. But if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a YYG to ORD flight and hotel package?
You'll generally save money by booking a YYG to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your preferred flights and accommodations, you can add extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Charlottetown Airport (YYG) to O'Hare Intl. Airport (ORD)?
If you booked your YYG to ORD flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

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*Available to One Key members.