$210 Cheap Flights from Charlottetown (YYG) to Chicago (ORD)

View $210 flight on Mon, Oct 20, 2025Opens in a new window

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

Cheap Flights from Charlottetown to Chicago (YYG-ORD)

Prices were available within the past 7 days and start at $210 for one-way flights and $464 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Oct 8 - Wed, Oct 15
YYG
Charlottetown
ORD
Chicago
$464 Roundtrip, found 4 days ago
$464
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Oct 8 from Charlottetown to Chicago, returning Wed, Oct 15, priced at $464 found 4 days ago
Air Canada
Sat, Oct 11 - Sun, Oct 12
YYG
Charlottetown
ORD
Chicago
$469 Roundtrip, found 4 days ago
$469
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Oct 11 from Charlottetown to Chicago, returning Sun, Oct 12, priced at $469 found 4 days ago
Air Canada
Wed, Oct 8 - Wed, Oct 15
YYG
Charlottetown
ORD
Chicago
$479 Roundtrip, found 4 days ago
$479
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Oct 8 from Charlottetown to Chicago, returning Wed, Oct 15, priced at $479 found 4 days ago
Air Canada
Sat, Oct 4 - Tue, Oct 7
YYG
Charlottetown
ORD
Chicago
$485 Roundtrip, found 4 days ago
$485
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Oct 4 from Charlottetown to Chicago, returning Tue, Oct 7, priced at $485 found 4 days ago
Air Canada
Wed, Oct 8 - Wed, Oct 15
YYG
Charlottetown
ORD
Chicago
$487 Roundtrip, found 4 days ago
$487
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Oct 8 from Charlottetown to Chicago, returning Wed, Oct 15, priced at $487 found 4 days ago
Air Canada
Sun, Oct 5 - Wed, Oct 8
YYG
Charlottetown
ORD
Chicago
$502 Roundtrip, found 4 days ago
$502
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sun, Oct 5 from Charlottetown to Chicago, returning Wed, Oct 8, priced at $502 found 4 days ago
Air Canada
Sun, Oct 5 - Tue, Oct 14
YYG
Charlottetown
ORD
Chicago
$509 Roundtrip, found 4 days ago
$509
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sun, Oct 5 from Charlottetown to Chicago, returning Tue, Oct 14, priced at $509 found 4 days ago
Air Canada
Wed, Oct 8 - Wed, Oct 15
YYG
Charlottetown
ORD
Chicago
$514 Roundtrip, found 4 days ago
$514
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Oct 8 from Charlottetown to Chicago, returning Wed, Oct 15, priced at $514 found 4 days ago
United
Wed, Oct 8 - Wed, Oct 15
YYG
Charlottetown
ORD
Chicago
$537 Roundtrip, found 4 days ago
$537
Roundtrip
found 4 days ago
Select United flight, departing Wed, Oct 8 from Charlottetown to Chicago, returning Wed, Oct 15, priced at $537 found 4 days ago
Air Canada
Wed, Sep 10 - Wed, Sep 17
YYG
Charlottetown
ORD
Chicago
$554 Roundtrip, found 1 day ago
$554
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Sep 10 from Charlottetown to Chicago, returning Wed, Sep 17, priced at $554 found 1 day ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $554
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $554
Flights from Charlottetown (YYG) to Chicago (ORD)
Origin airport
Charlottetown
Destination airport
O'Hare Intl.
Roundtrip price
$463
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 October. 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 $210 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 $210 or cheap return flight from $464 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)?
October 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.