ORD - YYG

$523 Find Cheap Flights from Chicago to Charlottetown

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Charlottetown departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Charlottetown

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Charlottetown, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Charlottetown, as well as popular online travel agencies
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Cheap Flights from Chicago to Charlottetown (ORD-YYG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Charlottetown that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Charlottetown

Wed, Aug 20 - Wed, Aug 27
Air Canada Logo
8:40 am - 3:30 pmORD-YYG
4h 50m1 stop
Air Canada Logo
4:20 pm - 8:16 pmYYG-ORD
5h 56m1 stop
$523Air Canada
Find Deal
Wed, Aug 20 - Wed, Aug 27
Air Canada Logo
8:40 am - 3:30 pmORD-YYG
4h 50m1 stop
Air Canada Logo
11:25 am - 7:29 pmYYG-ORD
10h 04m2 stops
$535Air Canada
Find Deal
Tue, Sep 2 - Sat, Sep 6
 Logo
6:56 am - 11:10 amORD-YYG
26h 14m2 stops
 Logo
6:40 am - 10:48 pmYYG-ORD
18h 08m3 stops
Mon, Sep 15 - Mon, Sep 22
Air Canada Logo
8:40 am - 3:32 pmORD-YYG
4h 52m1 stop
Air Canada Logo
4:20 pm - 8:11 pmYYG-ORD
5h 51m1 stop
$570Air Canada
Find Deal
Sun, Aug 24 - Wed, Aug 27
Air Canada Logo
8:40 am - 3:30 pmORD-YYG
4h 50m1 stop
Air Canada Logo
4:20 pm - 8:16 pmYYG-ORD
5h 56m1 stop
$571Air Canada
Find Deal
Sat, Aug 23 - Wed, Aug 27
Air Canada Logo
3:50 pm - 12:04 amORD-YYG
6h 14m1 stop
Air Canada Logo
4:20 pm - 8:16 pmYYG-ORD
5h 56m1 stop
$577Air Canada
Find Deal
Wed, Aug 20 - Wed, Aug 27
Air Canada Logo
8:25 pm - 10:30 amORD-YYG
12h 05m2 stops
Air Canada Logo
11:25 am - 7:29 pmYYG-ORD
10h 04m2 stops
$580Air Canada
Find Deal
Tue, Sep 2 - Sat, Sep 6
United Airlines Logo
10:55 am - 11:38 amORD-YYG
22h 43m2 stops
United Airlines Logo
4:15 pm - 8:11 pmYYG-ORD
5h 56m1 stop
$673United Airlines
Find Deal
Mon, Aug 25 - Fri, Aug 29
United Airlines Logo
8:40 am - 3:30 pmORD-YYG
4h 50m1 stop
United Airlines Logo
5:25 am - 9:55 amYYG-ORD
6h 30m1 stop
$674United Airlines
Find Deal
Mon, Aug 25 - Thu, Aug 28
United Airlines Logo
9:31 pm - 3:30 pmORD-YYG
15h 59m2 stops
United Airlines Logo
4:20 pm - 8:16 pmYYG-ORD
5h 56m1 stop
$677United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Charlottetown flights

Get data-powered insights and trends into flights from Chicago to Charlottetown to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Chicago to Charlottetown?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Charlottetown were found on Air Canada ($523) and United Airlines ($673).

Good to know

Cheapest flight$523
Flight from Chicago to Charlottetown

When to book flights from Chicago to Charlottetown

Are your dates flexible? Find out the best times to travel from Chicago to Charlottetown based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Charlottetown flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Charlottetown?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Charlottetown was $523 for a round-trip ticket.

  • Do I need a passport to fly between Chicago and Charlottetown?

    A passport is required to fly from Chicago to Charlottetown.

  • Which airports will I be using when flying from Chicago to Charlottetown?

    On your way to Charlottetown, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Charlottetown.

  • Which aircraft models fly most regularly from Chicago to Charlottetown?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Charlottetown?

    Star Alliance is the only airline alliance operating flights between Chicago and Charlottetown.

  • Which is the best airline for flights from Chicago to Charlottetown, United Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Chicago to Charlottetown are United Airlines and Air Canada. With an average price for the route of $735 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of $555 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Charlottetown?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Charlottetown.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Charlottetown?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Charlottetown from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Charlottetown?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Charlottetown with an airline and back to Chicago with another airline. Booking your flights between Chicago and YYG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Charlottetown?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Charlottetown from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Charlottetown

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Charlottetown. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Charlottetown? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8900 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Both flights are delayed so I rate the whole experience as mediocre.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

I am very tall. All airline seats are a bit uncomfortable.

Everything you need to know for your flight from Chicago to Charlottetown

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