ORD - YYG

$611 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 5/29. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$611
Typical prices: $504-$698
Air Canada
Fri 5/29Wed 6/3
ORD - YYG • 1 stop
Cheapest one-way
Multiple Airlines
Sun 2/1
ORD - YYG • multi-stop
Top airlines
Air Canada
Cheapest • from $611 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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Flight Deals
Booking Insights
Flight Deals

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

Fri, May 29 - Wed, Jun 3
Air Canada Logo
8:45 am - 3:37 pm
ORD
-
YYG
4h 52m
1 stop
Air Canada Logo
12:30 pm - 4:59 pm
YYG
-
ORD
6h 29m
1 stop
$611Air Canada
Fri, May 29 - Wed, Jun 3
Air Canada Logo
8:45 am - 3:37 pm
ORD
-
YYG
4h 52m
1 stop
Air Canada Logo
4:20 pm - 8:05 pm
YYG
-
ORD
5h 45m
1 stop
$632Air Canada
Tue, Mar 17 - Tue, Mar 24
Multiple Airlines Logo
5:05 am - 1:02 pm
ORD
-
YYG
29h 57m
3 stops
Multiple Airlines Logo
1:45 pm - 12:22 am
YYG
-
ORD
12h 37m
3 stops
$652Multiple Airlines
Thu, May 28 - Wed, Jun 3
Multiple Airlines Logo
5:30 pm - 5:10 pm
ORD
-
YYG
21h 40m
1 stop
Multiple Airlines Logo
11:40 am - 4:40 pm
YYG
-
ORD
31h 00m
2 stops
$653Multiple Airlines
Fri, May 29 - Wed, Jun 3
Air Canada Logo
8:45 am - 3:37 pm
ORD
-
YYG
4h 52m
1 stop
Air Canada Logo
12:30 pm - 4:59 pm
YYG
-
ORD
6h 29m
1 stop
$658Air Canada
Wed, Jun 10 - Mon, Jun 15
Air Canada Logo
3:45 pm - 12:02 am
ORD
-
YYG
6h 17m
1 stop
Air Canada Logo
4:20 pm - 8:05 pm
YYG
-
ORD
5h 45m
1 stop
$659Air Canada
Wed, Jun 17 - Wed, Jun 24
Air Canada Logo
8:45 am - 3:30 pm
ORD
-
YYG
4h 45m
1 stop
Air Canada Logo
11:20 am - 2:55 pm
YYG
-
ORD
5h 35m
1 stop
$665Air Canada
Thu, Apr 9 - Sun, Apr 12
Air Canada Logo
7:55 am - 5:37 pm
ORD
-
YYG
7h 42m
1 stop
Air Canada Logo
11:15 am - 2:55 pm
YYG
-
ORD
5h 40m
1 stop
$669Air Canada
Sat, Apr 11 - Sat, Apr 18
Air Canada Logo
4:15 pm - 12:22 am
ORD
-
YYG
6h 07m
1 stop
Air Canada Logo
11:15 am - 2:55 pm
YYG
-
ORD
5h 40m
1 stop
$670Air Canada
Wed, Jun 10 - Mon, Jun 15
Air Canada Logo
2:15 pm - 12:02 am
ORD
-
YYG
7h 47m
1 stop
Air Canada Logo
5:15 am - 2:53 pm
YYG
-
ORD
11h 38m
2 stops
$672Air Canada
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 ($611) and United Airlines ($750).

Good to know

Low seasonAugust
Cheapest flight$611
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 32% lower on average.
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 $611 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 $762 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 $570 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 9222 reviews
8.1Crew
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
Airline reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

2.0 MediocreJames, Jan 2026
ORD - MSP
Read more United Airlines reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

I waiting for 2 hrs to retrieve my luggage. Didn't get home till 3am.

The flight left late and I didn’t get a glass of bubbly upon boarding (which I’m used to when booking business class on other flights), but otherwise it was a pleasant flight with lovely, helpful crew members and I enjoyed my meal.

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Couldn't fit knees, only 1 toilet working, didn't get anything to drink cause the stewards were not able to get to us

Flight was canceled for a reason they knew hours before but did not mention. Next the gate chnage from 37 to 38 at least 10 times. Ridiculous.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

Our biggest complaint about Air Canada is that if you don’t like your seat during check-in, there’s a fee to move elsewhere. On our flight from YUL to FFL, we were charged to change seats—just regular seats. What’s maddening is that the plane wasn’t even full; there were even a few people sleeping in the middle row sections (entire rows, completely empty), using them as beds. In my opinion, charging passengers for seat changes is a cash grab by Air Canada. They are definitely not the airline they were back in the day. I suppose they need to gouge the consumer now that they pay their attendants while on ground. One out of 10.

Nothing specific. Cabin temperature was too high for some reason.

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

Information on your arrival and departure airports