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Cheap flights from Chicago to Charlottetown from C$ 492

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Charlottetown departing on 29/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to Charlottetown

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:20 p.m. - 10:55 a.m.MDW  Chicago Midway-YYG Charlottetown
17h 35m1 stop Toronto Island
Multiple Airlines Logo
5:20 p.m. - 11:00 a.m.YYG  Charlottetown-MDW Chicago Midway
19h 40m2 stops Ottawa Toronto Pearson Intl
C$ 670Multiple Airlines
Sat, 19 Sep - Sat, 26 Sep
Multiple Airlines Logo
5:35 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
20h 05m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
11:40 a.m. - 7:48 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
10h 08m1 stop Toronto Pearson Intl
C$ 771Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
8:40 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
17h 00m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
11:40 a.m. - 8:12 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
10h 32m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 785Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
5:35 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
20h 05m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
11:40 a.m. - 7:48 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
10h 08m1 stop Toronto Pearson Intl
C$ 791Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
8:40 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
17h 00m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
11:40 a.m. - 8:12 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
10h 32m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 796Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
3:40 p.m. - 10:55 a.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
17h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Multiple Airlines Logo
12:30 p.m. - 4:58 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
6h 28m1 stop Toronto Pearson Intl
C$ 805Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct
Multiple Airlines Logo
8:40 p.m. - 10:55 a.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
12h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
5:25 a.m. - 9:00 a.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
5h 35m1 stop Toronto Pearson Intl
C$ 809Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct
Multiple Airlines Logo
3:45 p.m. - 10:30 a.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
16h 45m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
11:40 a.m. - 7:48 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
10h 08m1 stop Toronto Pearson Intl
C$ 818Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
7:25 a.m. - 4:35 p.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
7h 10m1 stop Toronto Island
Multiple Airlines Logo
11:40 a.m. - 7:48 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
10h 08m1 stop Toronto Pearson Intl
C$ 825Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
3:40 p.m. - 10:55 a.m.ORD  Chicago O'Hare Intl-YYG Charlottetown
17h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Multiple Airlines Logo
12:30 p.m. - 4:58 p.m.YYG  Charlottetown-ORD Chicago O'Hare Intl
6h 28m1 stop Toronto Pearson Intl
C$ 827Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct

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Air Canada flights from Chicago to Charlottetown

Our best Air Canada deals on Chicago to Charlottetown flight tickets
Air Canada
28 Sep
ORD8:40 p.m.Chicago O'Hare Intl
17h 00m
3 stops
YYG3:40 p.m.Charlottetown
5 Oct
YYG11:20 a.m.Charlottetown
11h 09m
2 stops
ORD8:29 p.m.Chicago O'Hare Intl
C$ 838
Air Canada
28 Sep
ORD5:35 p.m.Chicago O'Hare Intl
20h 05m
3 stops
YYG3:40 p.m.Charlottetown
5 Oct
YYG12:05 p.m.Charlottetown
6h 53m
1 stop
ORD4:58 p.m.Chicago O'Hare Intl
C$ 853
Air Canada
30 Sep
ORD8:40 p.m.Chicago O'Hare Intl
12h 30m
1 stop
YYG11:10 a.m.Charlottetown
7 Oct
YYG11:20 a.m.Charlottetown
11h 09m
2 stops
ORD8:29 p.m.Chicago O'Hare Intl
C$ 877

Porter Airlines flights from Chicago to Charlottetown

Our best Porter Airlines deals on Chicago to Charlottetown flight tickets
Porter Airlines
28 Sep
MDW3:20 p.m.Chicago Midway
23h 15m
2 stops
YYG4:35 p.m.Charlottetown
5 Oct
YYG5:20 p.m.Charlottetown
19h 40m
2 stops
MDW11:00 a.m.Chicago Midway
C$ 860
Porter Airlines
28 Sep
MDW3:20 p.m.Chicago Midway
23h 15m
2 stops
YYG4:35 p.m.Charlottetown
5 Oct
YYG5:20 p.m.Charlottetown
19h 40m
2 stops
MDW11:00 a.m.Chicago Midway
C$ 871
Porter Airlines
28 Sep
MDW3:20 p.m.Chicago Midway
23h 15m
2 stops
YYG4:35 p.m.Charlottetown
5 Oct
YYG5:20 p.m.Charlottetown
19h 40m
2 stops
MDW11:00 a.m.Chicago Midway
C$ 874

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Charlottetown that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 17 August 2026.
Use the filters below to find and compare flights from Chicago to Charlottetown that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCharlottetown

MDW Chicago Midway - YYG Charlottetown

MDWYYG

Chicago Midway

Sat 19/9

3:20 p.m.-10:55 a.m.

1 stop17h 35m

Charlottetown

Sat 26/9

5:20 p.m.-11:00 a.m.

2 stops19h 40m

C$ 670

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Mon 28/9

5:35 p.m.-3:40 p.m.

3 stops20h 05m

Charlottetown

Mon 5/10

11:40 a.m.-7:48 p.m.

1 stop10h 08m

C$ 771

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Mon 28/9

8:40 p.m.-3:40 p.m.

3 stops17h 00m

Charlottetown

Mon 5/10

11:40 a.m.-8:12 p.m.

2 stops10h 32m

C$ 785

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Mon 28/9

5:35 p.m.-3:40 p.m.

3 stops20h 05m

Charlottetown

Mon 5/10

11:40 a.m.-7:48 p.m.

1 stop10h 08m

C$ 791

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Mon 28/9

8:40 p.m.-3:40 p.m.

3 stops17h 00m

Charlottetown

Mon 5/10

11:40 a.m.-8:12 p.m.

2 stops10h 32m

C$ 796

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Sun 27/9

3:40 p.m.-10:55 a.m.

2 stops17h 15m

Charlottetown

Sun 4/10

12:30 p.m.-4:58 p.m.

1 stop6h 28m

C$ 805

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Sun 27/9

8:40 p.m.-10:55 a.m.

1 stop12h 15m

Charlottetown

Sun 4/10

5:25 a.m.-9:00 a.m.

1 stop5h 35m

C$ 809

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Mon 28/9

3:45 p.m.-10:30 a.m.

2 stops16h 45m

Charlottetown

Mon 5/10

11:40 a.m.-7:48 p.m.

1 stop10h 08m

C$ 818
Quickest round-trip

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Mon 28/9

7:25 a.m.-4:35 p.m.

1 stop7h 10m

Charlottetown

Mon 5/10

11:40 a.m.-7:48 p.m.

1 stop10h 08m

C$ 825

ChicagoCharlottetown

ORD Chicago O'Hare Intl - YYG Charlottetown

ORDYYG

Chicago O'Hare Intl

Sun 27/9

3:40 p.m.-10:55 a.m.

2 stops17h 15m

Charlottetown

Sun 4/10

12:30 p.m.-4:58 p.m.

1 stop6h 28m

C$ 827

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago to Charlottetown

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Charlottetown?

The cheapest month to fly to Charlottetown from Chicago is in October. Flight prices, which tend to average around C$ 0, are often lower during this time because this is during the off-season. If you’re not able to fly to Charlottetown in October, then February is your next best option. Flight prices from Chicago to Charlottetown during February average around C$ 0.

When to book flights from Chicago to Charlottetown

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Charlottetown according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Charlottetown (CHI to YYG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Charlottetown

Best price found

C$ 492

Fastest flight time

6h 14m

Direct flights

None
The best one-way flight to Charlottetown from Chicago in the past 72 hours is C$ 492. The best round-trip flight deal from Chicago to Charlottetown found on momondo in the last 72 hours is C$ 670.
The fastest flight from Chicago to Charlottetown takes 6h 14m
There are no direct flights from Chicago to Charlottetown. There are no popular flight routes from Chicago to Charlottetown.
Search flight deals

Frequently asked questions about flying from Chicago to Charlottetown

  • How far is Chicago to Charlottetown by plane?

    A flight from Chicago to Charlottetown will travel around 2006.7 km. Flights usually cover this in 6h 14m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Charlottetown Airport?

    Prices for flights from Chicago to Charlottetown Airport are updated daily.

  • How old do you have to be to fly from Chicago to Charlottetown Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Charlottetown Airport.

  • What documentation or ID do you need to fly to Charlottetown Airport?

    The necessary travel and health documents for your Charlottetown Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Charlottetown?

Book flights to Charlottetown if you plan to visit one of these locations
Summerside
Cornwall
Pictou

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Charlottetown?

It is quick and easy to find Chicago to Charlottetown flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Charlottetown that suits you.

Can I find flights from Chicago to Charlottetown with flexible booking policies on momondo?

All flight searches from Chicago to Charlottetown on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Charlottetown?

momondo helps you find the best flight between Chicago and Charlottetown by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Charlottetown right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Charlottetown flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cabin classes currently available on flights to Charlottetown

List of cabin classes available on flights landing in Charlottetown. Availability may vary depending on flight origin and airline.
First Class to Charlottetown
Business Class to Charlottetown