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Cheap flights from Chicago to Charlottetown from C$ 386

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 28/5. 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

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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
-
YYG
17h 35m
1 stop
Multiple Airlines Logo
5:15 p.m. - 9:35 a.m.
YYG
-
MDW
18h 20m
2 stops
C$ 795Multiple Airlines
Thu, 28 May - Tue, 2 Jun
Air Canada Logo
8:35 a.m. - 3:40 p.m.
ORD
-
YYG
5h 05m
1 stop
Air Canada Logo
5:20 a.m. - 9:00 a.m.
YYG
-
ORD
5h 40m
1 stop
C$ 810Air Canada
Sun, 28 Jun - Sun, 5 Jul
Air Canada Logo
8:45 a.m. - 3:40 p.m.
ORD
-
YYG
4h 55m
1 stop
Air Canada Logo
4:30 p.m. - 8:12 p.m.
YYG
-
ORD
5h 42m
1 stop
C$ 892Air Canada
Wed, 16 Sep - Tue, 22 Sep
Air Canada Logo
8:45 a.m. - 3:40 p.m.
ORD
-
YYG
4h 55m
1 stop
Air Canada Logo
11:20 a.m. - 8:16 p.m.
YYG
-
ORD
10h 56m
2 stops
C$ 899Air Canada
Wed, 16 Sep - Tue, 22 Sep
Air Canada Logo
9:50 a.m. - 5:55 p.m.
ORD
-
YYG
6h 05m
1 stop
Air Canada Logo
11:20 a.m. - 8:16 p.m.
YYG
-
ORD
10h 56m
2 stops
C$ 906Air Canada
Sat, 17 Oct - Wed, 21 Oct
Air Canada Logo
8:45 a.m. - 3:40 p.m.
ORD
-
YYG
4h 55m
1 stop
Air Canada Logo
11:20 a.m. - 2:55 p.m.
YYG
-
ORD
5h 35m
1 stop
C$ 913Air Canada
Sat, 29 Aug - Sun, 6 Sep
Porter Airlines Logo
3:20 p.m. - 12:04 p.m.
MDW
-
YYG
18h 44m
1 stop
Porter Airlines Logo
5:20 p.m. - 9:40 a.m.
YYG
-
MDW
18h 20m
2 stops
C$ 922Porter Airlines
Tue, 14 Jul - Tue, 21 Jul
Multiple Airlines Logo
8:40 p.m. - 10:55 a.m.
ORD
-
YYG
12h 15m
1 stop
Multiple Airlines Logo
5:20 p.m. - 9:00 a.m.
YYG
-
ORD
17h 40m
2 stops
C$ 929Multiple Airlines
Sun, 28 Jun - Sun, 5 Jul
Porter Airlines Logo
3:20 p.m. - 12:04 p.m.
MDW
-
YYG
18h 44m
1 stop
Porter Airlines Logo
1:00 p.m. - 9:40 a.m.
YYG
-
MDW
22h 40m
1 stop
C$ 933Porter Airlines
Tue, 14 Jul - Tue, 21 Jul
Porter Airlines Logo
3:20 p.m. - 12:04 p.m.
MDW
-
YYG
18h 44m
1 stop
Porter Airlines Logo
5:20 p.m. - 9:40 a.m.
YYG
-
MDW
18h 20m
2 stops
C$ 938Porter Airlines
Tue, 14 Jul - Mon, 20 Jul

Porter Airlines flights from Chicago to Charlottetown

Our best Porter Airlines deals on Chicago to Charlottetown flight tickets
Porter Airlines
14 Jul
MDW3:20 p.m.Chicago Midway
18h 44m
1 stop
YYG12:04 p.m.Charlottetown
21 Jul
YYG5:20 p.m.Charlottetown
18h 20m
2 stops
MDW9:40 a.m.Chicago Midway
C$ 922
Porter Airlines
14 Jul
MDW3:20 p.m.Chicago Midway
18h 44m
1 stop
YYG12:04 p.m.Charlottetown
21 Jul
YYG1:00 p.m.Charlottetown
22h 40m
1 stop
MDW9:40 a.m.Chicago Midway
C$ 933
Porter Airlines
14 Jul
MDW3:20 p.m.Chicago Midway
18h 44m
1 stop
YYG12:04 p.m.Charlottetown
20 Jul
YYG5:20 p.m.Charlottetown
18h 20m
2 stops
MDW9:40 a.m.Chicago Midway
C$ 938

United Airlines flights from Chicago to Charlottetown

Our best United Airlines deals on Chicago to Charlottetown flight tickets
United Airlines
11 Sep
ORD7:45 p.m.Chicago O'Hare Intl
17h 55m
2 stops
YYG3:40 p.m.Charlottetown
13 Sep
YYG11:20 a.m.Charlottetown
5h 32m
1 stop
ORD2:52 p.m.Chicago O'Hare Intl
C$ 1,039
United Airlines
10 Sep
ORD8:00 a.m.Chicago O'Hare Intl
13h 59m
2 stops
YYG11:59 p.m.Charlottetown
13 Sep
YYG4:30 p.m.Charlottetown
5h 42m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
C$ 1,045
United Airlines
29 Aug
ORD7:45 p.m.Chicago O'Hare Intl
17h 55m
2 stops
YYG3:40 p.m.Charlottetown
6 Sep
YYG11:20 a.m.Charlottetown
5h 35m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
C$ 1,060

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 16 May 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 - YYG

MDWYYG

Chicago Midway

Thu 28/5

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

1 stop17h 35m

Charlottetown

Tue 2/6

5:15 p.m.-9:35 a.m.

2 stops18h 20m

C$ 795

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 28/6

8:35 a.m.-3:40 p.m.

1 stop5h 05m

Charlottetown

Sun 5/7

5:20 a.m.-9:00 a.m.

1 stop5h 40m

C$ 810

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 16/9

8:45 a.m.-3:40 p.m.

1 stop4h 55m

Charlottetown

Tue 22/9

4:30 p.m.-8:12 p.m.

1 stop5h 42m

C$ 892

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 16/9

8:45 a.m.-3:40 p.m.

1 stop4h 55m

Charlottetown

Tue 22/9

11:20 a.m.-8:16 p.m.

2 stops10h 56m

C$ 899

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 17/10

9:50 a.m.-5:55 p.m.

1 stop6h 05m

Charlottetown

Wed 21/10

11:20 a.m.-8:16 p.m.

2 stops10h 56m

C$ 906
Quickest round-trip

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sat 29/8

8:45 a.m.-3:40 p.m.

1 stop4h 55m

Charlottetown

Sun 6/9

11:20 a.m.-2:55 p.m.

1 stop5h 35m

C$ 913

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 14/7

3:20 p.m.-12:04 p.m.

1 stop18h 44m

Charlottetown

Tue 21/7

5:20 p.m.-9:40 a.m.

2 stops18h 20m

C$ 922

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 28/6

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

1 stop12h 15m

Charlottetown

Sun 5/7

5:20 p.m.-9:00 a.m.

2 stops17h 40m

C$ 929

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 14/7

3:20 p.m.-12:04 p.m.

1 stop18h 44m

Charlottetown

Tue 21/7

1:00 p.m.-9:40 a.m.

1 stop22h 40m

C$ 933

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 14/7

3:20 p.m.-12:04 p.m.

1 stop18h 44m

Charlottetown

Mon 20/7

5:20 p.m.-9:40 a.m.

2 stops18h 20m

C$ 938

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Charlottetown from

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 February. 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 February, then August is your next best option. Flight prices from Chicago to Charlottetown during August average around C$ 324.

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

Fastest flight time

4h 55m

Direct flights

None
The fastest flight from Chicago to Charlottetown takes 4h 55m
There are no direct flights from Chicago to Charlottetown. There are no popular flight routes from Chicago to Charlottetown.
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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 4h 55m, 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