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Cheap flights from Illinois to Charlottetown from C$ 399

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YYG
27 Aug — 3 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Illinois to Charlottetown

Enter your travel dates to find the best prices.

Cheapest flights from Illinois to Charlottetown
Explore the most affordable flight options available from Illinois to Charlottetown. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 July 2026.

Thu 10/93:20 p.m.
MDW
-
YYG
1 stop17h 35m
Multiple Airlines
Sun 13/911:40 a.m.
YYG
-
MDW
1 stop28h 55m
Multiple Airlines
Deal found 27/7C$ 667
Tue 8/93:20 p.m.
MDW
-
YYG
1 stop17h 35m
Multiple Airlines
Sun 13/911:40 a.m.
YYG
-
MDW
1 stop28h 55m
Multiple Airlines
Deal found 27/7C$ 673
Tue 8/98:40 p.m.
ORD
-
YYG
1 stop12h 15m
Multiple Airlines
Tue 15/911:20 a.m.
YYG
-
ORD
3 stops10h 28m
Multiple Airlines
Deal found 24/7C$ 677
Thu 10/93:20 p.m.
MDW
-
YYG
1 stop17h 35m
Multiple Airlines
Mon 14/911:40 a.m.
YYG
-
MDW
1 stop28h 55m
Multiple Airlines
Deal found 27/7C$ 685
Tue 8/93:20 p.m.
MDW
-
YYG
1 stop17h 35m
Multiple Airlines
Mon 14/911:40 a.m.
YYG
-
MDW
1 stop25h 20m
Multiple Airlines
Deal found 27/7C$ 691
Thu 20/83:15 p.m.
MDW
-
YYG
1 stop17h 40m
Multiple Airlines
Mon 24/812:45 p.m.
YYG
-
MDW
1 stop23h 00m
Multiple Airlines
Deal found 27/7C$ 714
Thu 20/83:15 p.m.
MDW
-
YYG
1 stop17h 40m
Multiple Airlines
Sun 23/812:45 p.m.
YYG
-
MDW
1 stop23h 00m
Multiple Airlines
Deal found 27/7C$ 759
Tue 8/911:45 a.m.
MDW
-
YYG
1 stop21h 10m
Multiple Airlines
Tue 15/95:20 p.m.
YYG
-
MDW
2 stops19h 40m
Multiple Airlines
Deal found 27/7C$ 764
Thu 3/93:20 p.m.
MDW
-
YYG
1 stop17h 35m
Multiple Airlines
Sun 6/911:40 a.m.
YYG
-
MDW
1 stop25h 20m
Multiple Airlines
Deal found 25/7C$ 769
Sun 6/911:45 a.m.
MDW
-
YYG
1 stop21h 10m
Multiple Airlines
Sun 13/911:40 a.m.
YYG
-
MDW
1 stop25h 20m
Multiple Airlines
Deal found 27/7C$ 783
Sun 6/911:45 a.m.
MDW
-
YYG
1 stop21h 10m
Multiple Airlines
Mon 14/911:40 a.m.
YYG
-
MDW
1 stop25h 20m
Multiple Airlines
Deal found 27/7C$ 801
Sun 9/82:40 p.m.
STL
-
YYG
1 stop7h 19m
Air Canada
Mon 31/85:20 a.m.
YYG
-
STL
1 stop10h 42m
Air Canada
Deal found 25/7C$ 1,255

Find flight deals from Illinois to Charlottetown

Keep the following information in mind while searching for Illinois to Charlottetown flight deals. Data was last updated 28 July 2026.

Round-trip from

C$ 667

One-way from

C$ 399
10/9-13/9
  • 10/9-13/9
  • 2 total stops
  • 46h 30m total
  • Illinois to Charlottetown
Search Deals
Air Canada
  • Air Canada
  • 8/9
  • 1 total stop
  • 6h 29m total
  • Illinois to Charlottetown
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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, Cheapflights users made 629,999 searches. Data last updated 28 July 2026.
Use the filters below to find and compare flights from Illinois to Charlottetown that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 8/9

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

1 stop17h 35m

Charlottetown

Mon 14/9

11:40 a.m.-11:00 a.m.

1 stop25h 20m

C$ 691

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 8/9

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

3 stops17h 00m

Charlottetown

Tue 15/9

11:20 a.m.-7:48 p.m.

3 stops10h 28m

C$ 756

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Tue 8/9

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

1 stop12h 15m

Charlottetown

Tue 15/9

11:20 a.m.-2:52 p.m.

1 stop5h 32m

C$ 791

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Sun 6/9

11:45 a.m.-10:55 a.m.

1 stop21h 10m

Charlottetown

Mon 14/9

11:40 a.m.-11:00 a.m.

1 stop25h 20m

C$ 801

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 9/9

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

3 stops17h 00m

Charlottetown

Wed 16/9

11:20 a.m.-2:52 p.m.

1 stop5h 32m

C$ 905

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Tue 8/9

3:20 p.m.-4:35 p.m.

2 stops23h 15m

Charlottetown

Tue 15/9

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

2 stops19h 40m

C$ 917

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 26/8

8:05 a.m.-10:55 a.m.

2 stops48h 50m

Charlottetown

Fri 4/9

6:00 p.m.-4:40 p.m.

1 stop24h 40m

C$ 972

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 16/9

3:20 p.m.-4:35 p.m.

2 stops23h 15m

Charlottetown

Tue 22/9

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

2 stops19h 40m

C$ 980

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Fri 21/8

3:15 p.m.-4:35 p.m.

2 stops23h 20m

Charlottetown

Mon 24/8

11:45 a.m.-9:45 a.m.

2 stops24h 00m

C$ 1,008
Quickest round-trip

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 26/8

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

1 stop5h 00m

Charlottetown

Fri 4/9

5:20 a.m.-9:53 a.m.

1 stop6h 33m

C$ 1,011

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/7

Showing 1-10 of 23 resultsSorted by cheapest first
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Best time to book a flight from Illinois to Charlottetown

Have a flexible travel schedule? Discover the best time to fly to Charlottetown from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Charlottetown

How much does it cost to fly round-trip from Illinois to Charlottetown?

Airfare is below average for this route at the moment.
Illinois to Charlottetown flights typically cost between C$ 896 and C$ 1,093 in September.
The cheapest round-trip price found within the last 5 days was C$ 677 on Multiple Airlines (8 Sep-15 Sep).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Charlottetown. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Charlottetown from Illinois?

    Charlottetown (YYG) is the airport you will fly into if you book a flight from Illinois to Charlottetown. It is only a 5.3 km journey from Charlottetown (YYG) to Charlottetown’s city centre.

  • How long is the flight from Illinois to Charlottetown?

    Departing from Illinois to Charlottetown will take you 17h. Illinois and Charlottetown are separated by a distance of 2025 km. This flight may include one or multiple stops.

  • What are the most popular routes from Illinois to Charlottetown?

    Most travellers choose Chicago O'Hare Intl - Charlottetown, Chicago Midway - Charlottetown or Lambert-St Louis - Charlottetown when deciding on the best route from Illinois to Charlottetown.

  • Can I find deals for flights from Illinois to Charlottetown that include hotel bookings?

    Yes. In addition to deals on Illinois to Charlottetown flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Charlottetown?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Charlottetown.

  • Can I find deals for business class flights from Illinois to Charlottetown?

    Yes. Cheapflights offers flight deals from Illinois to Charlottetown by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Charlottetown?

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