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Cheap flights from Illinois to Charlottetown from C$ 414

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 21/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YYG
14 Jul — 21 Jul1
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 14 June 2026.

Thu 2/710:25 a.m.
MDW
-
YYG
1 stop22h 30m
Multiple Airlines
Wed 8/712:45 p.m.
YYG
-
MDW
1 stop22h 55m
Multiple Airlines
Deal found 10/6C$ 743
Thu 2/73:20 p.m.
MDW
-
YYG
2 stops41h 50m
Porter Airlines
Wed 8/712:45 p.m.
YYG
-
MDW
1 stop22h 55m
Porter Airlines
Deal found 10/6C$ 758
Fri 21/82:00 p.m.
ORD
-
YYG
3 stops19h 10m
Multiple Airlines
Tue 25/85:20 a.m.
YYG
-
ORD
2 stops11h 35m
Multiple Airlines
Deal found 10/6C$ 761
Thu 2/75:35 p.m.
ORD
-
YYG
1 stop15h 20m
Multiple Airlines
Wed 8/711:20 a.m.
YYG
-
ORD
2 stops11h 09m
Multiple Airlines
Deal found 10/6C$ 811
Fri 24/73:20 p.m.
MDW
-
YYG
1 stop18h 28m
Porter Airlines
Mon 27/712:45 p.m.
YYG
-
MDW
1 stop22h 55m
Porter Airlines
Deal found 11/6C$ 834
Fri 21/88:45 a.m.
ORD
-
YYG
1 stop4h 55m
Air Canada
Tue 25/811:20 a.m.
YYG
-
ORD
1 stop5h 35m
Air Canada
Deal found 10/6C$ 838
Thu 2/73:20 p.m.
MDW
-
YYG
2 stops23h 15m
Porter Airlines
Fri 10/711:50 a.m.
YYG
-
MDW
2 stops23h 50m
Porter Airlines
Deal found 10/6C$ 849
Fri 26/63:20 p.m.
MDW
-
YYG
2 stops17h 50m
Multiple Airlines
Wed 1/711:40 a.m.
YYG
-
MDW
1 stop24h 00m
Multiple Airlines
Deal found 11/6C$ 877
Wed 8/710:25 a.m.
MDW
-
YYG
1 stop23h 23m
Porter Airlines
Sun 12/75:20 p.m.
YYG
-
MDW
2 stops42h 20m
Porter Airlines
Deal found 13/6C$ 895
Wed 16/98:45 a.m.
ORD
-
YYG
1 stop4h 55m
Air Canada
Tue 22/94:30 p.m.
YYG
-
ORD
1 stop5h 42m
Air Canada
Deal found 10/6C$ 976
Tue 1/128:00 a.m.
ORD
-
YYG
1 stop7h 25m
Air Canada
Fri 4/1211:15 a.m.
YYG
-
ORD
1 stop5h 40m
Air Canada
Deal found 11/6C$ 982
Sun 16/88:45 a.m.
ORD
-
YYG
1 stop4h 55m
Air Canada
Sat 22/84:30 p.m.
YYG
-
ORD
1 stop5h 35m
Air Canada
Deal found 10/6C$ 985

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 14 June 2026.

Round-trip from

C$ 743

One-way from

C$ 414
Porter Airlines
  • Porter Airlines
  • 2/7-8/7
  • 2 total stops
  • 45h 25m total
  • Illinois to Charlottetown
Search Deals
Porter Airlines
  • Porter Airlines
  • 21/9
  • 2 total stops
  • 26h 50m 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 14 June 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

Fri 24/7

3:20 p.m.-11:48 a.m.

1 stop18h 28m

Charlottetown

Mon 27/7

12:45 p.m.-9:40 a.m.

1 stop22h 55m

C$ 834

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Wed 8/7

10:25 a.m.-11:48 a.m.

1 stop23h 23m

Charlottetown

Sun 12/7

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

2 stops42h 20m

C$ 895

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$ 976

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 16/9

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

1 stop4h 55m

Charlottetown

Sun 20/9

11:20 a.m.-8:29 p.m.

2 stops11h 09m

C$ 983
Quickest round-trip

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Sun 16/8

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

1 stop4h 55m

Charlottetown

Sat 22/8

4:30 p.m.-8:05 p.m.

1 stop5h 35m

C$ 985

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 2/9

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

1 stop4h 55m

Charlottetown

Mon 7/9

11:20 a.m.-8:49 p.m.

2 stops11h 29m

C$ 985

ChicagoCharlottetown

ORD - YYG

ORDYYG

Chicago O'Hare Intl

Wed 21/10

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

1 stop6h 05m

Charlottetown

Sun 25/10

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

1 stop6h 00m

C$ 989

ChicagoCharlottetown

MDW - YYG

MDWYYG

Chicago Midway

Thu 2/7

10:25 a.m.-11:10 a.m.

2 stops22h 45m

Charlottetown

Wed 8/7

11:50 a.m.-9:40 a.m.

3 stops23h 50m

C$ 1,011

St. LouisCharlottetown

STL - YYG

STLYYG

Lambert-St Louis

Sat 10/10

2:40 p.m.-11:59 p.m.

1 stop7h 19m

Charlottetown

Wed 14/10

11:20 a.m.-8:00 p.m.

2 stops10h 40m

C$ 1,052

St. LouisCharlottetown

STL - YYG

STLYYG

Lambert-St Louis

Mon 2/11

4:15 p.m.-12:05 a.m.

1 stop5h 50m

Charlottetown

Wed 4/11

5:00 a.m.-3:30 p.m.

1 stop12h 30m

C$ 1,074

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 25 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?

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 4h 55m. 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
Summerside

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