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$438+ Cheap flights from Newfoundland and Labrador to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
مارس 1 — مارس 81
ح 3/1
ح 3/8
1 adult, Economy
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Cheap flight deals from Newfoundland and Labrador to Chicago

Cheapest flights from Newfoundland and Labrador to Chicago
Explore the most affordable flight options available from Newfoundland and Labrador to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on يناير 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
خ 4/236:20 am
YYT
-
MDW
2 stops30h 15m
Multiple Airlines
ح 4/2611:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/29$438
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ج 4/246:20 am
YYT
-
MDW
2 stops11h 30m
Multiple Airlines
ن 4/2711:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/29$463
This Trip.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
خ 4/236:00 am
YYT
-
MDW
2 stops11h 50m
Porter Airlines
ن 4/2711:00 am
MDW
-
YYT
2 stops9h 35m
Porter Airlines
Deal found 1/29$465
This FlightHub deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ج 4/246:20 am
YYT
-
MDW
2 stops11h 30m
Porter Airlines
ن 4/2711:00 am
MDW
-
YYT
2 stops9h 35m
Porter Airlines
Deal found 1/29$467
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ج 4/245:40 pm
YYT
-
MDW
1 stop20h 40m
Multiple Airlines
ث 4/284:15 pm
MDW
-
YYT
1 stop28h 10m
Multiple Airlines
Deal found 1/29$490
This Porter Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 2/146:00 am
YYT
-
MDW
2 stops8h 25m
Porter Airlines
ر 2/1811:05 am
MDW
-
YYT
2 stops11h 26m
Porter Airlines
Deal found 1/27$515

Find flight deals from Newfoundland and Labrador to Chicago

Keep the following information in mind while searching for Newfoundland and Labrador to Chicago flight deals. Data was last updated يناير 30, 2026.

Round-trip from

$438
(Kiwi.com)
From Newfoundland and Labrador to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Newfoundland and Labrador to Chicago 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 2,558,603 searches. Data last updated يناير 30, 2026.
Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago that are best for you.

Fly from

Newfoundland and Labrador

Fly to

Chicago

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

خ 4/23

6:20 am-10:05 am

2 stops30h 15m

Chicago Midway

ح 4/26

11:00 am-10:55 pm

1 stop9h 25m

$438

St. John'sChicago

YYT - MDW

YYTMDW

St John's

ج 4/24

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ح 4/26

11:00 am-10:55 pm

1 stop9h 25m

$463

St. John'sChicago

YYT - MDW

YYTMDW

St John's

ج 4/24

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ن 4/27

11:00 am-10:55 pm

1 stop9h 25m

$463

St. John'sChicago

YYT - MDW

YYTMDW

St John's

خ 4/23

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

ن 4/27

11:00 am-11:05 pm

2 stops9h 35m

$465

St. John'sChicago

YYT - MDW

YYTMDW

St John's

خ 4/23

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ح 4/26

11:00 am-1:01 am

2 stops11h 31m

$465

St. John'sChicago

YYT - MDW

YYTMDW

St John's

ج 4/24

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ح 4/26

11:00 am-1:01 am

2 stops11h 31m

$465

St. John'sChicago

YYT - MDW

YYTMDW

St John's

ج 4/24

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ث 4/28

4:15 pm-10:55 pm

1 stop28h 10m

$465

St. John'sChicago

YYT - MDW

YYTMDW

St John's

خ 4/23

4:15 pm-10:05 am

2 stops20h 20m

Chicago Midway

ث 4/28

4:15 pm-10:55 pm

1 stop28h 10m

$465

St. John'sChicago

YYT - MDW

YYTMDW

St John's

ج 4/24

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ن 4/27

11:00 am-11:05 pm

2 stops9h 35m

$467

St. John'sChicago

YYT - MDW

YYTMDW

St John's

خ 4/23

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

ث 4/28

11:00 am-11:05 pm

2 stops9h 35m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 11 results
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Best time to book a flight from Newfoundland and Labrador to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Newfoundland and Labrador 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 Newfoundland and Labrador to Chicago
No data available for this route at this time. Please check back soon.

Related info for your journey

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

  • How long is the flight from Newfoundland and Labrador to Chicago?

    Departing from Newfoundland and Labrador to Chicago will take you 11h 50m. The distance from Newfoundland and Labrador to Chicago is about 1748 mi.

  • Can I find deals for flights from Newfoundland and Labrador to Chicago that include hotel bookings?

    Yes. In addition to deals on Newfoundland and Labrador to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Newfoundland and Labrador to Chicago?

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

  • Can I find deals for business class flights from Newfoundland and Labrador to Chicago?

    Yes. Cheapflights offers flight deals from Newfoundland and Labrador to Chicago 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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