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.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest time of day to fly from NL to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Newfoundland and Labrador to Chicago as you normally would.

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.

$283+ Flights from Newfoundland and Labrador to Chicago

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Cheap flight deals from Newfoundland and Labrador to Chicago

Best flights from Newfoundland and Labrador to Chicago
Discover carefully curated flight deals from Newfoundland and Labrador to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

Wed 4/156:00 amYYT - MDW

2 stops11h 50mPorter Airlines

Sat 4/1812:45 pmMDW - YYT

2 stops7h 50mPorter Airlines

Deal found 12/10

$529

Sat 5/301:10 pmYYT - MDW

2 stops29h 44mPorter Airlines

Wed 6/39:40 amMDW - YYT

2 stops12h 18mPorter Airlines

Deal found 12/9

$655

Sat 1/246:00 amYYT - MDW

2 stops30h 35mPorter Airlines

Sat 1/3112:45 pmMDW - YYT

2 stops8h 00mPorter Airlines

Deal found 12/10

$847

Last-minute flights from Newfoundland and Labrador to Chicago
Discover last-minute flight deals from Newfoundland and Labrador to Chicago. Data last updated December 12, 2025 and is based on user searches.

Sat 1/246:00 amYYT - MDW

2 stops30h 35mPorter Airlines

Sat 1/3112:45 pmMDW - YYT

2 stops8h 00mPorter Airlines

Deal found 12/10

$847

One-way flights from Newfoundland and Labrador to Chicago
Search for one-way flight options from Newfoundland and Labrador to Chicago. Find affordable one-way fares based on user searches. Data last updated December 12, 2025.

Sat 1/246:20 amYYT - MDW

3 stops31h 55mMultiple Airlines

Deal found 12/10

$283

Sat 1/246:20 amYYT - MDW

2 stops8h 00mPorter Airlines

Deal found 12/10

$390

Find flight deals from Newfoundland and Labrador to Chicago

Round-trip from	$529 (Porter Airlines)
One-way from	$283 (Kiwi.com)

From Newfoundland and Labrador to Chicago (CHI)

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One-way flight from Newfoundland and Labrador to Chicago (CHI)

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Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/15

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Sat 4/18

12:45 pm-11:05 pm

2 stops7h 50m

$529

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 5/30

1:10 pm-4:24 pm

2 stops29h 44m

Chicago Midway

Wed 6/3

9:40 am-12:28 am

2 stops12h 18m

$655

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/24

6:00 am-10:05 am

2 stops30h 35m

Chicago Midway

Sat 1/31

12:45 pm-11:15 pm

2 stops8h 00m

$847

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/24

6:20 am-11:45 am

3 stops31h 55m

$283

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/24

6:20 am-11:50 am

2 stops8h 00m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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.

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Everything you need to know about your flight from Newfoundland and Labrador to Chicago

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Related info for your journey

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.

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Hammond

Porter

Benton Harbor

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$283+ Cheap flights from Newfoundland and Labrador to Chicago (CHI)

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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Newfoundland and Labrador to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Newfoundland and Labrador to Chicago

Best flights from Newfoundland and Labrador to ChicagoDiscover carefully curated flight deals from Newfoundland and Labrador to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

Discover carefully curated flight deals from Newfoundland and Labrador to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

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 December 12, 2025.

Round-trip from

One-way from

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Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Newfoundland and Labrador to Chicago

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?

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

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

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

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Best flights from Newfoundland and Labrador to Chicago
Discover carefully curated flight deals from Newfoundland and Labrador to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.