What is the cheapest month to book a flight from Newfoundland and Labrador to Chicago?

Currently, August is the cheapest month in which you can book a flight from Newfoundland and Labrador to Chicago (average of $245). Flying from Newfoundland and Labrador to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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.

$433+ Flights from Newfoundland and Labrador to Chicago

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Cheap flight deals from Newfoundland and Labrador to Chicago

Round-trip from	$433 (Booking.com)

From Newfoundland and Labrador to Chicago (CHI)

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Find 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 July 31, 2025.

Wed 12/106:00 amYYT - MDW

3 stops11h 50mPorter Airlines

Mon 12/1511:00 amMDW - YYT

2 stops11h 31mPorter Airlines

Deal found 7/29

$433

Wed 9/173:00 pmYYT - MDW

2 stops45h 10mWestJet

Sat 9/2011:00 amMDW - YYT

2 stops9h 26mWestJet

Deal found 7/31

$529

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 July 31, 2025.

Wed 12/106:00 amYYT - MDW

3 stops11h 50mPorter Airlines

Mon 12/1511:00 amMDW - YYT

3 stops9h 35mPorter Airlines

Deal found 7/29

$433

Wed 9/173:00 pmYYT - MDW

2 stops45h 10mWestJet

Sat 9/2011:00 amMDW - YYT

2 stops9h 26mWestJet

Deal found 7/31

$529

Cheapflights Fare Finder

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 12/10

6:00 am-3:20 pm

3 stops11h 50m

Chicago Midway

Mon 12/15

11:00 am-11:05 pm

3 stops9h 35m

$433

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 9/17

3:00 pm-9:40 am

2 stops45h 10m

Chicago Midway

Sat 9/20

11:00 am-10:56 pm

2 stops9h 26m

$529

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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.

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Porter Airlines and WestJet from Newfoundland and Labrador to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

318 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Porter Airlines

8.0

Very good

318 reviews

Porter Airlines

8.0

Very good

318 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Jul 2025

LIS - YYZ

WestJet

7.2

Good

2,978 reviews

Porter Airlines

8.0

Very good

318 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Jul 2025

LIS - YYZ

Related info for your journey

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.
What is the cheapest month to book a flight from Newfoundland and Labrador to Chicago?
Currently, August is the cheapest month in which you can book a flight from Newfoundland and Labrador to Chicago (average of $245). Flying from Newfoundland and Labrador to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Porter

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Chesterton

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$433+ 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 12/10. 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

Keep the following information in mind while searching for Newfoundland and Labrador to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

Find flight deals from Newfoundland and Labrador to Chicago

Cheapest flights from Newfoundland and Labrador to ChicagoExplore 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 July 31, 2025.

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 July 31, 2025.

Cheapflights Fare Finder

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

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Porter Airlines and WestJet from Newfoundland and Labrador to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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.

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?

What is the cheapest month to book a flight from Newfoundland and Labrador to Chicago?

Traveling to a place near Chicago?

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Alternative routes for Newfoundland and Labrador to Chicago

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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 July 31, 2025.