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Cheap flights from Newfoundland and Labrador to Chicago from C$ 324

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 19/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
25 Feb — 4 Mar1
1 adult

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 20 February 2025.

Round-trip from

C$ 658

One-way from

C$ 324

Popular in

March

Cheapest in

June
6/4-13/4
  • 6/4-13/4
  • 5 total stops
  • 51h 52m total
  • Newfoundland and Labrador to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 19/4
  • 2 total stops
  • 8h 30m total
  • Newfoundland and Labrador to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 372 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals

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 20 February 2025.

Sun 6/41:05 p.m.YYT - ORD
2 stops20h 29mMultiple Airlines
Sun 13/41:47 p.m.ORD - YYT
3 stops31h 23mMultiple Airlines
Deal found 20/2C$ 658
Sun 6/46:00 a.m.YYT - MDW
2 stops13h 10mPorter Airlines
Sun 13/45:35 p.m.MDW - YYT
2 stops27h 35mPorter Airlines
Deal found 20/2C$ 733
Sun 6/45:00 a.m.YYT - ORD
1 stop7h 31mAir Canada
Sun 13/47:10 a.m.ORD - YYT
1 stop6h 42mAir Canada
Deal found 20/2C$ 743
Sun 16/35:00 a.m.YDF - ORD
1 stop7h 34mMultiple Airlines
Wed 19/32:05 p.m.ORD - YDF
1 stop9h 20mMultiple Airlines
Deal found 20/2C$ 864
Sun 6/45:40 a.m.YYT - ORD
1 stop7h 37mUnited Airlines
Sun 13/48:45 a.m.ORD - YYT
2 stops14h 19mUnited Airlines
Deal found 20/2C$ 901
Sun 16/36:00 a.m.YDF - ORD
2 stops8h 39mAir Canada
Wed 19/37:10 a.m.ORD - YDF
2 stops9h 19mAir Canada
Deal found 20/2C$ 1,061
Fri 18/44:25 p.m.YYT - MDW
2 stops22h 05mMultiple Airlines
Sat 26/47:00 p.m.MDW - YYT
2 stops49h 25mMultiple Airlines
Deal found 18/2C$ 1,159

Find flights from Newfoundland and Labrador to Chicago within your budget

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 629,999 searches. Data last updated 20 February 2025.

Fly from

Newfoundland and Labrador

Fly to

Chicago

Route

Depart

Return

Price

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 6/4

1:05 p.m.-7:04 a.m.

2 stops20h 29m

Chicago O'Hare Intl

Sun 13/4

1:47 p.m.-11:40 p.m.

3 stops31h 23m

C$ 658

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 6/4

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

2 stops13h 10m

Chicago Midway

Sun 13/4

5:35 p.m.-11:40 p.m.

2 stops27h 35m

C$ 733

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 6/4

5:00 a.m.-10:01 a.m.

1 stop7h 31m

Chicago O'Hare Intl

Sun 13/4

7:10 a.m.-4:22 p.m.

1 stop6h 42m

C$ 743

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sun 16/3

5:00 a.m.-10:04 a.m.

1 stop7h 34m

Chicago O'Hare Intl

Wed 19/3

2:05 p.m.-1:55 a.m.

1 stop9h 20m

C$ 864

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 6/4

5:40 a.m.-10:47 a.m.

1 stop7h 37m

Chicago O'Hare Intl

Sun 13/4

8:45 a.m.-1:34 a.m.

2 stops14h 19m

C$ 901

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sun 16/3

6:00 a.m.-12:09 p.m.

2 stops8h 39m

Chicago O'Hare Intl

Wed 19/3

7:10 a.m.-6:59 p.m.

2 stops9h 19m

C$ 1,061

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 18/4

4:25 p.m.-12:00 p.m.

2 stops22h 05m

Chicago Midway

Sat 26/4

7:00 p.m.-10:55 p.m.

2 stops49h 25m

C$ 1,159

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 19/4

6:00 a.m.-12:00 p.m.

2 stops8h 30m

C$ 324

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 19/4

5:00 a.m.-10:01 a.m.

1 stop7h 31m

C$ 500

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 18/4

5:40 a.m.-1:15 p.m.

2 stops10h 05m

C$ 513

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/2

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.

Travel insights for flights from Newfoundland and Labrador to Chicago

Get recent, data-driven insights about flights from Newfoundland and Labrador to Chicago including ideal travel times, pricing trends, and more.

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

Find hourly flight availability from Newfoundland and Labrador to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 20 February 2025.

When flying from Newfoundland and Labrador to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 20 February 2025.
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Overall

7.9

Boarding

8.2

Entertainment

6.9

Food

7.6

Comfort

8.0

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Porter Airlines
7.9
Good
276 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Overall

7.9

Boarding

8.2

Entertainment

6.9

Food

7.6

Comfort

8.0

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

United Airlines
7.4
Good
8,765 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Overall

7.9

Boarding

8.2

Entertainment

6.9

Food

7.6

Comfort

8.0

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Air Canada
7.0
Good
8,748 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Overall

7.9

Boarding

8.2

Entertainment

6.9

Food

7.6

Comfort

8.0

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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.

  • What are the cheapest airlines to fly from Newfoundland and Labrador to Chicago one-way?

    To fly one-way, consider booking your trip with Porter Airlines, which is currently one of the cheapest options available, starting at C$ 324. Air Canada flights start at C$ 500 while deals on United Airlines start at C$ 513 one-way.

  • What are the most popular routes from Newfoundland and Labrador to Chicago?

    While some choose either Deer Lake - Chicago O'Hare Intl or St John's - Chicago O'Hare Intl, St John's - Chicago Midway is the most popular route from Newfoundland and Labrador to Chicago.

  • 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, January is the cheapest month in which you can book a flight from Newfoundland and Labrador to Chicago (average of C$ 261). Flying from Newfoundland and Labrador to Chicago in March is currently the most expensive (average of C$ 355). 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.

See more FAQs

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Alternative routes for Newfoundland and Labrador to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Newfoundland and Labrador to Chicago

Discover the top airline that operate flights from Newfoundland and Labrador to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 20 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 651AverageC$ 779FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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How does Cheapflights help users find flights from Newfoundland and Labrador to Chicago?

When you search for this flight from Newfoundland and Labrador to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Newfoundland and Labrador to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Newfoundland and Labrador to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Newfoundland and Labrador to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Newfoundland and Labrador shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Newfoundland and Labrador to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Newfoundland and Labrador today and book when prices fit your budget.

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