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Cheap flights from Newfoundland and Labrador to Chicago from C$ 386

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
7 Apr — 14 Apr1
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 2 April 2025.

Round-trip from

C$ 553

One-way from

C$ 386

Popular in

March

Cheapest in

June

Average price

C$ 1,103
Porter Airlines
  • Porter Airlines
  • 30/4-7/5
  • 4 total stops
  • 24h 28m total
  • Newfoundland and Labrador to Chicago
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Air Canada
  • Air Canada
  • 1/5
  • 1 total stop
  • 16h 22m total
  • Newfoundland and Labrador to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 380 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 45 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 2 April 2025.

Wed 30/46:00 a.m.YYT - MDW
2 stops13h 10mPorter Airlines
Wed 7/59:40 a.m.MDW - YYT
2 stops11h 18mPorter Airlines
Deal found 1/4C$ 553
Wed 7/58:05 a.m.YDF - ORD
2 stops13h 55mAir Canada
Mon 12/54:00 p.m.ORD - YDF
1 stop6h 21mAir Canada
Deal found 2/4C$ 610
Mon 12/52:00 p.m.YYT - ORD
1 stop8h 42mMultiple Airlines
Wed 21/56:19 p.m.ORD - YYT
2 stops16h 13mMultiple Airlines
Deal found 1/4C$ 627
Mon 12/55:45 a.m.YYT - ORD
1 stop6h 37mAir Canada
Wed 21/56:11 p.m.ORD - YYT
1 stop16h 21mAir Canada
Deal found 1/4C$ 633
Wed 30/41:05 p.m.YYT - MDW
2 stops22h 10mMultiple Airlines
Wed 7/59:40 a.m.MDW - YYT
1 stop10h 45mMultiple Airlines
Deal found 1/4C$ 636
Sat 26/41:05 p.m.YYT - ORD
2 stops21h 00mUnited Airlines
Mon 28/47:00 a.m.ORD - YYT
2 stops16h 47mUnited Airlines
Deal found 1/4C$ 705
Wed 7/55:25 a.m.YDF - ORD
1 stop9h 08mMultiple Airlines
Mon 12/54:00 p.m.ORD - YDF
1 stop6h 21mMultiple Airlines
Deal found 1/4C$ 715
Wed 30/43:00 p.m.YYT - ORD
2 stops19h 12mDelta
Wed 7/511:03 a.m.ORD - YYT
2 stops9h 22mDelta
Deal found 1/4C$ 788

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 629,999 searches. Data last updated 2 April 2025.
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

Wed 30/4

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

2 stops13h 10m

Chicago Midway

Wed 7/5

9:40 a.m.-11:28 p.m.

2 stops11h 18m

C$ 553

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Wed 7/5

8:05 a.m.-7:30 p.m.

2 stops13h 55m

Chicago O'Hare Intl

Mon 12/5

4:00 p.m.-12:51 a.m.

1 stop6h 21m

C$ 610

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 12/5

2:00 p.m.-8:12 p.m.

1 stop8h 42m

Chicago O'Hare Intl

Wed 21/5

6:19 p.m.-1:02 p.m.

2 stops16h 13m

C$ 627

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 12/5

5:45 a.m.-9:52 a.m.

1 stop6h 37m

Chicago O'Hare Intl

Wed 21/5

6:11 p.m.-1:02 p.m.

1 stop16h 21m

C$ 633

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 30/4

1:05 p.m.-8:45 a.m.

2 stops22h 10m

Chicago Midway

Wed 7/5

9:40 a.m.-10:55 p.m.

1 stop10h 45m

C$ 636

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 26/4

1:05 p.m.-7:35 a.m.

2 stops21h 00m

Chicago O'Hare Intl

Mon 28/4

7:00 a.m.-2:17 a.m.

2 stops16h 47m

C$ 705

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Wed 7/5

5:25 a.m.-12:03 p.m.

1 stop9h 08m

Chicago O'Hare Intl

Mon 12/5

4:00 p.m.-12:51 a.m.

1 stop6h 21m

C$ 715

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 30/4

3:00 p.m.-7:42 a.m.

2 stops19h 12m

Chicago O'Hare Intl

Wed 7/5

11:03 a.m.-10:55 p.m.

2 stops9h 22m

C$ 788

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 1/5

6:10 p.m.-8:02 a.m.

1 stop16h 22m

C$ 386

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 1/5

1:10 p.m.-11:32 p.m.

2 stops12h 52m

C$ 449

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 12 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

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 2 April 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 2 April 2025.
Delta
8.0
Very good
7,897 reviews
Check prices

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
278 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,616 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,022 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 most popular routes from Newfoundland and Labrador to Chicago?

    While some choose either St John's - Chicago Midway or Deer Lake - Chicago O'Hare Intl, St John's - Chicago O'Hare Intl 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 2 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 659AverageC$ 788FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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?

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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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