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Cheap flights from Newfoundland and Labrador to Chicago from C$ 272

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
27 Apr — 4 May1
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 22 April 2025.

Round-trip from

C$ 536

One-way from

C$ 272
Air Canada
  • Air Canada
  • 27/7-3/8
  • 2 total stops
  • 13h 00m total
  • Newfoundland and Labrador to Chicago
Search Deals
Air Canada
  • Air Canada
  • 5/6
  • 1 total stop
  • 6h 37m total
  • Newfoundland and Labrador to Chicago
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 22 April 2025.

Sun 27/75:50 a.m.YYT - ORD
1 stop6h 32mAir Canada
Sun 3/83:35 p.m.ORD - YYT
1 stop6h 28mAir Canada
Deal found 21/4C$ 536
Sun 27/75:50 a.m.YYT - ORD
1 stop6h 32mMultiple Airlines
Sun 3/810:00 a.m.ORD - YYT
2 stops12h 03mMultiple Airlines
Deal found 21/4C$ 586
Sat 28/68:45 a.m.YYT - ORD
2 stops17h 15mUnited Airlines
Wed 2/79:14 p.m.ORD - YYT
1 stop13h 02mUnited Airlines
Deal found 21/4C$ 656
Wed 7/56:00 a.m.YDF - ORD
1 stop6h 22mAir Canada
Mon 12/53:50 p.m.ORD - YDF
1 stop6h 31mAir Canada
Deal found 21/4C$ 703
Fri 9/52:55 p.m.YYT - MDW
2 stops20h 20mPorter Airlines
Fri 16/59:40 a.m.MDW - YYT
2 stops12h 18mPorter Airlines
Deal found 21/4C$ 939
Fri 25/41:05 p.m.YYT - MDW
3 stops30h 44mMultiple Airlines
Mon 28/45:35 p.m.MDW - YYT
2 stops27h 45mMultiple Airlines
Deal found 21/4C$ 1,705

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 22 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 - ORD

YYTORD

St John's

Sun 27/7

5:50 a.m.-9:52 a.m.

1 stop6h 32m

Chicago O'Hare Intl

Sun 3/8

3:35 p.m.-12:33 a.m.

1 stop6h 28m

C$ 536

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 27/7

5:50 a.m.-9:52 a.m.

1 stop6h 32m

Chicago O'Hare Intl

Sun 3/8

10:00 a.m.-12:33 a.m.

2 stops12h 03m

C$ 586

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 28/6

8:45 a.m.-11:30 p.m.

2 stops17h 15m

Chicago O'Hare Intl

Wed 2/7

9:14 p.m.-12:46 p.m.

1 stop13h 02m

C$ 656

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Wed 7/5

6:00 a.m.-9:52 a.m.

1 stop6h 22m

Chicago O'Hare Intl

Mon 12/5

3:50 p.m.-12:51 a.m.

1 stop6h 31m

C$ 703

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 9/5

2:55 p.m.-8:45 a.m.

2 stops20h 20m

Chicago Midway

Fri 16/5

9:40 a.m.-12:28 a.m.

2 stops12h 18m

C$ 939

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 5/6

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

1 stop6h 37m

C$ 272

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 5/6

6:00 a.m.-12:10 a.m.

2 stops20h 40m

C$ 300

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 5/6

3:00 p.m.-8:45 a.m.

3 stops20h 15m

C$ 300

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 25/9

5:50 a.m.-9:16 p.m.

2 stops17h 56m

C$ 334

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/4

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 22 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 22 April 2025.
Porter Airlines
8.0
Very good
284 reviews
Check prices

Comfort

8.1

Overall

8.0

Food

7.6

Crew

8.8

Boarding

8.2

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
284 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Comfort

8.1

Overall

8.0

Food

7.6

Crew

8.8

Boarding

8.2

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,684 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Comfort

8.1

Overall

8.0

Food

7.6

Crew

8.8

Boarding

8.2

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,170 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Comfort

8.1

Overall

8.0

Food

7.6

Crew

8.8

Boarding

8.2

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 Air Canada, which is currently one of the cheapest options available, starting at C$ 272. Porter Airlines flights start at C$ 300 while deals on United Airlines start at C$ 334 one-way.

  • 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 22 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 634AverageC$ 758FlexibilityNo 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?

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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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