Cheap flights from Newfoundland and Labrador to Chicago from C$ 556
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 18/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
5 Dec — 12 Dec1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheap flight deals from Newfoundland and Labrador to Chicago
Enter your travel dates to find the best prices.
Cheapest
Best
Last-minute
One-way
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 5 November 2026.
Wed 2/126:00 a.m. -
2 stops14h 10m
Wed 9/1212:15 p.m. -
2 stops10h 13m
Deal found 3/11C$ 871
Tue 24/112:30 p.m. -
1 stop7h 41m
Sat 28/1111:45 a.m. -
2 stops9h 11m
Deal found 2/11C$ 908
Tue 24/115:15 a.m. -
1 stop8h 22m
Sat 28/113:40 p.m. -
1 stop6h 49m
Deal found 1/11C$ 938
Wed 2/126:00 a.m. -
2 stops14h 10m
Wed 9/126:20 p.m. -
3 stops17h 44m
Deal found 3/11C$ 975
Wed 2/122:30 p.m. -
1 stop25h 01m
Wed 9/129:42 a.m. -
2 stops11h 12m
Deal found 3/11C$ 977
Sun 13/122:30 p.m. -
1 stop7h 43m
Tue 19/18:45 p.m. -
2 stops25h 48m
Deal found 3/11C$ 996
Sun 13/125:15 a.m. -
1 stop8h 22m
Tue 19/17:05 a.m. -
1 stop7h 50m
Deal found 3/11C$ 1,019
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 5 November 2026.
Sat 20/27:00 a.m. -
2 stops10h 01m
Wed 24/212:20 p.m. -
2 stops10h 08m
Deal found 4/11C$ 903
Sat 20/25:15 a.m. -
1 stop8h 22m
Wed 24/24:30 p.m. -
1 stop6h 41m
Deal found 1/11C$ 945
Tue 24/112:30 p.m. -
1 stop7h 41m
Sat 28/1111:45 a.m. -
2 stops9h 11m
Deal found 2/11C$ 908
Last-minute flights from Newfoundland and Labrador to Chicago
Discover last-minute flight deals from Newfoundland and Labrador to Chicago. Data last updated 5 November 2026 and is based on user searches.
Tue 24/112:30 p.m. -
1 stop7h 41m
Sat 28/1111:45 a.m. -
2 stops9h 11m
Deal found 2/11C$ 908
Tue 24/115:15 a.m. -
1 stop8h 22m
Sat 28/113:40 p.m. -
1 stop6h 49m
Deal found 1/11C$ 938
Wed 2/126:00 a.m. -
2 stops14h 10m
Wed 9/1212:15 p.m. -
2 stops10h 13m
Deal found 3/11C$ 871
Wed 2/126:00 a.m. -
2 stops14h 10m
Wed 9/126:20 p.m. -
3 stops17h 44m
Deal found 3/11C$ 975
Wed 2/122:30 p.m. -
1 stop25h 01m
Wed 9/129:42 a.m. -
2 stops11h 12m
Deal found 3/11C$ 977
Sun 13/122:30 p.m. -
1 stop7h 43m
Tue 19/18:45 p.m. -
2 stops25h 48m
Deal found 3/11C$ 996
Sun 13/125:15 a.m. -
1 stop8h 22m
Tue 19/17:05 a.m. -
1 stop7h 50m
Deal found 3/11C$ 1,019
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 5 November 2026.
Fri 18/126:40 a.m. -
1 stop9h 03m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 2/11C$ 556
Fri 18/126:40 a.m. -
2 stops19h 51m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 2/11C$ 666
Fri 18/127:00 a.m. -
3 stops37h 10m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 2/11C$ 669
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 5 November 2026.
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 7,457,451 searches. Data last updated 5 November 2026.
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
Cheapest round-trip
Quickest round-trip
St. John'sChicago
YYT St John's - ORD Chicago O'Hare Intl
YYTORD
St John's
Fri 18/12
6:40 a.m.-1:13 p.m.
1 stop9h 03m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-2:30 a.m.
Nonstop0h 00m
C$ 556
St. John'sChicago
YYT St John's - ORD Chicago O'Hare Intl
YYTORD
St John's
Fri 18/12
6:40 a.m.-12:01 a.m.
2 stops19h 51m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-2:30 a.m.
Nonstop0h 00m
C$ 666
St. John'sChicago
YYT St John's - ORD Chicago O'Hare Intl
YYTORD
St John's
Sat 20/2
7:00 a.m.-2:31 p.m.
2 stops10h 01m
Chicago O'Hare Intl
Wed 24/2
12:20 p.m.-12:58 a.m.
2 stops10h 08m
C$ 903
St. John'sChicago
YYT St John's - ORD Chicago O'Hare Intl
YYTORD
St John's
Tue 24/11
2:30 p.m.-7:41 p.m.
1 stop7h 41m
Chicago O'Hare Intl
Sat 28/11
11:45 a.m.-11:26 p.m.
2 stops9h 11m
C$ 908
St. John'sChicago
YYT St John's - ORD Chicago O'Hare Intl
YYTORD
St John's
Sat 20/2
5:15 a.m.-11:07 a.m.
1 stop8h 22m
Chicago O'Hare Intl
Wed 24/2
4:30 p.m.-1:41 a.m.
1 stop6h 41m
C$ 945
Flights are sorted by cheapest round-trip flights first.
Deals found on 2/11
Sorted by cheapest first
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.
YYT-ORD
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
CANL-CHI
YYT-ORD
No data available for this route at this time. Please check back soon.
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?
A quick flight from Newfoundland and Labrador to Chicago can take about 10h 01m. Porter Airlines provides one of the quickest options available for as low as C$ 903. The distance between Newfoundland and Labrador and Chicago is about 2816 km.
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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 5 November 2026.
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
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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