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Cheap flights from Newfoundland and Labrador to Chicago from C$ 1,034

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Newfoundland and Labrador to Chicago departing on 14/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Newfoundland and Labrador to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:15 a.m. - 11:55 a.m.
YYT
-
MDW
8h 10m
2 stops
Porter Airlines Logo
11:05 a.m. - 11:20 p.m.
MDW
-
YYT
9h 45m
2 stops
C$ 1,034Porter Airlines
Sat, 14 Feb - Wed, 18 Feb
Porter Airlines Logo
4:15 p.m. - 3:20 p.m.
YYT
-
MDW
25h 35m
2 stops
Porter Airlines Logo
11:05 a.m. - 1:01 a.m.
MDW
-
YYT
11h 26m
2 stops
C$ 1,087Porter Airlines
Sat, 14 Feb - Wed, 18 Feb
Porter Airlines Logo
4:15 p.m. - 3:20 p.m.
YYT
-
MDW
25h 35m
2 stops
Porter Airlines Logo
11:05 a.m. - 11:20 p.m.
MDW
-
YYT
9h 45m
2 stops
C$ 1,146Porter Airlines
Sat, 14 Feb - Wed, 18 Feb
WestJet Logo
3:00 p.m. - 6:05 p.m.
YYT
-
MDW
29h 35m
2 stops
WestJet Logo
1:05 p.m. - 6:20 a.m.
MDW
-
YYT
14h 45m
2 stops
C$ 1,386WestJet
Thu, 2 Jul - Tue, 21 Jul

Porter Airlines flights from Newfoundland and Labrador to Chicago Midway Airport

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago Midway Airport flight tickets
Porter Airlines
14 Feb
YYT6:15 a.m.St John's
8h 10m
2 stops
MDW11:55 a.m.Chicago Midway
18 Feb
MDW11:05 a.m.Chicago Midway
9h 45m
2 stops
YYT11:20 p.m.St John's
C$ 1,034
Porter Airlines
14 Feb
YYT4:15 p.m.St John's
25h 35m
2 stops
MDW3:20 p.m.Chicago Midway
18 Feb
MDW11:05 a.m.Chicago Midway
11h 26m
2 stops
YYT1:01 a.m.St John's
C$ 1,087
Porter Airlines
14 Feb
YYT4:15 p.m.St John's
25h 35m
2 stops
MDW3:20 p.m.Chicago Midway
18 Feb
MDW11:05 a.m.Chicago Midway
9h 45m
2 stops
YYT11:20 p.m.St John's
C$ 1,146

momondo Fare Finder

 
Customize your flight search to find flights from Newfoundland and Labrador to Chicago Midway Airport 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, momondo users made 96,600 searches. Data last updated 4 February 2026.
Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 14/2

6:15 a.m.-11:55 a.m.

2 stops8h 10m

Chicago Midway

Wed 18/2

11:05 a.m.-11:20 p.m.

2 stops9h 45m

C$ 1,034

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 14/2

4:15 p.m.-3:20 p.m.

2 stops25h 35m

Chicago Midway

Wed 18/2

11:05 a.m.-1:01 a.m.

2 stops11h 26m

C$ 1,087

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 14/2

4:15 p.m.-3:20 p.m.

2 stops25h 35m

Chicago Midway

Wed 18/2

11:05 a.m.-11:20 p.m.

2 stops9h 45m

C$ 1,146

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 2/7

3:00 p.m.-6:05 p.m.

2 stops29h 35m

Chicago Midway

Tue 21/7

1:05 p.m.-6:20 a.m.

2 stops14h 45m

C$ 1,386

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Newfoundland and Labrador to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

How long does it take to fly to Chicago Midway Airport?

Flight times from Newfoundland and Labrador to Chicago Midway Airport vary, but if you’re flying out of Deer Lake and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 6h 49m on average. Another popular route from Newfoundland and Labrador to Chicago Midway Airport is flying from St. John's to Chicago O'Hare Intl Airport, which will take roughly 7h 16m. Keep in mind that layovers or delays could extend your travel time.

Cheap Newfoundland and Labrador to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Newfoundland and Labrador to Chicago Midway Airport

Fastest flight time

25h 35m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 25h 35m
There are no direct flights from Newfoundland and Labrador to Chicago Midway Airport. There are no popular flight routes from Newfoundland and Labrador to Chicago Midway Airport.
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  • When did momondo last update prices for flights from Newfoundland and Labrador to Chicago Midway Airport?

    Prices for flights from Newfoundland and Labrador to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Newfoundland and Labrador to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Newfoundland and Labrador to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Newfoundland and Labrador to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Newfoundland and Labrador to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Newfoundland and Labrador to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Newfoundland and Labrador which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Newfoundland and Labrador to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Newfoundland and Labrador to Chicago.

I’m not ready to book a flight from Newfoundland and Labrador to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Newfoundland and Labrador and alert you when they change.

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