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Cheap flights from Newfoundland and Labrador to Chicago from C$ 367

This is the cheapest one-way 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 10/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Newfoundland and Labrador to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:00 p.m. - 9:40 a.m.
YYT
-
MDW
17h 10m
1 stop
Multiple Airlines Logo
3:15 p.m. - 10:55 p.m.
MDW
-
YYT
29h 10m
1 stop
C$ 928Multiple Airlines
Thu, 9 Jul - Mon, 24 Aug
Multiple Airlines Logo
6:00 a.m. - 2:35 p.m.
YYT
-
MDW
11h 05m
2 stops
Multiple Airlines Logo
3:15 p.m. - 10:55 p.m.
MDW
-
YYT
29h 10m
1 stop
C$ 939Multiple Airlines
Thu, 9 Jul - Mon, 24 Aug
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:15 p.m. - 12:55 a.m.
MDW
-
YYT
7h 10m
2 stops
C$ 942Porter Airlines
Thu, 9 Jul - Mon, 24 Aug
WestJet Logo
3:00 p.m. - 9:50 a.m.
YYT
-
MDW
21h 20m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,058WestJet
Tue, 15 Sep - Sun, 20 Sep
WestJet Logo
3:00 p.m. - 6:19 p.m.
YYT
-
MDW
29h 49m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,088WestJet
Wed, 16 Sep - Sun, 20 Sep
WestJet Logo
3:00 p.m. - 9:50 a.m.
YYT
-
MDW
21h 20m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,091WestJet
Tue, 15 Sep - Tue, 22 Sep
WestJet Logo
3:00 p.m. - 9:50 a.m.
YYT
-
MDW
21h 20m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,108WestJet
Tue, 15 Sep - Mon, 21 Sep
WestJet Logo
3:00 p.m. - 6:19 p.m.
YYT
-
MDW
29h 49m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,121WestJet
Wed, 16 Sep - Tue, 22 Sep
WestJet Logo
3:00 p.m. - 9:07 a.m.
YYT
-
MDW
20h 37m
2 stops
WestJet Logo
7:13 p.m. - 10:55 p.m.
MDW
-
YYT
49h 12m
2 stops
C$ 1,159WestJet
Wed, 16 Sep - Mon, 21 Sep
WestJet Logo
3:00 p.m. - 9:50 a.m.
YYT
-
MDW
21h 20m
2 stops
WestJet Logo
1:19 p.m. - 6:45 a.m.
MDW
-
YYT
14h 56m
2 stops
C$ 1,470WestJet
Thu, 17 Sep - Mon, 21 Sep

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WestJet flights from Newfoundland and Labrador to Chicago Midway Airport

Our best WestJet deals on Newfoundland and Labrador to Chicago Midway Airport flight tickets
WestJet
15 Sep
YYT3:00 p.m.St John's
21h 20m
2 stops
MDW9:50 a.m.Chicago Midway
20 Sep
MDW9:29 a.m.Chicago Midway
10h 56m
2 stops
YYT10:55 p.m.St John's
C$ 1,058
WestJet
16 Sep
YYT3:00 p.m.St John's
29h 49m
2 stops
MDW6:19 p.m.Chicago Midway
20 Sep
MDW9:29 a.m.Chicago Midway
10h 56m
2 stops
YYT10:55 p.m.St John's
C$ 1,088
WestJet
15 Sep
YYT3:00 p.m.St John's
21h 20m
2 stops
MDW9:50 a.m.Chicago Midway
22 Sep
MDW9:29 a.m.Chicago Midway
10h 56m
2 stops
YYT10:55 p.m.St John's
C$ 1,091

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 24 June 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

Cheapest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 9/7

7:00 p.m.-9:40 a.m.

1 stop17h 10m

Chicago Midway

Mon 24/8

3:15 p.m.-10:55 p.m.

1 stop29h 10m

C$ 928

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 9/7

6:00 a.m.-2:35 p.m.

2 stops11h 05m

Chicago Midway

Mon 24/8

3:15 p.m.-10:55 p.m.

1 stop29h 10m

C$ 939
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 9/7

6:05 a.m.-2:35 p.m.

2 stops11h 00m

Chicago Midway

Mon 24/8

3:15 p.m.-12:55 a.m.

2 stops7h 10m

C$ 942

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-9:50 a.m.

2 stops21h 20m

Chicago Midway

Sun 20/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,058

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 16/9

3:00 p.m.-6:19 p.m.

2 stops29h 49m

Chicago Midway

Sun 20/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,088

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-9:50 a.m.

2 stops21h 20m

Chicago Midway

Tue 22/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,091

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-9:50 a.m.

2 stops21h 20m

Chicago Midway

Mon 21/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,108

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 16/9

3:00 p.m.-6:19 p.m.

2 stops29h 49m

Chicago Midway

Tue 22/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,121

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 16/9

3:00 p.m.-9:07 a.m.

2 stops20h 37m

Chicago Midway

Mon 21/9

7:13 p.m.-10:55 p.m.

2 stops49h 12m

C$ 1,159

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 17/9

3:00 p.m.-9:50 a.m.

2 stops21h 20m

Chicago Midway

Mon 21/9

1:19 p.m.-6:45 a.m.

2 stops14h 56m

C$ 1,470

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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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

What is the cheapest airline that flies from Newfoundland and Labrador to Chicago Midway?

Porter Airlines is the most popular carrier operating from Newfoundland and Labrador to Chicago Midway

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

10h 15m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 10h 15m
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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Frequently asked questions about flying from Newfoundland and Labrador to Chicago Midway Airport

  • 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
Merrillville
Hammond
Munster

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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