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Cheap flights from Newfoundland and Labrador to Chicago from C$ 402

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 7/7. 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

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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
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:55 a.m.
MDW
-
YYT
7h 05m
2 stops
C$ 694Porter Airlines
Wed, 29 Jul - Wed, 5 Aug
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:56 a.m.
MDW
-
YYT
7h 06m
2 stops
C$ 726Porter Airlines
Tue, 26 May - Fri, 29 May
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:56 a.m.
MDW
-
YYT
7h 06m
2 stops
C$ 727Porter Airlines
Tue, 26 May - Fri, 29 May
Porter Airlines Logo
6:00 a.m. - 12:10 p.m.
YYT
-
MDW
8h 40m
2 stops
Porter Airlines Logo
11:00 a.m. - 11:05 p.m.
MDW
-
YYT
9h 35m
2 stops
C$ 752Porter Airlines
Sat, 18 Apr - Wed, 22 Apr
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:25 a.m. - 12:56 a.m.
MDW
-
YYT
12h 01m
2 stops
C$ 757Porter Airlines
Tue, 26 May - Fri, 29 May
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:56 a.m.
MDW
-
YYT
7h 06m
2 stops
C$ 912Porter Airlines
Fri, 22 May - Mon, 1 Jun
Porter Airlines Logo
4:00 p.m. - 9:40 a.m.
YYT
-
MDW
20h 10m
3 stops
Porter Airlines Logo
3:20 p.m. - 12:55 a.m.
MDW
-
YYT
7h 05m
2 stops
C$ 1,104Porter Airlines
Wed, 29 Jul - Wed, 5 Aug
Multiple Airlines Logo
4:00 p.m. - 9:40 a.m.
YYT
-
MDW
20h 10m
3 stops
Multiple Airlines Logo
1:00 p.m. - 12:55 a.m.
MDW
-
YYT
9h 25m
3 stops
C$ 1,383Multiple Airlines
Wed, 29 Jul - Wed, 5 Aug

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
29 Jul
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
5 Aug
MDW3:20 p.m.Chicago Midway
7h 05m
2 stops
YYT12:55 a.m.St John's
C$ 694
Porter Airlines
26 May
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
29 May
MDW3:20 p.m.Chicago Midway
7h 06m
2 stops
YYT12:56 a.m.St John's
C$ 726
Porter Airlines
26 May
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
29 May
MDW3:20 p.m.Chicago Midway
7h 06m
2 stops
YYT12:56 a.m.St John's
C$ 727

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 22 March 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
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 29/7

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

2 stops11h 00m

Chicago Midway

Wed 5/8

3:20 p.m.-12:55 a.m.

2 stops7h 05m

C$ 694

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

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

2 stops11h 00m

Chicago Midway

Fri 29/5

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 726

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

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

2 stops11h 00m

Chicago Midway

Fri 29/5

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 727

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 18/4

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

2 stops8h 40m

Chicago Midway

Wed 22/4

11:00 a.m.-11:05 p.m.

2 stops9h 35m

C$ 752

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

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

2 stops11h 00m

Chicago Midway

Fri 29/5

10:25 a.m.-12:56 a.m.

2 stops12h 01m

C$ 757

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 22/5

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

2 stops11h 00m

Chicago Midway

Mon 1/6

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 912

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 29/7

4:00 p.m.-9:40 a.m.

3 stops20h 10m

Chicago Midway

Wed 5/8

3:20 p.m.-12:55 a.m.

2 stops7h 05m

C$ 1,104

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 29/7

4:00 p.m.-9:40 a.m.

3 stops20h 10m

Chicago Midway

Wed 5/8

1:00 p.m.-12:55 a.m.

3 stops9h 25m

C$ 1,383
Cheapest one-way
Quickest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 7/7

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

2 stops11h 00m

C$ 402

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 7/7

6:05 a.m.-6:31 p.m.

3 stops14h 56m

C$ 615

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

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

8h 40m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 8h 40m
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.
Search flight deals

  • 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
Munster
Hammond

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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