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Cheap flights from Newfoundland and Labrador to Chicago from C$ 390

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 24/1. 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
6:00 a.m. - 3:20 p.m.
YYT
-
MDW
11h 50m2 stops
Porter Airlines Logo
12:45 p.m. - 11:05 p.m.
MDW
-
YYT
7h 50m2 stops
C$ 730Porter Airlines
Wed, 15 Apr - Sat, 18 Apr
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.
YYT
-
MDW
29h 44m2 stops
Porter Airlines Logo
9:40 a.m. - 12:28 a.m.
MDW
-
YYT
12h 18m2 stops
C$ 903Porter Airlines
Sat, 30 May - Wed, 3 Jun
Porter Airlines Logo
6:00 a.m. - 10:05 a.m.
YYT
-
MDW
30h 35m2 stops
Porter Airlines Logo
12:45 p.m. - 11:15 p.m.
MDW
-
YYT
8h 00m2 stops
C$ 1,168Porter Airlines
Sat, 24 Jan - Sat, 31 Jan

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
15 Apr
YYT6:00 a.m.St John's
11h 50m
2 stops
MDW3:20 p.m.Chicago Midway
18 Apr
MDW12:45 p.m.Chicago Midway
7h 50m
2 stops
YYT11:05 p.m.St John's
C$ 730
Find similar
Porter Airlines
30 May
YYT1:10 p.m.St John's
29h 44m
2 stops
MDW4:24 p.m.Chicago Midway
3 Jun
MDW9:40 a.m.Chicago Midway
12h 18m
2 stops
YYT12:28 a.m.St John's
C$ 903
Find similar
Porter Airlines
24 Jan
YYT6:00 a.m.St John's
30h 35m
2 stops
MDW10:05 a.m.Chicago Midway
31 Jan
MDW12:45 p.m.Chicago Midway
8h 00m
2 stops
YYT11:15 p.m.St John's
C$ 1,168
Find similar

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 11 December 2025.
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

Wed 15/4

6:00 a.m.-3:20 p.m.

2 stops11h 50m

Chicago Midway

Sat 18/4

12:45 p.m.-11:05 p.m.

2 stops7h 50m

C$ 730

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 30/5

1:10 p.m.-4:24 p.m.

2 stops29h 44m

Chicago Midway

Wed 3/6

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

2 stops12h 18m

C$ 903

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 24/1

6:00 a.m.-10:05 a.m.

2 stops30h 35m

Chicago Midway

Sat 31/1

12:45 p.m.-11:15 p.m.

2 stops8h 00m

C$ 1,168

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 24/1

6:20 a.m.-11:45 a.m.

3 stops31h 55m

C$ 390

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 24/1

6:20 a.m.-11:50 a.m.

2 stops8h 00m

C$ 538

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

7h 50m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 7h 50m
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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