Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Newfoundland and Labrador to Chicago from C$ 463

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 5/9. 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.
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
C$ 696Porter Airlines
Thu, 10 Sep - Thu, 17 Sep
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
7h 05m2 stops Toronto Island Ottawa
C$ 726Porter Airlines
Fri, 18 Sep - Mon, 21 Sep
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 a.m. - 10:55 p.m.MDW  Chicago Midway-YYT St John's
32h 40m2 stops Toronto Island Montreal St Hubert
C$ 749Porter Airlines
Fri, 18 Sep - Sun, 20 Sep
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
C$ 800Porter Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
C$ 809Porter Airlines
Thu, 24 Sep - Sun, 27 Sep
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
3:20 p.m. - 10:55 p.m.MDW  Chicago Midway-YYT St John's
29h 05m2 stops Toronto Island Montreal St Hubert
C$ 828Porter Airlines
Thu, 24 Sep - Sun, 27 Sep
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
11:45 a.m. - 10:55 p.m.MDW  Chicago Midway-YYT St John's
32h 40m2 stops Toronto Island Montreal St Hubert
C$ 842Porter Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
4:00 p.m. - 11:00 a.m.YYT  St John's-MDW Chicago Midway
21h 30m3 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl Toronto Island
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
C$ 894Porter Airlines
Thu, 10 Sep - Thu, 17 Sep
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
C$ 935Porter Airlines
Fri, 4 Sep - Mon, 7 Sep
Multiple Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Multiple Airlines Logo
11:45 a.m. - 11:35 p.m.MDW  Chicago Midway-YYT St John's
9h 20m1 stop Toronto Island
C$ 1,026Multiple Airlines
Fri, 4 Sep - Mon, 7 Sep

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
10 Sep
YYT6:00 a.m.St John's
11h 05m
2 stops
MDW2:35 p.m.Chicago Midway
17 Sep
MDW11:45 a.m.Chicago Midway
10h 40m
2 stops
YYT12:55 a.m.St John's
C$ 696
Porter Airlines
18 Sep
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
21 Sep
MDW3:20 p.m.Chicago Midway
7h 05m
2 stops
YYT12:55 a.m.St John's
C$ 726
Porter Airlines
18 Sep
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
20 Sep
MDW11:45 a.m.Chicago Midway
32h 40m
2 stops
YYT10:55 p.m.St John's
C$ 749

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 14 August 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 St John's - MDW Chicago Midway

YYTMDW

St John's

Thu 10/9

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

2 stops11h 05m

Chicago Midway

Thu 17/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

C$ 696
Quickest round-trip

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Fri 18/9

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

2 stops11h 00m

Chicago Midway

Mon 21/9

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

2 stops7h 05m

C$ 726

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Fri 18/9

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

2 stops11h 00m

Chicago Midway

Sun 20/9

11:45 a.m.-10:55 p.m.

2 stops32h 40m

C$ 749

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Tue 22/9

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

2 stops11h 05m

Chicago Midway

Sat 26/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

C$ 800

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Thu 24/9

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

2 stops11h 05m

Chicago Midway

Sun 27/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

C$ 809

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Thu 24/9

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

2 stops11h 05m

Chicago Midway

Sun 27/9

3:20 p.m.-10:55 p.m.

2 stops29h 05m

C$ 828

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Tue 22/9

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

2 stops11h 05m

Chicago Midway

Sat 26/9

11:45 a.m.-10:55 p.m.

2 stops32h 40m

C$ 842

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Thu 10/9

4:00 p.m.-11:00 a.m.

3 stops21h 30m

Chicago Midway

Thu 17/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

C$ 894

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Fri 4/9

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

2 stops11h 00m

Chicago Midway

Mon 7/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

C$ 935

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Fri 4/9

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

2 stops11h 05m

Chicago Midway

Mon 7/9

11:45 a.m.-11:35 p.m.

1 stop9h 20m

C$ 1,026

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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

11h 05m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 11h 05m
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

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
Valparaiso
Portage

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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 13/9
Sun 20/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago