Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Newfoundland and Labrador to Chicago from C$ 339

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 25/9. 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

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

Find the cheapest flights from Newfoundland and Labrador to Chicago

Cheap round-trip flights

Porter Airlines Logo
7:00 a.m. - 4:24 p.m.YYT-MDW
11h 54m3 stops
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
C$ 652Porter Airlines
Find Deal
Thu, 25 Sep - Thu, 2 Oct
Porter Airlines Logo
7:00 a.m. - 4:24 p.m.YYT-MDW
11h 54m3 stops
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
C$ 679Porter Airlines
Find Deal
Thu, 11 Sep - Thu, 18 Sep
Porter Airlines Logo
1:15 p.m. - 8:39 a.m.YYT-MDW
21h 54m2 stops
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
C$ 814Porter Airlines
Find Deal
Thu, 25 Sep - Thu, 2 Oct
Porter Airlines Logo
1:15 p.m. - 8:39 a.m.YYT-MDW
21h 54m2 stops
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
C$ 871Porter Airlines
Find Deal
Fri, 12 Sep - Fri, 26 Sep
Porter Airlines Logo
7:00 a.m. - 4:24 p.m.YYT-MDW
11h 54m3 stops
Porter Airlines Logo
5:20 p.m. - 4:58 p.m.MDW-YYT
21h 08m3 stops
C$ 916Porter Airlines
Find Deal
Thu, 25 Sep - Thu, 2 Oct
Porter Airlines Logo
2:55 p.m. - 8:39 a.m.YYT-MDW
20h 14m2 stops
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
C$ 1,400Porter Airlines
Find Deal
Thu, 11 Sep - Thu, 18 Sep

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
25 Sep
YYT7:00 a.m.St John's
11h 54m
3 stops
MDW4:24 p.m.Chicago Midway
2 Oct
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
C$ 652
Find similar
Porter Airlines
11 Sep
YYT7:00 a.m.St John's
11h 54m
3 stops
MDW4:24 p.m.Chicago Midway
18 Sep
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
C$ 679
Find similar
Porter Airlines
25 Sep
YYT1:15 p.m.St John's
21h 54m
2 stops
MDW8:39 a.m.Chicago Midway
2 Oct
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
C$ 814
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 12 August 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

Thu 25/9

7:00 a.m.-4:24 p.m.

3 stops11h 54m

Chicago Midway

Thu 2/10

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 652

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 11/9

7:00 a.m.-4:24 p.m.

3 stops11h 54m

Chicago Midway

Thu 18/9

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 679

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 25/9

1:15 p.m.-8:39 a.m.

2 stops21h 54m

Chicago Midway

Thu 2/10

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 814

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 12/9

1:15 p.m.-8:39 a.m.

2 stops21h 54m

Chicago Midway

Fri 26/9

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 871

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 25/9

7:00 a.m.-4:24 p.m.

3 stops11h 54m

Chicago Midway

Thu 2/10

5:20 p.m.-4:58 p.m.

3 stops21h 08m

C$ 916

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 11/9

2:55 p.m.-8:39 a.m.

2 stops20h 14m

Chicago Midway

Thu 18/9

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 1,400

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 25/9

7:00 a.m.-4:24 p.m.

3 stops11h 54m

C$ 339

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 25/9

3:00 p.m.-9:51 a.m.

2 stops45h 21m

C$ 368

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 30/8

7:40 p.m.-5:37 p.m.

2 stops24h 27m

C$ 743

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 and WestJet are the most popular carriers 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

Best price found

C$ 339

Fastest flight time

11h 54m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Newfoundland and Labrador in the past 72 hours is C$ 339. The best round-trip flight deal from Newfoundland and Labrador to Chicago Midway Airport found on momondo in the last 72 hours is C$ 652.
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 11h 54m
There are no direct flights from Newfoundland and Labrador to Chicago Midway Airport. Popular non-direct route for this connection is St John's Airport - 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
Hammond
Munster
Benton Harbor
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.

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 17/8
Sun 24/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago