Latest deals
FAQs
Price Alerts

Cheap flights from Newfoundland and Labrador to Chicago from $385

This is the cheapest round-trip 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 3/26. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:00 pm - 10:05 am
YYT
-
MDW
21h 35m
1 stop
Multiple Airlines Logo
11:00 am - 1:00 am
MDW
-
YYT
11h 30m
2 stops
$385Multiple Airlines
Thu, Mar 26 - Mon, Mar 30
Porter Airlines Logo
4:15 pm - 10:05 am
YYT
-
MDW
20h 20m
3 stops
Porter Airlines Logo
11:00 am - 1:00 am
MDW
-
YYT
11h 30m
2 stops
$513Porter Airlines
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
3:00 pm - 10:05 am
YYT
-
MDW
21h 35m
1 stop
Multiple Airlines Logo
11:00 am - 11:42 am
MDW
-
YYT
22h 12m
1 stop
$528Multiple Airlines
Thu, Mar 26 - Wed, Apr 1
Porter Airlines Logo
6:20 am - 10:05 am
YYT
-
MDW
30h 15m
2 stops
Porter Airlines Logo
11:00 am - 1:00 am
MDW
-
YYT
11h 30m
2 stops
$580Porter Airlines
Thu, Mar 26 - Mon, Mar 30
Porter Airlines Logo
4:15 pm - 10:05 am
YYT
-
MDW
20h 20m
2 stops
Porter Airlines Logo
11:00 am - 1:01 am
MDW
-
YYT
11h 31m
2 stops
$589Porter Airlines
Thu, Mar 26 - Wed, Apr 1
Porter Airlines Logo
4:15 pm - 10:05 am
YYT
-
MDW
20h 20m
2 stops
Porter Airlines Logo
11:00 am - 11:42 am
MDW
-
YYT
22h 12m
1 stop
$594Porter Airlines
Thu, Mar 26 - Wed, Apr 1
Multiple Airlines Logo
4:15 pm - 10:05 am
YYT
-
MDW
20h 20m
3 stops
Multiple Airlines Logo
1:10 pm - 1:00 am
MDW
-
YYT
33h 20m
3 stops
$625Multiple Airlines
Thu, Mar 26 - Mon, Mar 30

Porter Airlines flights from Newfoundland and Labrador to Chicago

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago flight tickets
Porter Airlines
Mar 26
YYT4:15 pmSt John's
20h 20m
3 stops
MDW10:05 amChicago Midway
Mar 30
MDW11:00 amChicago Midway
11h 30m
2 stops
YYT1:00 amSt John's
$513
Porter Airlines
Mar 26
YYT6:20 amSt John's
30h 15m
2 stops
MDW10:05 amChicago Midway
Mar 30
MDW11:00 amChicago Midway
11h 30m
2 stops
YYT1:00 amSt John's
$580
Porter Airlines
Mar 26
YYT4:15 pmSt John's
20h 20m
2 stops
MDW10:05 amChicago Midway
Apr 1
MDW11:00 amChicago Midway
11h 31m
2 stops
YYT1:01 amSt John's
$589

momondo Fare Finder

 
Customize your flight search to find flights from Newfoundland and Labrador to Chicago 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 832,500 searches. Data last updated February 27, 2026.
Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

3:00 pm-10:05 am

1 stop21h 35m

Chicago Midway

Mon 3/30

11:00 am-1:00 am

2 stops11h 30m

$385

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

4:15 pm-10:05 am

3 stops20h 20m

Chicago Midway

Mon 3/30

11:00 am-1:00 am

2 stops11h 30m

$513

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

3:00 pm-10:05 am

1 stop21h 35m

Chicago Midway

Wed 4/1

11:00 am-11:42 am

1 stop22h 12m

$528

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

6:20 am-10:05 am

2 stops30h 15m

Chicago Midway

Mon 3/30

11:00 am-1:00 am

2 stops11h 30m

$580

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

4:15 pm-10:05 am

2 stops20h 20m

Chicago Midway

Wed 4/1

11:00 am-1:01 am

2 stops11h 31m

$589

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

4:15 pm-10:05 am

2 stops20h 20m

Chicago Midway

Wed 4/1

11:00 am-11:42 am

1 stop22h 12m

$594

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 3/26

4:15 pm-10:05 am

3 stops20h 20m

Chicago Midway

Mon 3/30

1:10 pm-1:00 am

3 stops33h 20m

$625

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Cheap Newfoundland and Labrador to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Newfoundland and Labrador to Chicago

Fastest flight time

21h 35m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago takes 21h 35m
There are no direct flights from Newfoundland and Labrador to Chicago. There are no popular flight routes from Newfoundland and Labrador to Chicago.
Search flight deals

  • When did momondo last update prices for flights from Newfoundland and Labrador to Chicago?

    Prices for flights from Newfoundland and Labrador to Chicago were last updated today.

  • How old do you have to be to fly from Newfoundland and Labrador to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Newfoundland and Labrador to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • How do I get Price Alerts for flights from Newfoundland and Labrador to Chicago?

    Price Alerts will notify you by email when the price for flights to Chicago from Newfoundland and Labrador decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Newfoundland and Labrador to Chicago with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Newfoundland and Labrador to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Newfoundland and Labrador to Chicago for you.

Can I find flights from Newfoundland and Labrador to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Newfoundland and Labrador with this policy.

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?

Yes momondo offers price alerts on flights to Chicago from Newfoundland and Labrador. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago 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 3/29
Sun 4/5
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport