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Cheap flights from Newfoundland and Labrador to Chicago from $283

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 1/24. 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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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
6:00 am - 3:20 pm
YYT
-
MDW
11h 50m2 stops
Porter Airlines Logo
12:45 pm - 11:05 pm
MDW
-
YYT
7h 50m2 stops
$529Porter Airlines
Wed, Apr 15 - Sat, Apr 18
Porter Airlines Logo
10:00 am - 3:20 pm
YYT
-
MDW
7h 50m2 stops
Porter Airlines Logo
11:00 am - 10:23 pm
MDW
-
YYT
8h 53m2 stops
$548Porter Airlines
Thu, Dec 25 - Wed, Dec 31
Porter Airlines Logo
1:10 pm - 4:24 pm
YYT
-
MDW
29h 44m2 stops
Porter Airlines Logo
9:40 am - 12:28 am
MDW
-
YYT
12h 18m2 stops
$655Porter Airlines
Sat, May 30 - Wed, Jun 3
Porter Airlines Logo
3:00 pm - 8:45 am
YYT
-
MDW
20h 15m2 stops
Porter Airlines Logo
9:40 am - 12:28 am
MDW
-
YYT
12h 18m2 stops
$656Porter Airlines
Sat, May 30 - Wed, Jun 3
Porter Airlines Logo
6:00 am - 10:05 am
YYT
-
MDW
30h 35m2 stops
Porter Airlines Logo
12:45 pm - 11:15 pm
MDW
-
YYT
8h 00m2 stops
$847Porter Airlines
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
5:00 am - 3:20 pm
YYT
-
MDW
12h 50m1 stop
Multiple Airlines Logo
11:00 am - 10:23 pm
MDW
-
YYT
8h 53m2 stops
$928Multiple Airlines
Thu, Dec 25 - Wed, Dec 31
Multiple Airlines Logo
5:00 am - 3:20 pm
YYT
-
MDW
12h 50m1 stop
Multiple Airlines Logo
11:00 am - 1:58 am
MDW
-
YYT
12h 28m1 stop
$1,052Multiple Airlines
Thu, Dec 25 - Wed, Dec 31

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
Apr 15
YYT6:00 amSt John's
11h 50m
2 stops
MDW3:20 pmChicago Midway
Apr 18
MDW12:45 pmChicago Midway
7h 50m
2 stops
YYT11:05 pmSt John's
$529
Find similar
Porter Airlines
Dec 25
YYT10:00 amSt John's
7h 50m
2 stops
MDW3:20 pmChicago Midway
Dec 31
MDW11:00 amChicago Midway
8h 53m
2 stops
YYT10:23 pmSt John's
$548
Find similar
Porter Airlines
May 30
YYT1:10 pmSt John's
29h 44m
2 stops
MDW4:24 pmChicago Midway
Jun 3
MDW9:40 amChicago Midway
12h 18m
2 stops
YYT12:28 amSt John's
$655
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 832,500 searches. Data last updated December 11, 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 4/15

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Sat 4/18

12:45 pm-11:05 pm

2 stops7h 50m

$529

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 12/25

10:00 am-3:20 pm

2 stops7h 50m

Chicago Midway

Wed 12/31

11:00 am-10:23 pm

2 stops8h 53m

$548

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 5/30

1:10 pm-4:24 pm

2 stops29h 44m

Chicago Midway

Wed 6/3

9:40 am-12:28 am

2 stops12h 18m

$655

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 5/30

3:00 pm-8:45 am

2 stops20h 15m

Chicago Midway

Wed 6/3

9:40 am-12:28 am

2 stops12h 18m

$656

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/24

6:00 am-10:05 am

2 stops30h 35m

Chicago Midway

Sat 1/31

12:45 pm-11:15 pm

2 stops8h 00m

$847

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 12/25

5:00 am-3:20 pm

1 stop12h 50m

Chicago Midway

Wed 12/31

11:00 am-10:23 pm

2 stops8h 53m

$928

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 12/25

5:00 am-3:20 pm

1 stop12h 50m

Chicago Midway

Wed 12/31

11:00 am-1:58 am

1 stop12h 28m

$1,052

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/24

6:20 am-11:45 am

3 stops31h 55m

$283

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/24

6:20 am-11:50 am

2 stops8h 00m

$390

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.
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 refresh daily.

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

    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 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.

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
Crown Point
Munster
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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Newfoundland and Labrador.

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 helps you find the best flight between Newfoundland and Labrador and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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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