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Cheap flights from Newfoundland and Labrador to Chicago from $452

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 4/23. 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

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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.
Multiple Airlines Logo
6:20 am - 10:05 am
YYT
-
MDW
30h 15m
2 stops
Multiple Airlines Logo
11:00 am - 10:55 pm
MDW
-
YYT
9h 25m
1 stop
$452Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
6:20 am - 3:20 pm
YYT
-
MDW
11h 30m
2 stops
Multiple Airlines Logo
4:15 pm - 10:55 pm
MDW
-
YYT
28h 10m
1 stop
$482Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
6:20 am - 3:20 pm
YYT
-
MDW
11h 30m
2 stops
Multiple Airlines Logo
11:00 am - 10:55 pm
MDW
-
YYT
9h 25m
1 stop
$485Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
5:40 pm - 11:50 am
YYT
-
MDW
20h 40m
1 stop
Multiple Airlines Logo
11:00 am - 10:55 pm
MDW
-
YYT
9h 25m
1 stop
$512Multiple Airlines
Fri, Apr 24 - Sun, Apr 26
Porter Airlines Logo
6:20 am - 3:20 pm
YYT
-
MDW
11h 30m
2 stops
Porter Airlines Logo
11:00 am - 1:01 am
MDW
-
YYT
11h 31m
2 stops
$526Porter Airlines
Thu, Apr 23 - Sun, Apr 26
Porter Airlines Logo
6:00 am - 3:20 pm
YYT
-
MDW
11h 50m
2 stops
Porter Airlines Logo
11:00 am - 11:05 pm
MDW
-
YYT
9h 35m
2 stops
$537Porter Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
5:40 pm - 11:50 am
YYT
-
MDW
20h 40m
1 stop
Multiple Airlines Logo
11:00 am - 10:55 pm
MDW
-
YYT
9h 25m
1 stop
$542Multiple Airlines
Fri, Apr 24 - Tue, Apr 28
Porter Airlines Logo
6:15 am - 11:55 am
YYT
-
MDW
8h 10m
2 stops
Porter Airlines Logo
11:05 am - 11:20 pm
MDW
-
YYT
9h 45m
2 stops
$691Porter Airlines
Sat, Feb 14 - Wed, Feb 18
Porter Airlines Logo
6:15 am - 11:55 am
YYT
-
MDW
8h 10m
2 stops
Porter Airlines Logo
11:05 am - 11:20 pm
MDW
-
YYT
9h 45m
2 stops
$757Porter Airlines
Sat, Feb 14 - Wed, Feb 18
Porter Airlines Logo
4:15 pm - 3:20 pm
YYT
-
MDW
25h 35m
2 stops
Porter Airlines Logo
11:05 am - 1:01 am
MDW
-
YYT
11h 26m
2 stops
$796Porter Airlines
Sat, Feb 14 - Wed, Feb 18

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 23
YYT6:20 amSt John's
11h 30m
2 stops
MDW3:20 pmChicago Midway
Apr 26
MDW11:00 amChicago Midway
11h 31m
2 stops
YYT1:01 amSt John's
$526
Porter Airlines
Apr 23
YYT6:00 amSt John's
11h 50m
2 stops
MDW3:20 pmChicago Midway
Apr 27
MDW11:00 amChicago Midway
9h 35m
2 stops
YYT11:05 pmSt John's
$537
Porter Airlines
Feb 14
YYT6:15 amSt John's
8h 10m
2 stops
MDW11:55 amChicago Midway
Feb 18
MDW11:05 amChicago Midway
9h 45m
2 stops
YYT11:20 pmSt John's
$691

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 February 3, 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

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/23

6:20 am-10:05 am

2 stops30h 15m

Chicago Midway

Mon 4/27

11:00 am-10:55 pm

1 stop9h 25m

$452

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/23

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Tue 4/28

4:15 pm-10:55 pm

1 stop28h 10m

$482

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 4/24

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Mon 4/27

11:00 am-10:55 pm

1 stop9h 25m

$485

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 4/24

5:40 pm-11:50 am

1 stop20h 40m

Chicago Midway

Sun 4/26

11:00 am-10:55 pm

1 stop9h 25m

$512

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/23

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Sun 4/26

11:00 am-1:01 am

2 stops11h 31m

$526

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/23

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Mon 4/27

11:00 am-11:05 pm

2 stops9h 35m

$537

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 4/24

5:40 pm-11:50 am

1 stop20h 40m

Chicago Midway

Tue 4/28

11:00 am-10:55 pm

1 stop9h 25m

$542

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 2/14

6:15 am-11:55 am

2 stops8h 10m

Chicago Midway

Wed 2/18

11:05 am-11:20 pm

2 stops9h 45m

$691

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 2/14

6:15 am-11:55 am

2 stops8h 10m

Chicago Midway

Wed 2/18

11:05 am-11:20 pm

2 stops9h 45m

$757

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 2/14

4:15 pm-3:20 pm

2 stops25h 35m

Chicago Midway

Wed 2/18

11:05 am-1:01 am

2 stops11h 26m

$796

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

25h 35m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago Midway Airport takes 25h 35m
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 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.

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

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Newfoundland and Labrador from Chicago Midway Airport. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

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

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
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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?

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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