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Cheap flights from Newfoundland and Labrador to Chicago from $313

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 10/28. 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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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 - 8:32 amYYT-MDW
28h 42m2 stops
Multiple Airlines Logo
11:00 am - 4:45 pmMDW-YYT
27h 15m1 stop
$425Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m2 stops
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
$460Porter Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
Porter Airlines Logo
5:40 pm - 11:50 amYYT-MDW
20h 40m1 stop
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
$468Porter Airlines
Find Deal
Fri, Oct 31 - Thu, Nov 6
Porter Airlines Logo
5:40 pm - 11:50 amYYT-MDW
20h 40m1 stop
Porter Airlines Logo
11:00 am - 4:45 pmMDW-YYT
27h 15m1 stop
$482Porter Airlines
Find Deal
Fri, Oct 31 - Thu, Nov 6
Porter Airlines Logo
6:20 am - 3:20 pmYYT-MDW
11h 30m2 stops
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
$483Porter Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m3 stops
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
$497Porter Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m3 stops
Porter Airlines Logo
11:00 am - 11:15 pmMDW-YYT
9h 45m3 stops
$516Porter Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m2 stops
Porter Airlines Logo
11:00 am - 11:15 pmMDW-YYT
9h 45m3 stops
$571Porter Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
Porter Airlines Logo
4:15 pm - 11:50 amYYT-MDW
22h 05m2 stops
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
$585Porter Airlines
Find Deal
Fri, Oct 31 - Thu, Nov 6
Multiple Airlines Logo
4:15 pm - 10:05 amYYT-MDW
20h 20m3 stops
Multiple Airlines Logo
11:00 am - 11:15 pmMDW-YYT
9h 45m3 stops
$1,074Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6

Porter Airlines flights from Newfoundland and Labrador to Chicago

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago flight tickets
Porter Airlines
Nov 14
YYT6:00 amSt John's
11h 50m
2 stops
MDW3:20 pmChicago Midway
Nov 21
MDW11:00 amChicago Midway
11h 31m
2 stops
YYT1:01 amSt John's
$460
Find similar
Porter Airlines
Oct 31
YYT5:40 pmSt John's
20h 40m
1 stop
MDW11:50 amChicago Midway
Nov 6
MDW11:00 amChicago Midway
11h 31m
2 stops
YYT1:01 amSt John's
$468
Find similar
Porter Airlines
Oct 31
YYT5:40 pmSt John's
20h 40m
1 stop
MDW11:50 amChicago Midway
Nov 6
MDW11:00 amChicago Midway
27h 15m
1 stop
YYT4:45 pmSt John's
$482
Find similar

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 October 2, 2025.
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 10/30

6:20 am-8:32 am

2 stops28h 42m

Chicago Midway

Thu 11/6

11:00 am-4:45 pm

1 stop27h 15m

$425

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 11/14

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Fri 11/21

11:00 am-1:01 am

2 stops11h 31m

$460

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 10/31

5:40 pm-11:50 am

1 stop20h 40m

Chicago Midway

Thu 11/6

11:00 am-1:01 am

2 stops11h 31m

$468

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 10/31

5:40 pm-11:50 am

1 stop20h 40m

Chicago Midway

Thu 11/6

11:00 am-4:45 pm

1 stop27h 15m

$482

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 10/30

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Thu 11/6

11:00 am-1:01 am

2 stops11h 31m

$483

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 10/30

6:00 am-3:20 pm

3 stops11h 50m

Chicago Midway

Thu 11/6

11:00 am-1:01 am

2 stops11h 31m

$497

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 10/30

6:00 am-3:20 pm

3 stops11h 50m

Chicago Midway

Thu 11/6

11:00 am-11:15 pm

3 stops9h 45m

$516

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 11/14

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Fri 11/21

11:00 am-11:15 pm

3 stops9h 45m

$571

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 10/31

4:15 pm-11:50 am

2 stops22h 05m

Chicago Midway

Thu 11/6

11:00 am-1:01 am

2 stops11h 31m

$585

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 10/30

4:15 pm-10:05 am

3 stops20h 20m

Chicago Midway

Thu 11/6

11:00 am-11:15 pm

3 stops9h 45m

$1,074

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Newfoundland and Labrador to Chicago

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?

Porter Airlines is the most popular carrier operating from Newfoundland and Labrador to Chicago

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

Direct flights

None
There are no direct flights from Newfoundland and Labrador to Chicago. There are no popular flight routes from Newfoundland and Labrador to Chicago.
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  • 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.

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
Lansing
Portage
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?

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.

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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