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Cheap flights from Newfoundland and Labrador to Chicago from $267

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 6/30. 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.
Multiple Airlines Logo
1:20 pm - 9:40 am
YYT
-
MDW
22h 50m
1 stop
Multiple Airlines Logo
10:25 am - 10:55 pm
MDW
-
YYT
34h 00m
2 stops
$513Multiple Airlines
Wed, Jun 24 - Wed, Jul 1
Porter Airlines Logo
1:45 pm - 9:40 am
YYT
-
MDW
22h 25m
2 stops
Porter Airlines Logo
10:25 am - 12:55 am
MDW
-
YYT
12h 00m
2 stops
$575Porter Airlines
Wed, Jun 24 - Wed, Jul 1
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:20 am - 12:55 am
MDW
-
YYT
12h 05m
2 stops
$579Porter Airlines
Wed, Aug 19 - Sat, Aug 22
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:20 am - 12:55 am
MDW
-
YYT
12h 05m
2 stops
$580Porter Airlines
Wed, Aug 19 - Sat, Aug 22
Porter Airlines Logo
4:00 pm - 9:40 am
YYT
-
MDW
20h 10m
3 stops
Porter Airlines Logo
10:25 am - 12:55 am
MDW
-
YYT
12h 00m
2 stops
$584Porter Airlines
Wed, Jun 24 - Wed, Jul 1
Multiple Airlines Logo
1:20 pm - 9:40 am
YYT
-
MDW
22h 50m
1 stop
Multiple Airlines Logo
10:25 am - 12:38 am
MDW
-
YYT
11h 43m
1 stop
$586Multiple Airlines
Wed, Jun 24 - Wed, Jul 1
Porter Airlines Logo
6:00 am - 2:35 pm
YYT
-
MDW
11h 05m
2 stops
Porter Airlines Logo
10:20 am - 10:55 pm
MDW
-
YYT
10h 05m
2 stops
$599Porter Airlines
Wed, Aug 19 - Sat, Aug 22
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:25 am - 12:56 am
MDW
-
YYT
12h 01m
2 stops
$633Porter Airlines
Sun, Jun 14 - Sun, Jun 21
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:20 am - 10:55 pm
MDW
-
YYT
10h 05m
2 stops
$668Porter Airlines
Wed, Aug 19 - Sat, Aug 22

Porter Airlines flights from Newfoundland and Labrador to Chicago

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago flight tickets
Porter Airlines
Jun 24
YYT1:45 pmSt John's
22h 25m
2 stops
MDW9:40 amChicago Midway
Jul 1
MDW10:25 amChicago Midway
12h 00m
2 stops
YYT12:55 amSt John's
$575
Porter Airlines
Aug 19
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Aug 22
MDW10:20 amChicago Midway
12h 05m
2 stops
YYT12:55 amSt John's
$579
Porter Airlines
Aug 19
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Aug 22
MDW10:20 amChicago Midway
12h 05m
2 stops
YYT12:55 amSt John's
$580

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 May 29, 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

Cheapest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 6/24

1:20 pm-9:40 am

1 stop22h 50m

Chicago Midway

Wed 7/1

10:25 am-10:55 pm

2 stops34h 00m

$513

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 6/24

1:45 pm-9:40 am

2 stops22h 25m

Chicago Midway

Wed 7/1

10:25 am-12:55 am

2 stops12h 00m

$575

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 8/19

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sat 8/22

10:20 am-12:55 am

2 stops12h 05m

$579

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 8/19

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sat 8/22

10:20 am-12:55 am

2 stops12h 05m

$580

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 6/24

4:00 pm-9:40 am

3 stops20h 10m

Chicago Midway

Wed 7/1

10:25 am-12:55 am

2 stops12h 00m

$584

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 6/24

1:20 pm-9:40 am

1 stop22h 50m

Chicago Midway

Wed 7/1

10:25 am-12:38 am

1 stop11h 43m

$586

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 8/19

6:00 am-2:35 pm

2 stops11h 05m

Chicago Midway

Sat 8/22

10:20 am-10:55 pm

2 stops10h 05m

$599

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 6/14

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sun 6/21

10:25 am-12:56 am

2 stops12h 01m

$633
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 8/19

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sat 8/22

10:20 am-10:55 pm

2 stops10h 05m

$668
Cheapest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 6/30

6:00 am-9:40 am

2 stops30h 10m

$267

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 and WestJet are the most popular carriers 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

Fastest flight time

11h 00m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago takes 11h 00m
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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Frequently asked questions about flying from Newfoundland and Labrador to Chicago

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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