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Cheap flights from Newfoundland and Labrador to Chicago from $368

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 7/21. 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
1 adult, Economy, 0 bags

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
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:15 pm - 12:55 am
MDW
-
YYT
7h 10m
2 stops
$538Porter Airlines
Sun, Aug 23 - Sun, Aug 30
Porter Airlines Logo
4:00 pm - 9:45 am
YYT
-
MDW
20h 15m
3 stops
Porter Airlines Logo
10:20 am - 12:55 am
MDW
-
YYT
12h 05m
2 stops
$628Porter Airlines
Sun, Aug 23 - Sun, Aug 30
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
$714Porter Airlines
Sun, Aug 9 - Sun, Aug 16
Delta Logo
3:00 pm - 6:19 pm
YYT
-
MDW
29h 49m
2 stops
Delta Logo
7:01 pm - 10:55 pm
MDW
-
YYT
25h 24m
2 stops
$844Delta
Thu, Sep 10 - Mon, Sep 14
WestJet Logo
3:00 pm - 9:17 am
YYT
-
MDW
20h 47m
2 stops
WestJet Logo
9:59 am - 6:45 am
MDW
-
YYT
18h 16m
2 stops
$943WestJet
Wed, Sep 2 - Sun, Sep 6
Multiple Airlines Logo
4:00 pm - 9:45 am
YYT
-
MDW
20h 15m
3 stops
Multiple Airlines Logo
10:20 am - 12:55 am
MDW
-
YYT
12h 05m
2 stops
$946Multiple Airlines
Sun, Aug 9 - Sun, Aug 16
Multiple Airlines Logo
4:00 pm - 9:45 am
YYT
-
MDW
20h 15m
3 stops
Multiple Airlines Logo
3:15 pm - 3:05 pm
MDW
-
YYT
21h 20m
3 stops
$979Multiple Airlines
Sun, Aug 9 - Sun, Aug 16
Delta Logo
3:00 pm - 6:19 pm
YYT
-
MDW
29h 49m
2 stops
Delta Logo
7:01 pm - 10:55 pm
MDW
-
YYT
25h 24m
2 stops
$1,002Delta
Thu, Sep 10 - Mon, Sep 14
WestJet Logo
3:00 pm - 10:10 am
YYT
-
MDW
21h 40m
2 stops
WestJet Logo
5:45 pm - 6:45 am
MDW
-
YYT
34h 30m
2 stops
$1,142WestJet
Sat, Sep 5 - Wed, Sep 9
WestJet Logo
3:00 pm - 10:10 am
YYT
-
MDW
21h 40m
2 stops
WestJet Logo
5:45 pm - 6:45 am
MDW
-
YYT
34h 30m
2 stops
$1,143WestJet
Sat, Sep 5 - Wed, Sep 9

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Delta flights from Newfoundland and Labrador to Chicago

Our best Delta deals on Newfoundland and Labrador to Chicago flight tickets
Delta
Sep 10
YYT3:00 pmSt John's
29h 49m
2 stops
MDW6:19 pmChicago Midway
Sep 14
MDW7:01 pmChicago Midway
25h 24m
2 stops
YYT10:55 pmSt John's
$844
Delta
Sep 10
YYT3:00 pmSt John's
29h 49m
2 stops
MDW6:19 pmChicago Midway
Sep 14
MDW7:01 pmChicago Midway
25h 24m
2 stops
YYT10:55 pmSt John's
$1,002

Porter Airlines flights from Newfoundland and Labrador to Chicago

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago flight tickets
Porter Airlines
Aug 23
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Aug 30
MDW3:15 pmChicago Midway
7h 10m
2 stops
YYT12:55 amSt John's
$538
Porter Airlines
Aug 23
YYT4:00 pmSt John's
20h 15m
3 stops
MDW9:45 amChicago Midway
Aug 30
MDW10:20 amChicago Midway
12h 05m
2 stops
YYT12:55 amSt John's
$628
Porter Airlines
Aug 9
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Aug 16
MDW10:20 amChicago Midway
12h 05m
2 stops
YYT12:55 amSt John's
$714

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 July 11, 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
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 8/23

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sun 8/30

3:15 pm-12:55 am

2 stops7h 10m

$538

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 8/23

4:00 pm-9:45 am

3 stops20h 15m

Chicago Midway

Sun 8/30

10:20 am-12:55 am

2 stops12h 05m

$628

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 8/9

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sun 8/16

10:20 am-12:55 am

2 stops12h 05m

$714

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 9/10

3:00 pm-6:19 pm

2 stops29h 49m

Chicago Midway

Mon 9/14

7:01 pm-10:55 pm

2 stops25h 24m

$844

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 9/2

3:00 pm-9:17 am

2 stops20h 47m

Chicago Midway

Sun 9/6

9:59 am-6:45 am

2 stops18h 16m

$943

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 8/9

4:00 pm-9:45 am

3 stops20h 15m

Chicago Midway

Sun 8/16

10:20 am-12:55 am

2 stops12h 05m

$946

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 8/9

4:00 pm-9:45 am

3 stops20h 15m

Chicago Midway

Sun 8/16

3:15 pm-3:05 pm

3 stops21h 20m

$979

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 9/10

3:00 pm-6:19 pm

2 stops29h 49m

Chicago Midway

Mon 9/14

7:01 pm-10:55 pm

2 stops25h 24m

$1,002

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 9/5

3:00 pm-10:10 am

2 stops21h 40m

Chicago Midway

Wed 9/9

5:45 pm-6:45 am

2 stops34h 30m

$1,142

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 9/5

3:00 pm-10:10 am

2 stops21h 40m

Chicago Midway

Wed 9/9

5:45 pm-6:45 am

2 stops34h 30m

$1,143

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 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

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