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Cheap flights from St. John's to Chicago from $433

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from St. John's to Chicago departing on 12/10. 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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Cheap round-trip flights

Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m3 stops
Porter Airlines Logo
11:00 am - 11:05 pmMDW-YYT
9h 35m3 stops
$433Porter Airlines
Find Deal
mié., dic. 10 - lun., dic. 15
Porter Airlines Logo
6:20 am - 3:20 pmYYT-MDW
11h 30m2 stops
Porter Airlines Logo
11:00 am - 11:05 pmMDW-YYT
9h 35m2 stops
$476Porter Airlines
Find Deal
jue., dic. 11 - lun., dic. 15
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m3 stops
Porter Airlines Logo
11:00 am - 11:05 pmMDW-YYT
9h 35m3 stops
$477Porter Airlines
Find Deal
jue., dic. 11 - lun., dic. 15
Porter Airlines Logo
7:00 am - 4:24 pmYYT-MDW
11h 54m3 stops
Porter Airlines Logo
9:35 am - 12:38 amMDW-YYT
12h 33m2 stops
$499Porter Airlines
Find Deal
mié., sep. 17 - sáb., sep. 20
WestJet Logo
3:00 pm - 9:40 amYYT-MDW
45h 10m2 stops
WestJet Logo
11:00 am - 10:56 pmMDW-YYT
9h 26m2 stops
$529WestJet
Find Deal
mié., sep. 17 - sáb., sep. 20
WestJet Logo
3:00 pm - 9:40 amYYT-MDW
45h 10m2 stops
WestJet Logo
12:43 pm - 10:56 pmMDW-YYT
31h 43m2 stops
$560WestJet
Find Deal
mar., sep. 9 - vie., sep. 12
Porter Airlines Logo
6:20 am - 10:05 amYYT-MDW
30h 15m2 stops
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
$561Porter Airlines
Find Deal
mié., dic. 10 - lun., dic. 15

Porter Airlines flights from St. John's to Chicago Midway Airport

Our best Porter Airlines deals on St. John's to Chicago Midway Airport flight tickets
Porter Airlines
Dec 10
YYT6:00 amSt John's
11h 50m
3 stops
MDW3:20 pmChicago Midway
Dec 15
MDW11:00 amChicago Midway
9h 35m
3 stops
YYT11:05 pmSt John's
$433
Find similar
Porter Airlines
Dec 11
YYT6:20 amSt John's
11h 30m
2 stops
MDW3:20 pmChicago Midway
Dec 15
MDW11:00 amChicago Midway
9h 35m
2 stops
YYT11:05 pmSt John's
$476
Find similar
Porter Airlines
Dec 11
YYT6:00 amSt John's
11h 50m
3 stops
MDW3:20 pmChicago Midway
Dec 15
MDW11:00 amChicago Midway
9h 35m
3 stops
YYT11:05 pmSt John's
$477
Find similar

WestJet flights from St. John's to Chicago Midway Airport

Our best WestJet deals on St. John's to Chicago Midway Airport flight tickets
WestJet
Sep 17
YYT3:00 pmSt John's
45h 10m
2 stops
MDW9:40 amChicago Midway
Sep 20
MDW11:00 amChicago Midway
9h 26m
2 stops
YYT10:56 pmSt John's
$529
Find similar
WestJet
Sep 9
YYT3:00 pmSt John's
45h 10m
2 stops
MDW9:40 amChicago Midway
Sep 12
MDW12:43 pmChicago Midway
31h 43m
2 stops
YYT10:56 pmSt John's
$560
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from St. John's 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 julio 31, 2025.
Use the filters below to find and compare flights from St. John's 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

mié. 12/10

6:00 am-3:20 pm

3 stops11h 50m

Chicago Midway

lun. 12/15

11:00 am-11:05 pm

3 stops9h 35m

$433

St. John'sChicago

YYT - MDW

YYTMDW

St John's

jue. 12/11

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

lun. 12/15

11:00 am-11:05 pm

2 stops9h 35m

$476

St. John'sChicago

YYT - MDW

YYTMDW

St John's

jue. 12/11

6:00 am-3:20 pm

3 stops11h 50m

Chicago Midway

lun. 12/15

11:00 am-11:05 pm

3 stops9h 35m

$477

St. John'sChicago

YYT - MDW

YYTMDW

St John's

mié. 9/17

7:00 am-4:24 pm

3 stops11h 54m

Chicago Midway

sáb. 9/20

9:35 am-12:38 am

2 stops12h 33m

$499

St. John'sChicago

YYT - MDW

YYTMDW

St John's

mié. 9/17

3:00 pm-9:40 am

2 stops45h 10m

Chicago Midway

sáb. 9/20

11:00 am-10:56 pm

2 stops9h 26m

$529

St. John'sChicago

YYT - MDW

YYTMDW

St John's

mar. 9/9

3:00 pm-9:40 am

2 stops45h 10m

Chicago Midway

vie. 9/12

12:43 pm-10:56 pm

2 stops31h 43m

$560

St. John'sChicago

YYT - MDW

YYTMDW

St John's

mié. 12/10

6:20 am-10:05 am

2 stops30h 15m

Chicago Midway

lun. 12/15

11:00 am-1:01 am

2 stops11h 31m

$561

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from St. John's to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from St. John's to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap St. John's to Chicago Midway Airport (YYT to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. John's to Chicago Midway Airport

Best Price Found

$433

Fastest flight time

11h 30m

Direct flights

None
The best flight deal from St. John's to Chicago Midway Airport found on momondo in the last 72 hours is $433
The fastest flight from St. John's to Chicago Midway Airport takes 11h 30m
There are no direct flights from St. John's to Chicago Midway Airport. Popular non-direct route for this connection is St John's Airport - Chicago Midway Airport.
Search flight deals

  • How far is St John's to Chicago Midway by plane?

    The straight-line distance from St John's to Chicago Midway is 1749.9 mi. A reasonable flight in good conditions will take 11h 30m.

  • When did momondo last update prices for flights from St John's Airport to Chicago Midway Airport?

    Prices for flights from St John's Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from St John's Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from St John's Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport 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 Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • How do I get Price Alerts for flights from St. John's to Chicago Midway Airport?

    Search flight deals from St. John's to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from St. John's to Chicago Midway Airport with momondo?

    With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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Why use momondo?

Why should I use momondo to find a flight deal from St. John's to Chicago?

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Can I find flights from St. John's to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from St. John's with this policy.

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Once all potential St. John's to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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Of course. momondo tracks the price of St. John's to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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