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Cheap flights from St. John's to Chicago from $655

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 5/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
3:00 pm - 4:24 pm
YYT
-
MDW
27h 54m2 stops
Porter Airlines Logo
9:40 am - 12:28 am
MDW
-
YYT
12h 18m2 stops
$655Porter Airlines
Sat, May 30 - Wed, Jun 3
Porter Airlines Logo
1:10 pm - 8:45 am
YYT
-
MDW
22h 05m2 stops
Porter Airlines Logo
9:40 am - 12:28 am
MDW
-
YYT
12h 18m2 stops
$666Porter Airlines
Sat, May 30 - Wed, Jun 3
Porter Airlines Logo
3:00 pm - 4:24 pm
YYT
-
MDW
27h 54m2 stops
Porter Airlines Logo
9:40 am - 12:28 am
MDW
-
YYT
12h 18m2 stops
$670Porter Airlines
Sat, May 30 - Wed, Jun 3

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
May 30
YYT3:00 pmSt John's
27h 54m
2 stops
MDW4:24 pmChicago Midway
Jun 3
MDW9:40 amChicago Midway
12h 18m
2 stops
YYT12:28 amSt John's
$655
Find similar
Porter Airlines
May 30
YYT1:10 pmSt John's
22h 05m
2 stops
MDW8:45 amChicago Midway
Jun 3
MDW9:40 amChicago Midway
12h 18m
2 stops
YYT12:28 amSt John's
$666
Find similar
Porter Airlines
May 30
YYT3:00 pmSt John's
27h 54m
2 stops
MDW4:24 pmChicago Midway
Jun 3
MDW9:40 amChicago Midway
12h 18m
2 stops
YYT12:28 amSt John's
$670
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 December 18, 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

Sat 5/30

3:00 pm-4:24 pm

2 stops27h 54m

Chicago Midway

Wed 6/3

9:40 am-12:28 am

2 stops12h 18m

$655

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 5/30

1:10 pm-8:45 am

2 stops22h 05m

Chicago Midway

Wed 6/3

9:40 am-12:28 am

2 stops12h 18m

$666

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 5/30

3:00 pm-4:24 pm

2 stops27h 54m

Chicago Midway

Wed 6/3

9:40 am-12:28 am

2 stops12h 18m

$670

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

Fastest flight time

11h 50m

Direct flights

None
The fastest flight from St. John's to Chicago Midway Airport takes 11h 50m
There are no direct flights from St. John's to Chicago Midway Airport. There are no popular flight routes from St. John's to Chicago Midway Airport.
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  • 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 50m.

  • 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 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.

I’m not ready to book a flight from St. John's to Chicago right now. Can momondo alert me if prices change?

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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