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$295+ Cheap flights from St. John's (YYT) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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1. Tell us where you want to go

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Cheap flight deals from St. John's to Midway

Discover tips and strategies to find the most affordable flight options for your journey from St. John's (YYT) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$506
(Porter Airlines)

One-way from

$295
(Mytrip)
Provider with most accurate pricing for St John's-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for St John's-Chicago Midway flights.
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From St John's to Chicago Midway
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One-way flight from St John's to Chicago Midway
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Find flight deals from St. John's to Midway

Best flights from St. John's to Midway
Discover carefully curated flight deals from St. John's to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 26, 2025.

This Porter Airlines deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:20 amYYT - MDW
2 stops8h 00mPorter Airlines
Wed 4/2211:00 amMDW - YYT
2 stops9h 35mPorter Airlines
Deal found 11/23$506

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. John's to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated November 26, 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

St. John's

Fly to

Midway

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 4/18

6:20 am-11:50 am

2 stops8h 00m

Chicago Midway

Wed 4/22

11:00 am-11:05 pm

2 stops9h 35m

$506

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 12/29

6:20 am-3:20 pm

2 stops11h 30m

$295

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 12/28

6:20 am-3:20 pm

2 stops11h 30m

$345

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 12/30

6:20 am-10:12 pm

3 stops42h 22m

$424

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 12/29

3:35 pm-9:58 pm

1 stop32h 53m

$434

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 12/30

6:00 am-3:20 pm

2 stops11h 50m

$436

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 12/2

6:20 am-8:46 am

3 stops28h 56m

$446

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 12/2

6:20 am-10:05 am

2 stops30h 15m

$539

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 12/2

9:45 am-6:18 pm

2 stops35h 03m

$573

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Compare providers for flights from St. John's to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from St. John's to Midway in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on St. John's-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on St. John's-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from St. John's-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on St. John's-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for St. John's-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from St. John's to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from St. John's with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from St. John's to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from St. John's to Chicago Midway?

    St John's (YYT), located 4.2 mi from the city center, is the airport you fly out of when you book flights from St. John's to Chicago Midway. 0 airlines have flights from St John's to Chicago Midway on a regular basis. Booking flights from St John's to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from St. John's to Chicago Midway Airport?

    Porter Airlines can get you from St. John's to Chicago Midway Airport in just under 8h. Your travel time can differ by up to . The distance from St. John's to Chicago Midway Airport is about 1748 mi.

  • Can I find deals for flights from St. John's to Midway that include hotel bookings?

    Yes. In addition to deals on St. John's to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St. John's to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. John's to Midway.

  • Can I find deals for business class flights from St. John's to Midway?

    Yes. Cheapflights offers flight deals from St. John's to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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