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YYT - MDW

$278 Find cheap flights from St. John's to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from St. John's to Midway departing on 5/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 6/9
Sun 6/16

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from St. John's to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from St. John's to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,156,178 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from St. John's to Midway (YYT-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from St. John's to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:40 pm - 9:37 pmYYT-MDW
8h 27m2 stops
8:00 am - 6:25 pmMDW-YYT
7h 55m2 stops
$452Porter Airlines
Find Deal
Fri, Jun 7 - Tue, Jun 11
6:00 am - 4:17 pmYYT-MDW
12h 47m2 stops
8:00 am - 6:25 pmMDW-YYT
7h 55m2 stops
$453Porter Airlines
Find Deal
Fri, Jun 7 - Tue, Jun 11
3:35 pm - 9:37 pmYYT-MDW
8h 32m2 stops
11:05 am - 11:35 pmMDW-YYT
10h 00m2 stops
$578Porter Airlines
Find Deal
Fri, May 24 - Mon, May 27
7:00 am - 4:17 pmYYT-MDW
11h 47m2 stops
5:15 pm - 3:56 amMDW-YYT
8h 11m1 stop
$584Porter Airlines
Find Deal
Fri, May 24 - Mon, May 27

Good to know

Cheapest flight

$278
Flight from St. John's to Chicago

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

Are your dates flexible? Find out the best times to travel from St. John's to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking St. John's to Chicago flights

  • What is the cheapest flight from St. John's to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from St. John's to Chicago Midway Airport was $278 for a one-way ticket and $452 for a round-trip.

  • Do I need a passport to fly between St. John's and Chicago?

    Yes

  • Which airports will I be using when flying from St. John's to Chicago?

    St. John's and Chicago are both served by 1 main airport. You will leave St. John's from St John's and will be arriving at Chicago Midway.

  • Which aircraft models fly most regularly from St. John's to Chicago?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from St. John's to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from St. John's to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from St. John's to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from St. John's is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from St. John's to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to St. John's with another airline. Booking your flights between St. John's and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from St. John's to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from St. John's up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from St. John's to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from St. John's to Chicago found on KAYAK in the last 72 hours.
5/26Sun
1 stop
12h 10mYYT-MDW
$278
5/25Sat
1 stop
18h 32mYYT-MDW
$291
5/26Sun
3 stopsPorter Airlines
17h 07mYYT-MDW
$302
5/25Sat
2 stopsPorter Airlines
14h 32mYYT-MDW
$318
5/26Sun
2 stopsPorter Airlines
11h 47mYYT-MDW
$319
5/25Sat
3 stopsPorter Airlines
23h 52mYYT-MDW
$340

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St. John's - Chicago Flights

Departure:

St. John's (undefined)Canada

Destination:

Chicago (MDW)United States

Return flight deals:

Chicago - St. John's

Cabin classes: