YYT - MDW
$315 Find Cheap Flights from St. John's to Chicago - Compare and Save
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 Chicago departing on 11/22. 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.
Everything you should know
Cheapest round-trip
$1,069
Typical prices: $710-$710
Multiple Airlines
Tue 10/23Sun 10/28
YYT - MDW • 1 stop
Cheap Flights from St. John's to Chicago (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 Chicago 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.
Cheap flights from St. John's to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.
Fri, Oct 23 - Wed, Oct 28
1:20 pm - 2:35 pmYYT St John's-MDW Chicago Midway
27h 45m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,069Multiple Airlines
Fri, Oct 23 - Tue, Oct 27
1:20 pm - 2:35 pmYYT St John's-MDW Chicago Midway
27h 45m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,080Multiple Airlines
Thu, Oct 22 - Wed, Oct 28
3:00 pm - 4:14 pmYYT St John's-MDW Chicago Midway
27h 44m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
12:27 pm - 9:10 amMDW Chicago Midway-YYT St John's
18h 13m2 stops Minneapolis St Paul Calgary
$1,110WestJet
Wed, Nov 4 - Sat, Nov 7
3:15 pm - 9:32 amYYT St John's-MDW Chicago Midway
20h 47m3 stops Halifax Intl Toronto Pearson Intl Detroit Metropolitan Wayne County
6:44 pm - 1:35 pmMDW Chicago Midway-YYT St John's
16h 21m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,112Multiple Airlines
Thu, Oct 22 - Wed, Oct 28
3:00 pm - 11:00 amYYT St John's-MDW Chicago Midway
22h 30m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,145Multiple Airlines
Thu, Oct 22 - Tue, Oct 27
3:00 pm - 11:00 amYYT St John's-MDW Chicago Midway
22h 30m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,156Multiple Airlines
Wed, Oct 21 - Wed, Oct 28
8:25 pm - 11:00 amYYT St John's-MDW Chicago Midway
17h 05m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,181Multiple Airlines
Wed, Oct 21 - Tue, Oct 27
8:25 pm - 11:00 amYYT St John's-MDW Chicago Midway
17h 05m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,192Multiple Airlines
Fri, Oct 23 - Thu, Oct 29
1:20 pm - 2:35 pmYYT St John's-MDW Chicago Midway
27h 45m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,267Multiple Airlines
Thu, Oct 22 - Thu, Oct 29
3:00 pm - 11:00 amYYT St John's-MDW Chicago Midway
22h 30m1 stop Toronto Pearson Intl
6:44 pm - 1:30 pmMDW Chicago Midway-YYT St John's
16h 16m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,343Multiple Airlines
Sun, Nov 22
7:00 am - 7:47 pmYYT St John's-MDW Chicago Midway
39h 17m3 stops Halifax Intl Toronto Pearson Intl Orlando
$315Multiple Airlines
Sun, Nov 22
2:30 pm - 7:47 pmYYT St John's-MDW Chicago Midway
31h 47m2 stops Toronto Pearson Intl Orlando
$321Multiple Airlines
Wed, Nov 4
2:30 pm - 11:47 pmYYT St John's-MDW Chicago Midway
35h 47m3 stops Toronto Pearson Intl New York LaGuardia Atlanta Hartsfield-Jackson
$461Multiple Airlines
Wed, Nov 4
2:30 pm - 9:32 amYYT St John's-MDW Chicago Midway
21h 32m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
$500Multiple Airlines
Price, demand and travel trends for St. John's to Chicago Midway Airport flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Key details for St. John's to Chicago Midway Airport flights
Cheapest flight | $315 |
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When to book flights from St. John's to Chicago
Are your dates flexible? Find out the best times to travel from St. John's to Chicago 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.
Your St. John's to Chicago Midway Airport flight questions, answered
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Your guide to booking St. John's to Chicago Midway Airport flights
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Cabin class types available on flights to Chicago
Cabin classes available on flights from St. John's to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
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Flights from domestic origins to Chicago
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.