Cheap Flights From Billy Bishop Toronto City (YTZ) To Midway Intl. (MDW)

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Cheapest Flights from Toronto (YTZ) to Chicago (MDW)

The cheapest flights to Midway Intl. found within the past 7 days were CA $321 round trip and CA $191 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 9 - Sat, Sep 12
YTZ
Toronto
MDW
Chicago
CA $321 Roundtrip, just found
CA $321
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Sep 9 from Toronto to Chicago, returning Sat, Sep 12, priced at CA $321 just found
Sat, Sep 5 - Tue, Sep 8
YTZ
Toronto
MDW
Chicago
CA $343 Roundtrip, just found
CA $343
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Sep 5 from Toronto to Chicago, returning Tue, Sep 8, priced at CA $343 just found
Wed, Sep 9 - Sat, Sep 12
YTZ
Toronto
MDW
Chicago
CA $352 Roundtrip, just found
CA $352
Roundtrip
just found
Select Air Transat flight, departing Wed, Sep 9 from Toronto to Chicago, returning Sat, Sep 12, priced at CA $352 just found
Mon, Aug 31 - Wed, Sep 9
YTZ
Toronto
MDW
Chicago
CA $354 Roundtrip, found 1 day ago
CA $354
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Aug 31 from Toronto to Chicago, returning Wed, Sep 9, priced at CA $354 found 1 day ago
Mon, Aug 31 - Sun, Sep 13
YTZ
Toronto
MDW
Chicago
CA $359 Roundtrip, found 17 hours ago
CA $359
Roundtrip
found 17 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Toronto to Chicago, returning Sun, Sep 13, priced at CA $359 found 17 hours ago
Wed, Sep 9 - Sat, Sep 12
YTZ
Toronto
MDW
Chicago
CA $361 Roundtrip, just found
CA $361
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Sep 9 from Toronto to Chicago, returning Sat, Sep 12, priced at CA $361 just found
Wed, Sep 9 - Sat, Sep 12
YTZ
Toronto
MDW
Chicago
CA $364 Roundtrip, just found
CA $364
Roundtrip
just found
Select Air Transat flight, departing Wed, Sep 9 from Toronto to Chicago, returning Sat, Sep 12, priced at CA $364 just found
Fri, Sep 11 - Sun, Sep 13
YTZ
Toronto
MDW
Chicago
CA $365 Roundtrip, found 3 hours ago
CA $365
Roundtrip
found 3 hours ago
Select Porter Airlines flight, departing Fri, Sep 11 from Toronto to Chicago, returning Sun, Sep 13, priced at CA $365 found 3 hours ago
Sat, Aug 29 - Wed, Sep 9
YTZ
Toronto
MDW
Chicago
CA $374 Roundtrip, found 19 hours ago
CA $374
Roundtrip
found 19 hours ago
Select Porter Airlines flight, departing Sat, Aug 29 from Toronto to Chicago, returning Wed, Sep 9, priced at CA $374 found 19 hours ago
Sat, Sep 5 - Tue, Sep 8
YTZ
Toronto
MDW
Chicago
CA $374 Roundtrip, just found
CA $374
Roundtrip
just found
Select Air Transat flight, departing Sat, Sep 5 from Toronto to Chicago, returning Tue, Sep 8, priced at CA $374 just found

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $1,126, price is now CA $762 per person
CA $762
per person
Sep 24 - Sep 26
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $2,285, price is now CA $1,569 per person
CA $1,569
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was CA $1,526, price is now CA $1,062 per person
CA $1,062
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was CA $1,974, price is now CA $1,405 per person
CA $1,405
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $2,021, price is now CA $1,440 per person
CA $1,440
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from Billy Bishop Toronto City Airport (YTZ) to Midway Airport?
If you're not so fond of layovers, it's smart to plan your flight from YTZ to MDW as early as possible. Porter Airlines is the only carrier that offers direct flights to Chicago from Toronto.
What airlines fly from Billy Bishop Airport to Midway Intl. Airport (MDW)?
Ready to book the airfare for your next big adventure? Want to travel from Billy Bishop Airport to Chicago Airport in the shortest time possible? Hop on one of the 65 direct flights offered by Porter Airlines every month, and you'll be landing before you can utter 'Are we there yet?'
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.