Skip to main content
Beginning of main content

YYZ (Toronto) to MDW (Chicago) Flights $221.28

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Here are your best fares found in the past 7 days

The lowest fare found for this route is $263.3 on Tue, Sep 19 from YYZ to MDW
Flights Fare Calendar Find minimum fare between origin YYZ and destination MDW Click this button to get previous 30 days data Click this button to get next 30 days data $809 $693 $578 $462 $346 $231 $115 $0 Jun Jul 27 28 29 30 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 1 2 3 4 5 6 7 8 9 10 11 12 13 14 T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S Price is $ 693.61 on Delta Price is $ 667.66 on Delta Price is $ 641.86 on Delta Price is $ 621.9 on Delta Price is $ 615.14 on Delta Price is $ 604.68 on Delta Price is $ 583.53 on Delta Price is $ 578.83 on Delta Price is $ 573.42 on Delta Price is $ 539.63 on Delta Price is $ 538.68 on Delta Price is $ 538.68 on Delta Price is $ 538.32 on Delta Price is $ 519.18 on Delta Price is $ 496.85 on Delta Price is $ 483.16 on Delta Price is $ 480.09 on Delta Price is $ 480.09 on Delta Price is $ 473.28 on Delta Price is $ 469.36 on Delta Price is $ 464.4 on Delta Price is $ 444.1 on Delta Price is $ 442.72 on Delta Price is $ 441.92 on Delta Price is $ 441.92 on Delta Price is $ 440.63 on Delta Price is $ 432.82 on Delta Price is $ 422.64 on Delta Price is $ 408.95 on Delta Price is $ 406.97 on Delta Price is $ 406.87 on Delta Price is $ 406.87 on Delta Price is $ 404.76 on Delta Price is $ 397.95 on Delta Price is $ 370.99 on Delta Price is $ 367.68 on Delta Price is $ 367.67 on Delta Price is $ 357.5 on Delta Price is $ 356.33 on Delta Price is $ 348.52 on Delta Price is $ 313.64 on Delta Price is $ 311.28 on Delta Price is $ 291.9 on Delta Price is $ 263.3 on Delta

Cheap YYZ to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$197.16

Local Weather Chicago
June 84° 57°
July 85° 67°
August 83° 64°

Interesting Facts About Flights from Toronto to Chicago (YYZ to MDW)

Question : How often is the Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) route delayed?
Answer : This particular route gets passengers to Chicago Midway International Airport on time 27% of the time, which puts it in the 22nd percentile worldwide. When there is a delay, it averages 23 minutes.

Question : Have you considered flying out of an airport besides Pearson International Airport (YYZ)?
Answer : Lucky for you, there is another airport near Toronto. Toronto City Centre Airport (YTZ) is 11 miles away, and over the next few months, flights are being priced 47% cheaper than flights from Pearson International Airport.

Question : How much should a trip from Toronto (YYZ) to Chicago (MDW) cost?
Answer : Flight prices fluctuate much more than most routes from Canada for YYZ to MDW. They range anywhere from $221 to $759. Remember, the sooner you book, the more you'll be able to save.

Question : Would you be willing to change your travel days if it saved you money?
Answer : Monday is your lowest-cost day to fly in July. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Which airline is offering the cheapest flight from YYZ to MDW?
Answer : Delta Air Lines is the leader in keeping prices down for their passengers over the next three months. Fares are being booked at just $221 and, when compared to the high-end bookings of $759, it's quite a deal.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : Jul 7th has seen bookings (as of Jun 26th) as cheap as $519. That comes in 12% below the average price for this route. Saving now means you'll have more money in your hand for the trip.

Question : Which airline can you expect delays with on this route?
Answer : 100% of Skycharter flights from Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) are late. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.