Cheap flights from Toronto to Chicago Midway Airport from C$ 182
This is the cheapest one-way flight price, found on 26/9. Prices may vary by date and flight preferences.
How to find the cheapest flight from Toronto (YTO) to Midway (MDW)
All the information you need to plan the best YTO to MDW flight in 2023: compare Toronto to Midway flight prices with the expected peak season, weather and rainfall in Midway.
Popular in | October |
|---|---|
Cheapest in | September |
Round-trip from | C$ 468 |
One-way from | C$ 197 |
YTO - CHI Price | C$ 347 - C$ 613 |
|---|---|
CHI Temperature | -5 - 23 °C |
CHI Rainfall | 43 - 125 mm |
How far in advance should I book a flight from Toronto to Chicago Midway Airport?
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 60 days in advance, which can save you up to 49% on flights from Toronto to Chicago Midway Airport compared to booking the week you need them. Waiting 60 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 390. For sooner than that we have options available in the next 3 days from C$ 494.
What is the cheapest month to fly from Toronto to Chicago Midway Airport?
June can be a great time to fly to Chicago Midway Airport from Toronto with a flight ticket averaging about C$ 343. Cheapflights users have found deals in the month of June for as cheap as C$ 219. The most expensive prices can be found in the month of March.
When is the cheapest time to fly from Toronto to Chicago Midway Airport (YTO - MDW)?
When flying from Toronto to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Cheap Delta flights from Toronto to Midway
Take a look at some of the lowest-priced Delta flights heading from Toronto to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Cheap WestJet flights from Toronto to Midway
Some of the lowest-priced WestJet flights we've found at this time heading from Toronto to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Cheap Toronto to Midway flights in September & October 2023
The best prices found for YTO to MDW flights for September, October
Scroll through some of the best deals on flights from Toronto to Chicago in 2023. Check back in a little while for more flight options.
Toronto to Midway 2023 flight deals
Cheap flights to Midway from Toronto found for this year
Scroll through some of the best deals on flights from Toronto to Chicago in 2023. Check back in a little while for more flight options.
Direct flights to Midway from Toronto
Save time with Toronto to Midway direct flight deals
If you're seeking options on non-stop flights from Toronto to Chicago, check out these fares. Search for alternative flights from Toronto to Chicago by utilizing the search form above.
Toronto to Midway flights leaving soon
Late deals on round-trip flights to Midway from Toronto, departing today and this week
Consider one of these great deals we found on last-minute flights from Toronto to Chicago. Users should examine the flight details to ensure there are no surprises.
One-way flights to Midway from Toronto
The cheapest one-way flights from Toronto to Midway
Users in need of a one-way flight from Toronto to Chicago can choose from these deals. Users in need of a round-trip flight from Toronto to Chicago instead should update the search form at the top of page.
Find flights from Toronto to Midway within your budget
Use the slider to find flights from Toronto to Midway that fit your budget.
Fly from
Fly to
Budget
C$ 293 - C$ 756
Route
Depart
Return
Price
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 1/12
1 stop10h 10m
Chicago Midway
Mon 4/12
1 stop13h 14m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 10/11
1 stop20h 08m
Chicago Midway
Sun 12/11
2 stops10h 18m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 20/10
Nonstop1h 47m
Chicago Midway
Tue 24/10
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 19/10
Nonstop1h 47m
Chicago Midway
Wed 22/11
Nonstop1h 42m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sun 5/11
1 stop11h 16m
Chicago Midway
Mon 6/11
1 stop7h 15m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 1/12
Nonstop1h 50m
Chicago Midway
Sun 3/12
Nonstop1h 42m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 19/10
1 stop7h 34m
Chicago Midway
Tue 24/10
1 stop4h 30m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 17/11
1 stop5h 08m
Chicago Midway
Sun 19/11
1 stop4h 34m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Wed 1/11
1 stop3h 26m
Chicago Midway
Wed 1/11
1 stop5h 20m
Reviews of airlines servicing Midway
Read reviews from past customers who have flown Delta, WestJet and Porter Airlines from Toronto to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Comfort
Boarding
Crew
Food
Overall
Reviews
Pros: Overall great flight
Cons: The people in front of us were over served and loud
Entertainment
Comfort
Boarding
Crew
Food
Overall
Reviews
Pros: Overall great flight
Cons: The people in front of us were over served and loud
Entertainment
Comfort
Boarding
Crew
Food
Overall
Reviews
Pros: Overall great flight
Cons: The people in front of us were over served and loud
Entertainment
Comfort
Boarding
Crew
Food
Overall
Reviews
Pros: Overall great flight
Cons: The people in front of us were over served and loud
Entertainment
Comfort
Boarding
Crew
Food
Overall
Reviews
Pros: Overall great flight
Cons: The people in front of us were over served and loud
Entertainment
Comfort
Boarding
Crew
Food
Overall
Reviews
Pros: Overall great flight
Cons: The people in front of us were over served and loud
Related info for your journey
Useful info, stats and facts about Toronto to Midway flights.
Can I find flights from Toronto to Chicago Midway Airport for under C$ 300 on Cheapflights?
Yes, there are multiple flights from Toronto to Chicago Midway Airport for under C$ 300. The cheapest flight booked recently is on Multiple Airlines for just C$ 293, but on average you can expect to pay C$ 360.
Are there direct flights from Toronto to Chicago Midway Airport for under C$ 400 on Cheapflights?
Cheapflights has 20 direct flights from Toronto to Chicago Midway Airport under C$ 400. A good price for a direct flight from Toronto to Chicago Midway Airport is less than C$ 374.
Are there last-minute flights available from Toronto to Chicago Midway Airport for under C$ 600?
There are currently 20+ open flights from Toronto to Chicago Midway Airport within the next 7 days for less than C$ 600.
What is the cheapest airline to fly from Toronto to Chicago Midway Airport round-trip?
Porter Airlines, at C$ 347, was found to be the cheapest airline from Toronto to Chicago Midway Airport..
What are the most popular airlines that fly from Toronto to Chicago Midway Airport?
Before booking your flight from Toronto to Chicago Midway Airport check out the most popular airlines for this route: Endeavor Airlines, Air Canada or Porter Airlines.
What does YYZ to MDW mean?
Toronto Pearson Intl Airport is YYZ and Chicago Midway Airport is MDW. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Toronto Island Airport (YTZ), Hamilton Airport (YHM), Toronto Kitchener-Waterloo Airport (YKF) are other airports near this flight route and their unique identifiers/IATA codes.
Other flights from Toronto
Other flights to Midway
Flights to Midway from Toronto
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Alternative routes for Toronto to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Toronto to Midway
The chart below displays the airlines Cheapflights users travelling from Toronto to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Hourly flight availability from Toronto to Midway
See what time of day planes typically take off from Toronto to Midway
| 1%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 45%of flight departures | Morning6 am to noon |
| 54%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Weekly flight availability from Toronto to Midway
See how many times per day planes take to the skies headed from Toronto to Midway
| Sunday | 1daily flight |
|---|---|
| Monday | 2daily flights |
| Tuesday | 2daily flights |
| Wednesday | 2daily flights |
| Thursday | 3daily flights |
| Friday | 3daily flights |
| Saturday | 1daily flight |
Fly with Cheapflights
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How does Cheapflights help users find flights from Toronto to Midway?
When you search for this flight from Toronto to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from Toronto to Midway?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Toronto to Midway.
Can Cheapflights find flights from Toronto to Midway with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Toronto to Midway flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Toronto to Midway become cheaper?
Yes, Cheapflights does offer price alerts on Toronto to Midway flights so you can book your travels when it’s right. The Price Alert feature is available after a flight search is performed above.