Cheap flights from Toronto to Chicago Midway Airport from C$ 148
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
Cheapflights Tip: The best prices from Toronto to Chicago Midway are usually found in May or February, booked 34 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday
Cheap flight deals from Toronto to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 12 June 2025.
Find flight deals from Toronto to Midway
Cheapest flights from Toronto to MidwayExplore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.
Explore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.
Cheapflights Fare Finder
Customize your flight search to find flights from Toronto to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 12 June 2025.
Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 26/6
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
Chicago Midway
Sun 29/6
9:40 a.m.-12:22 p.m.
Nonstop1h 42m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 26/6
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
Chicago Midway
Mon 30/6
9:40 a.m.-12:20 p.m.
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 18/8
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
Chicago Midway
Tue 19/8
5:20 p.m.-8:02 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sat 4/10
12:15 p.m.-6:36 p.m.
1 stop7h 21m
Chicago Midway
Wed 15/10
9:30 a.m.-5:23 p.m.
1 stop6h 53m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 17/7
1:04 p.m.-5:39 p.m.
1 stop5h 35m
Chicago Midway
Thu 24/7
6:20 p.m.-10:58 p.m.
1 stop3h 38m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Tue 22/7
6:30 p.m.-9:45 a.m.
2 stops16h 15m
Chicago Midway
Tue 29/7
1:46 p.m.-6:14 a.m.
2 stops15h 28m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 21/7
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 4/7
3:35 p.m.-4:24 p.m.
Nonstop1h 49m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sat 6/9
12:14 p.m.-6:37 p.m.
1 stop7h 23m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sun 22/6
6:30 a.m.-12:29 p.m.
1 stop6h 59m
Best time to book a flight from Toronto to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Toronto to Chicago Midway Airport
How far ahead should I book a flight from Toronto to Chicago Midway Airport?
Use this chart to determine the optimal time to book a round-trip flight from Toronto to Midway. Price data was last updated on 9 June 2025.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago Midway Airport, you should look to book at least 34 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Toronto to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 243). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YTO to MDW?
Find hourly flight availability from Toronto to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 June 2025.
When flying from Toronto to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 42% versus a flight at noon.
What is the cheapest day to fly from Toronto to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Toronto to Midway. Price data was last updated on 30 June 2024.
Travelers seeking maximum savings on their Toronto to Chicago Midway Airport flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Toronto to Chicago Midway Airport
Explore weekly flight availability from Toronto to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 12 June 2025.
The most flights from YTO to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 12 June 2025.
Read reviews from past customers who have flown Porter Airlines, Delta and KLM 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
Overall
Boarding
Food
Crew
Comfort
Reviews
Mary,Jun 2025
FLL - YYZ
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
Mary,Jun 2025
FLL - YYZ
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
Mary,Jun 2025
FLL - YYZ
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
Mary,Jun 2025
FLL - YYZ
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
Mary,Jun 2025
FLL - YYZ
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
Mary,Jun 2025
FLL - YYZ
Related info for your journey
Find useful and relevant information for your journey from Toronto to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 2 airlines flying from Toronto to Midway
Discover the top 2 airlines that operate flights from Toronto to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 12 June 2025.
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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 offers price alerts on Toronto to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.