Cheap flights from Toronto to Chicago Midway Airport from C$ 227
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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
The best prices from Toronto to Chicago Midway are usually found in July or March, booked 24 days in advance, depart on a Wednesday or Tuesday and return on a Monday
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 21 January 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 21 January 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 21 January 2025.
Find flights from Toronto to Midway within your budget
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 21 January 2025.
Fly from
Fly to
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 13/2
11:20 a.m.-12:10 p.m.
Nonstop1h 50m
Chicago Midway
Mon 17/2
1:05 p.m.-3:47 p.m.
Nonstop1h 42m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 13/2
11:20 a.m.-12:10 p.m.
Nonstop1h 50m
Chicago Midway
Wed 19/2
1:05 p.m.-3:47 p.m.
Nonstop1h 42m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 26/2
11:20 a.m.-6:23 p.m.
1 stop8h 03m
Chicago Midway
Sun 2/3
11:15 a.m.-1:57 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 21/3
6:00 a.m.-8:45 a.m.
1 stop3h 45m
Chicago Midway
Tue 25/3
1:16 p.m.-10:59 p.m.
1 stop8h 43m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Tue 1/4
2:45 p.m.-6:18 p.m.
1 stop4h 33m
Chicago Midway
Fri 4/4
1:15 p.m.-1:35 p.m.
1 stop23h 20m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Wed 16/4
8:00 p.m.-3:16 p.m.
2 stops20h 16m
Chicago Midway
Sun 20/4
12:46 p.m.-12:44 a.m.
1 stop10h 58m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sat 26/4
9:45 a.m.-12:30 p.m.
1 stop3h 45m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sun 4/5
3:30 p.m.-4:20 p.m.
Nonstop1h 50m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Mon 27/1
7:00 a.m.-3:02 p.m.
1 stop9h 02m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 13/2
6:30 a.m.-12:42 p.m.
1 stop7h 12m
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.
Travel insights for flights from Toronto to Midway
Get recent, data-driven insights about flights from Toronto to Midway including ideal travel times, pricing trends, and more.
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 17 January 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 24 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 21 January 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 evening, which can drop the price by up to 37% 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 Monday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 21 January 2025.
Read reviews from past customers who have flown Porter Airlines and WestJet 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.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
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 21 January 2025.
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How does Cheapflights help users find flights from Toronto to Midway?
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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.