C$ 115+ Cheap flights from Chicago Midway Airport
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 14/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
What to know about flights from Midway
Discover essential information about flights departing from Midway, including flight schedules, destinations, airlines operating at the Midway airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 23 October 2025.
Cheapest airline | WestJet |
|---|---|
Good round-trip deal | C$ 402 or less |
Good one-way deal | C$ 110 or less |
Find flights from Midway
Cheapest flights from MidwayExplore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 23 October 2025.
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 23 October 2025.
Find flights from Midway within your budget
Fly to
Route
Depart
Return
Price
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Sun 7/12
6:15 a.m.-3:07 p.m.
1 stop8h 52m
Winnipeg
Sun 14/12
7:30 a.m.-10:12 p.m.
1 stop14h 42m
ChicagoToronto
MDW - YTZ
MDWYTZ
Chicago Midway
Fri 16/1
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
Toronto Island
Mon 19/1
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Thu 27/11
9:34 a.m.-5:15 p.m.
1 stop6h 41m
Toronto Pearson Intl
Mon 1/12
6:05 a.m.-12:34 p.m.
1 stop7h 29m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Sat 22/11
9:32 a.m.-5:15 p.m.
1 stop6h 43m
Toronto Pearson Intl
Fri 28/11
6:05 a.m.-8:54 a.m.
1 stop3h 49m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fri 5/12
8:42 p.m.-12:41 a.m.
2 stops27h 59m
Winnipeg
Fri 12/12
7:30 a.m.-7:42 p.m.
1 stop12h 12m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Thu 4/12
9:34 a.m.-2:48 p.m.
1 stop4h 14m
Toronto Pearson Intl
Sun 7/12
6:05 a.m.-8:54 a.m.
1 stop3h 49m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Fri 21/11
6:54 p.m.-11:05 p.m.
1 stop3h 11m
Toronto Pearson Intl
Sun 23/11
12:08 p.m.-6:08 p.m.
1 stop7h 00m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Tue 18/11
9:34 a.m.-2:48 p.m.
1 stop4h 14m
Toronto Pearson Intl
Tue 25/11
12:08 p.m.-6:08 p.m.
1 stop7h 00m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Sat 22/11
6:48 p.m.-11:05 p.m.
1 stop3h 17m
Toronto Pearson Intl
Tue 25/11
9:52 a.m.-12:34 p.m.
1 stop3h 42m
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Fri 5/12
6:40 p.m.-11:11 p.m.
1 stop3h 31m
Toronto Pearson Intl
Mon 8/12
6:05 a.m.-12:34 p.m.
1 stop7h 29m
Best time to book a flight from Midway
Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Travel insights for flights from Midway
Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Chicago Midway Airport?
Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport (average of C$ 189). Flying from Chicago Midway Airport in March will prove the most costly (average of C$ 662). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
What are popular destinations to fly to from Chicago Midway Airport?
From Chicago Midway Airport you can expect to find greater availability for the following destinations: Detroit (160 flights per day), Atlanta (131 flights per day) and Orlando (108 flights per day).
What is the cheapest place to fly to from Chicago Midway Airport?
The cheapest city to fly to from Chicago Midway Airport is New York, with prices starting at C$ 110. Explore other affordable destinations below.
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Alternate flight departure points to Midway
Consider leaving from one of these other departure points that are located a short distance from Midway. Flight origins were last updated on 23 October 2025.
Related info for your journey
Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 23 October 2025.
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