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C$ 70+ 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 19/9. 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.
MDW — YTZ
19 Aug — 26 Aug1
1 adult

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 14 August 2025.

Cheapest airline

Air Canada

Good round-trip deal

C$ 241 or less

Good one-way deal

C$ 107 or less
On average, Air Canada currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 494).
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Price to beat on a round-trip flight from Chicago Midway.
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

Cheapest flights from Midway
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 14 August 2025.

Fri 12/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Mon 15/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 12/8C$ 195
Sat 13/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Mon 15/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 13/8C$ 211
Thu 2/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Sun 5/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 12/8C$ 223
Wed 3/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Thu 4/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 12/8C$ 227
Sat 4/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Mon 6/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 12/8C$ 230
Fri 5/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Mon 8/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 12/8C$ 235
Wed 3/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 6/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 13/8C$ 263
Wed 3/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 7/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 13/8C$ 264
Wed 3/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 3/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 13/8C$ 266
Thu 4/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 9/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 12/8C$ 268
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 13/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 12/8C$ 270
Thu 2/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 11/8C$ 271

Find flights from Midway within your budget

 
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 14 August 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Toronto Island

Route

Depart

Return

Price

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Fri 12/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Mon 15/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 195

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sat 13/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Mon 15/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 198

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Thu 2/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Sun 5/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 223

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Fri 5/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Mon 8/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 227

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Wed 3/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Thu 4/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 227

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sat 4/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Mon 6/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 230

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Thu 25/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

Québec City

Sun 28/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

C$ 235

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 17/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 19/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 15/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Mon 22/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 14/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 60 results
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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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

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 (230 flights per day), Atlanta (171 flights per day) and Orlando (92 flights per day).

Toronto
Toronto
From C$ 56
Zacatecas La Calera
Zacatecas La Calera
From C$ 361

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Toronto, with prices starting at C$ 77. Explore other affordable destinations below.

Toronto
Toronto
From C$ 56
Zacatecas La Calera
Zacatecas La Calera
From C$ 361

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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 14 August 2025.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Evansville
Flights from Belleville
Flights from Bloomington
Flights from Peoria
Flights from Champaign
Flights from Moline
Flights from Dubuque
Flights from Springfield

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 14 August 2025.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    This month, the top selected destinations from Chicago Midway Airport are Atlanta, Las Vegas, Orlando Airport. Throughout the year, Atlanta, Las Vegas, Cancún are some of the top choices made by users flying from Chicago Midway Airport.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as C$ 77 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 437 to fly from Chicago Midway Airport.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    Check out the cheapest flights from Chicago Midway Airport to embark to:
    Travel from Chicago to Toronto from C$ 241 round trip
    Travel from Chicago to Montreal from C$ 304 round trip
    Travel from Chicago to Vancouver from C$ 312 round trip
    Travel from Chicago to Calgary from C$ 346 round trip

  • How does Cheapflights help users find flights from Midway?

    Deals for flights from Midway are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

  • Why should you use Cheapflights to find cheap flight tickets from Midway?

    Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Midway with no change fees?

    Yes! Cheapflights helps users easily find flights from Midway with no change fees.

  • Can Cheapflights notify me if prices for flights from Midway become cheaper?

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway?

Deals for flights from Midway are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Midway?

Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Midway with no change fees.

Can Cheapflights notify me if prices for flights from Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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