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C$ 96+ 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 15/10. 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
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Cheapest airline

Air Canada

Good round-trip deal

C$ 220 or less

Good one-way deal

C$ 108 or less
On average, Air Canada currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 487).
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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 17 September 2025.

Sat 18/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Thu 23/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 15/9C$ 235
Mon 20/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Thu 23/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 15/9C$ 238
Mon 6/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Fri 17/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Deal found 16/9C$ 241
Wed 12/112:06 p.m.MDW - YVR
1 stop23h 06mMultiple Airlines
Tue 18/117:45 p.m.YVR - MDW
2 stops14h 56mMultiple Airlines
Deal found 15/9C$ 279
Wed 15/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Wed 22/108:30 p.m.YVR - MDW
2 stops21h 51mMultiple Airlines
Deal found 15/9C$ 283
Tue 25/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Mon 1/128:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Deal found 16/9C$ 286
Sat 4/106:15 a.m.MDW - YVR
1 stop16h 33mMultiple Airlines
Tue 7/109:30 a.m.YVR - MDW
1 stop26h 08mMultiple Airlines
Deal found 15/9C$ 290
Thu 30/1011:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Thu 6/118:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Deal found 15/9C$ 303
Sat 4/109:35 a.m.MDW - YHZ
2 stops12h 05mPorter Airlines
Wed 8/106:10 a.m.YHZ - MDW
2 stops12h 14mPorter Airlines
Deal found 14/9C$ 308
Wed 15/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Wed 22/1012:00 p.m.YTZ - MDW
2 stops22h 47mMultiple Airlines
Deal found 17/9C$ 316
Sat 11/109:35 a.m.MDW - YHZ
2 stops12h 05mPorter Airlines
Thu 16/106:10 a.m.YHZ - MDW
2 stops12h 14mPorter Airlines
Deal found 16/9C$ 319
Thu 6/116:25 a.m.MDW - YVR
2 stops19h 50mMultiple Airlines
Sun 9/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Deal found 15/9C$ 325

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 17 September 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

Sun 19/10

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

1 stop5h 20m

Québec City

Thu 23/10

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

1 stop6h 24m

C$ 235

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Mon 6/10

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

1 stop5h 20m

Québec City

Fri 17/10

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

1 stop6h 24m

C$ 241

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sun 12/10

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

1 stop5h 20m

Québec City

Thu 16/10

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

1 stop6h 24m

C$ 243

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Sat 11/10

9:35 a.m.-11:40 p.m.

2 stops12h 05m

Halifax Intl

Thu 16/10

6:10 a.m.-4:24 p.m.

2 stops12h 14m

C$ 319

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sun 19/10

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

1 stop5h 20m

Québec City

Fri 24/10

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

1 stop6h 24m

C$ 327

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Wed 26/11

11:00 a.m.-8:05 p.m.

1 stop7h 05m

Halifax Intl

Mon 1/12

8:30 a.m.-3:20 p.m.

1 stop8h 50m

C$ 329

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Thu 30/10

11:00 a.m.-7:51 p.m.

2 stops6h 51m

Halifax Intl

Thu 6/11

8:25 a.m.-3:20 p.m.

2 stops8h 55m

C$ 332

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Tue 30/12

11:00 a.m.-11:54 p.m.

2 stops10h 54m

Halifax Intl

Mon 5/1

8:30 a.m.-3:20 p.m.

1 stop8h 50m

C$ 336

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Tue 14/10

8:05 a.m.-8:48 p.m.

1 stop14h 43m

Vancouver Intl

Tue 21/10

9:30 a.m.-1:38 p.m.

1 stop26h 08m

C$ 338

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/10

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

Nonstop1h 42m

Toronto Island

Wed 22/10

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

Nonstop1h 49m

C$ 344

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

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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 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$ 186). Flying from Chicago Midway Airport in March will prove the most costly (average of C$ 651). 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 (204 flights per day), Atlanta (175 flights per day) and Minneapolis (109 flights per day).

Toronto
Toronto
From C$ 57
Zacatecas La Calera
Zacatecas La Calera
From C$ 361
Buffalo
Buffalo
From C$ 88
New York
New York
From C$ 78

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$ 79. Explore other affordable destinations below.

Toronto
Toronto
From C$ 57
New York
New York
From C$ 78
Buffalo
Buffalo
From C$ 88
Zacatecas La Calera
Zacatecas La Calera
From C$ 361

Browse thousands of different options on Cheapflights for your next trip

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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 17 September 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 17 September 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 Las Vegas, Atlanta, 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$ 79 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 318 to fly from Chicago Midway Airport.

  • What is the cheapest month to fly from Chicago Midway Airport?

    At the present moment the cheapest month to fly from Chicago Midway Airport is currently August; with March being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • 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$ 319 round trip
    Travel from Chicago to Calgary from C$ 321 round trip
    Travel from Chicago to Vancouver from C$ 325 round trip
    Travel from Chicago to Montreal from C$ 373 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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Fly with Cheapflights

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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