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C$ 112+ 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 9/4. 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 — YUL
25 Feb — 4 Mar1
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 20 February 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 382 or less

Good one-way deal

C$ 62 or less
On average, Frontier currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 122).
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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 20 February 2025.

Sat 5/412:55 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 12/411:10 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 19/2C$ 300
Sat 12/47:39 a.m.MDW - YVR
2 stops16h 51mMultiple Airlines
Tue 15/49:05 a.m.YVR - MDW
1 stop18h 18mMultiple Airlines
Deal found 19/2C$ 315
Wed 16/411:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Wed 23/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 19/2C$ 315
Sun 6/45:15 a.m.MDW - YYZ
1 stop17h 15mMultiple Airlines
Sun 13/47:25 p.m.YYZ - MDW
1 stop10h 55mMultiple Airlines
Deal found 20/2C$ 351
Tue 1/41:16 p.m.MDW - YYC
1 stop8h 26mDelta
Tue 8/46:30 a.m.YYC - MDW
1 stop6h 47mDelta
Deal found 19/2C$ 355
Fri 25/45:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Sun 27/43:50 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 19/2C$ 357
Thu 3/45:35 p.m.MDW - YUL
1 stop4h 12mPorter Airlines
Sun 6/46:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Deal found 19/2C$ 382
Thu 10/46:27 p.m.MDW - YEG
1 stop18h 33mMultiple Airlines
Tue 15/46:40 a.m.YEG - MDW
1 stop8h 01mMultiple Airlines
Deal found 19/2C$ 396
Tue 1/46:42 p.m.MDW - YYZ
1 stop2h 56mDelta
Tue 8/46:30 a.m.YYZ - MDW
1 stop8h 47mDelta
Deal found 20/2C$ 422
Thu 10/48:50 p.m.MDW - YYC
1 stop16h 48mMultiple Airlines
Tue 15/49:55 a.m.YYC - MDW
1 stop8h 50mMultiple Airlines
Deal found 18/2C$ 425
Sat 5/412:55 p.m.MDW - YHZ
1 stop5h 50mPorter Airlines
Sat 12/48:30 a.m.YHZ - MDW
1 stop5h 30mPorter Airlines
Deal found 19/2C$ 429
Tue 4/38:30 a.m.MDW - YOW
1 stop7h 42mMultiple Airlines
Wed 5/34:25 p.m.YOW - MDW
1 stop7h 35mMultiple Airlines
Deal found 19/2C$ 459

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 20 February 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pierre Elliott Trudeau Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 5/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

Toronto Island

Sat 12/4

11:10 a.m.-12:00 p.m.

Nonstop1h 50m

C$ 300

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Sat 12/4

7:39 a.m.-10:30 p.m.

2 stops16h 51m

Vancouver Intl

Tue 15/4

9:05 a.m.-5:23 a.m.

1 stop18h 18m

C$ 315

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 16/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

Toronto Island

Wed 23/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

C$ 315

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 6/4

5:15 a.m.-11:30 p.m.

1 stop17h 15m

Toronto Pearson Intl

Sun 13/4

7:25 p.m.-5:20 a.m.

1 stop10h 55m

C$ 351

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 1/4

1:16 p.m.-8:42 p.m.

1 stop8h 26m

Calgary

Tue 8/4

6:30 a.m.-2:17 p.m.

1 stop6h 47m

C$ 355

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 25/4

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 27/4

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

C$ 357

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 3/4

5:35 p.m.-10:47 p.m.

1 stop4h 12m

Montreal Pierre Elliott Trudeau Intl

Sun 6/4

6:50 a.m.-10:20 a.m.

1 stop4h 30m

C$ 382

ChicagoEdmonton

MDW - YEG

MDWYEG

Chicago Midway

Thu 10/4

6:27 p.m.-12:00 p.m.

1 stop18h 33m

Edmonton

Tue 15/4

6:40 a.m.-3:41 p.m.

1 stop8h 01m

C$ 396

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 1/4

2:55 p.m.-7:07 p.m.

1 stop3h 12m

Toronto Pearson Intl

Tue 8/4

1:20 p.m.-6:02 p.m.

1 stop5h 42m

C$ 422

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 10/4

8:50 p.m.-12:38 p.m.

1 stop16h 48m

Calgary

Tue 15/4

9:55 a.m.-7:45 p.m.

1 stop8h 50m

C$ 425

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/2

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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 (164 flights per day), Atlanta (162 flights per day) and Orlando (144 flights per day).

Toronto

Toronto

From C$ 107

Miami

Miami

From C$ 39

Phoenix Sky Harbor Intl

Phoenix Sky Harbor Intl

From C$ 250

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 Miami, with prices starting at C$ 55. Explore other affordable destinations below.

Miami

Miami

From C$ 39

Toronto

Toronto

From C$ 107

Phoenix Sky Harbor Intl

Phoenix Sky Harbor Intl

From C$ 250

Zacatecas La Calera

Zacatecas La Calera

From C$ 361

Airline reviews for flights from Midway

Get insights into the airlines that provide service from Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Midway. In the last 7 days, Cheapflights users made a total of 629,999 searches.
Delta
8.0
Very good
8,227 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,227 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.2
Good
2,802 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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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 20 February 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 20 February 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, Miami. Throughout the year, Las Vegas, Atlanta, Orlando Airport 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$ 55 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 470 to fly from Chicago Midway Airport.

  • What is the cheapest premium economy flight from Chicago Midway Airport?

    Options for some of the cheapest premium economy flights from Chicago Midway Airport we have found on Cheapflights are as follows:
    Fly from Chicago Midway to Detroit Metropolitan Wayne County Airport starting at C$ 489

  • 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$ 297 round trip
    Travel from Chicago to Vancouver from C$ 315 round trip
    Travel from Chicago to Calgary from C$ 348 round trip
    Travel from Chicago to Montreal from C$ 382 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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