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C$ 143+ 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 14/5. 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
30 Mar — 6 Apr1
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 25 March 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 313 or less

Good one-way deal

C$ 258 or less
On average, Frontier currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 125).
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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 25 March 2025.

Fri 25/411:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 27/43:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 23/3C$ 272
Tue 6/55:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 13/57:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 23/3C$ 299
Fri 25/411:15 a.m.MDW - YUL
1 stop4h 32mPorter Airlines
Tue 29/411:50 a.m.YUL - MDW
1 stop5h 50mPorter Airlines
Deal found 22/3C$ 318
Thu 8/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Thu 15/57:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 24/3C$ 345
Wed 9/41:15 p.m.MDW - YYC
1 stop8h 27mDelta
Sun 13/46:30 a.m.YYC - MDW
1 stop6h 47mDelta
Deal found 24/3C$ 358
Tue 6/59:20 a.m.MDW - YYZ
1 stop6h 58mDelta
Tue 13/59:49 a.m.YYZ - MDW
1 stop3h 39mDelta
Deal found 25/3C$ 365
Tue 13/59:34 a.m.MDW - YVR
1 stop13h 18mMultiple Airlines
Tue 20/511:00 p.m.YVR - MDW
1 stop10h 26mMultiple Airlines
Deal found 23/3C$ 397
Wed 16/76:00 a.m.MDW - YYC
1 stop15h 00mMultiple Airlines
Sat 19/78:55 a.m.YYC - MDW
1 stop10h 59mMultiple Airlines
Deal found 23/3C$ 425
Sun 4/53:02 p.m.MDW - YUL
1 stop7h 26mDelta
Sun 11/56:15 a.m.YUL - MDW
1 stop8h 00mDelta
Deal found 24/3C$ 425
Tue 15/44:40 p.m.MDW - YYZ
1 stop18h 05mMultiple Airlines
Thu 24/412:54 p.m.YYZ - MDW
1 stop5h 25mMultiple Airlines
Deal found 24/3C$ 431
Fri 18/45:35 p.m.MDW - YUL
1 stop4h 12mMultiple Airlines
Mon 21/46:00 p.m.YUL - MDW
1 stop16h 07mMultiple Airlines
Deal found 23/3C$ 433
Tue 13/59:40 a.m.MDW - YOW
1 stop7h 33mPorter Airlines
Wed 14/512:35 p.m.YOW - MDW
1 stop5h 19mPorter Airlines
Deal found 23/3C$ 438

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

Fly to

Toronto Island

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 25/4

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

Nonstop1h 42m

Toronto Island

Sun 27/4

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

Nonstop1h 50m

C$ 272

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 6/5

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Tue 13/5

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

Nonstop1h 49m

C$ 299

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 25/4

11:15 a.m.-4:47 p.m.

1 stop4h 32m

Montreal Pierre Elliott Trudeau Intl

Tue 29/4

11:50 a.m.-4:40 p.m.

1 stop5h 50m

C$ 318

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 8/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

Toronto Island

Thu 15/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

C$ 345

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 9/4

1:15 p.m.-8:42 p.m.

1 stop8h 27m

Calgary

Sun 13/4

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

1 stop6h 47m

C$ 358

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 6/5

9:20 a.m.-5:18 p.m.

1 stop6h 58m

Toronto Pearson Intl

Tue 13/5

9:49 a.m.-12:28 p.m.

1 stop3h 39m

C$ 365

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Tue 13/5

9:34 a.m.-8:52 p.m.

1 stop13h 18m

Vancouver Intl

Tue 20/5

11:00 p.m.-11:26 a.m.

1 stop10h 26m

C$ 397

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 16/7

6:00 a.m.-8:00 p.m.

1 stop15h 00m

Calgary

Sat 19/7

8:55 a.m.-8:54 p.m.

1 stop10h 59m

C$ 425

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 4/5

3:02 p.m.-11:28 p.m.

1 stop7h 26m

Montreal Pierre Elliott Trudeau Intl

Sun 11/5

6:15 a.m.-1:15 p.m.

1 stop8h 00m

C$ 425

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 15/4

4:40 p.m.-11:45 a.m.

1 stop18h 05m

Toronto Pearson Intl

Thu 24/4

12:54 p.m.-5:19 p.m.

1 stop5h 25m

C$ 431

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/3

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 is the cheapest month to book a flight from Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport (average of C$ 274). Flying from Chicago Midway Airport in January will prove the most costly (average of C$ 477). 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 (172 flights per day), Atlanta (161 flights per day) and Orlando (90 flights per day).

Toronto

Toronto

From C$ 84

Fort Lauderdale

Fort Lauderdale

From C$ 226

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 Toronto, with prices starting at C$ 120. Explore other affordable destinations below.

Toronto

Toronto

From C$ 84

Fort Lauderdale

Fort Lauderdale

From C$ 226

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.
Porter Airlines
7.9
Good
275 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

7.9

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
7.9
Good
275 reviews
Porter Airlines
7.9
Good
275 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

7.9

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Transat
7.8
Good
381 reviews
Porter Airlines
7.9
Good
275 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

7.9

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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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 25 March 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 25 March 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 Orlando Airport, Las Vegas, Atlanta. 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$ 120 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 505 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$ 493

  • 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 April; with January 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$ 265 round trip
    Travel from Chicago to Montreal from C$ 314 round trip
    Travel from Chicago to Calgary from C$ 352 round trip
    Travel from Chicago to Vancouver from C$ 365 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

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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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