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C$ 116+ 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 17/8. 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
6 Jul — 13 Jul1
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 1 July 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 276 or less

Good one-way deal

C$ 116 or less
On average, Frontier currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 216).
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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 1 July 2025.

Fri 18/75:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Fri 25/77:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 30/6C$ 247
Thu 10/75:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 13/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 30/6C$ 250
Tue 9/95:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Sat 13/97:30 a.m.YTZ - MDW
Nonstop1h 49mAir Transat
Deal found 30/6C$ 253
Sat 6/96:17 p.m.MDW - YYZ
1 stop3h 41mDelta
Sat 13/912:14 p.m.YYZ - MDW
1 stop7h 21mDelta
Deal found 29/6C$ 319
Sat 13/91:43 p.m.MDW - YYC
1 stop7h 59mDelta
Sat 20/96:40 a.m.YYC - MDW
1 stop9h 55mDelta
Deal found 30/6C$ 343
Wed 15/105:20 p.m.MDW - YUL
1 stop3h 55mMultiple Airlines
Sat 18/107:00 a.m.YUL - MDW
1 stop15h 44mMultiple Airlines
Deal found 30/6C$ 370
Thu 7/85:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Mon 11/810:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Deal found 29/6C$ 373
Thu 18/96:20 a.m.MDW - YWG
1 stop10h 02mMultiple Airlines
Sat 20/96:30 a.m.YWG - MDW
2 stops16h 03mMultiple Airlines
Deal found 29/6C$ 381
Fri 15/812:43 p.m.MDW - YUL
1 stop10h 10mDelta
Fri 22/812:55 p.m.YUL - MDW
1 stop6h 42mDelta
Deal found 30/6C$ 382
Mon 25/810:58 a.m.MDW - YYC
1 stop10h 02mMultiple Airlines
Tue 2/912:30 a.m.YYC - MDW
1 stop12h 31mMultiple Airlines
Deal found 30/6C$ 407
Tue 5/89:24 a.m.MDW - YYZ
1 stop8h 10mWestJet
Wed 6/81:20 p.m.YYZ - MDW
1 stop9h 22mWestJet
Deal found 30/6C$ 415
Wed 10/99:00 a.m.MDW - YEG
2 stops14h 27mMultiple Airlines
Sun 14/99:35 a.m.YEG - MDW
1 stop12h 45mMultiple Airlines
Deal found 30/6C$ 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 1 July 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 18/7

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

Nonstop1h 42m

Toronto Island

Fri 25/7

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

Nonstop1h 50m

C$ 247

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/7

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

Nonstop1h 42m

Toronto Island

Sat 12/7

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

Nonstop1h 50m

C$ 250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 9/9

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

Nonstop1h 42m

Toronto Island

Sat 13/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

C$ 253

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 6/9

6:17 p.m.-10:58 p.m.

1 stop3h 41m

Toronto Pearson Intl

Sat 13/9

12:14 p.m.-6:35 p.m.

1 stop7h 21m

C$ 319

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 13/9

1:43 p.m.-8:42 p.m.

1 stop7h 59m

Calgary

Sat 20/9

6:40 a.m.-5:35 p.m.

1 stop9h 55m

C$ 343

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 15/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Sat 18/10

7:00 a.m.-9:44 p.m.

1 stop15h 44m

C$ 370

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 7/8

5:20 p.m.-10:15 p.m.

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Mon 11/8

10:45 a.m.-4:24 p.m.

1 stop6h 39m

C$ 373

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 18/9

6:20 a.m.-4:22 p.m.

1 stop10h 02m

Winnipeg

Sat 20/9

6:30 a.m.-10:33 p.m.

2 stops16h 03m

C$ 381

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 15/8

12:43 p.m.-11:53 p.m.

1 stop10h 10m

Montreal Pierre Elliott Trudeau Intl

Fri 22/8

12:55 p.m.-6:37 p.m.

1 stop6h 42m

C$ 382

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 25/8

10:58 a.m.-8:00 p.m.

1 stop10h 02m

Calgary

Tue 2/9

12:30 a.m.-2:01 p.m.

1 stop12h 31m

C$ 407

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/6

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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: Atlanta (173 flights per day), Detroit (162 flights per day) and Orlando (104 flights per day).

Toronto
Toronto
From C$ 68
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$ 92. Explore other affordable destinations below.

Toronto
Toronto
From C$ 68
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.
Check out reviews from past customers who have flown Porter Airlines and Air Transat from Chicago Midway Airport to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
296 reviews
Check prices

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
296 reviews
Porter Airlines
8.0
Very good
296 reviews
Check prices

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
405 reviews
Porter Airlines
8.0
Very good
296 reviews
Check prices

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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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 1 July 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 1 July 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 Punta Cana, Las Vegas, Atlanta. 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$ 92 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 473 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$ 470

  • 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$ 263 round trip
    Travel from Chicago to Montreal from C$ 303 round trip
    Travel from Chicago to Calgary from C$ 344 round trip
    Travel from Chicago to Vancouver from C$ 420 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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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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