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C$ 109+ 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 3/8. 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
17 Jun — 24 Jun1
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 12 June 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 263 or less

Good one-way deal

C$ 111 or less
On average, Frontier currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 221).
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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 12 June 2025.

Thu 18/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 20/97:30 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 12/6C$ 231
Tue 24/69:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 12/6C$ 269
Wed 13/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Sat 16/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 11/6C$ 295
Tue 23/95:59 p.m.MDW - YYZ
1 stop3h 59mDelta
Sat 27/96:00 a.m.YYZ - MDW
1 stop3h 45mDelta
Deal found 11/6C$ 320
Fri 18/75:20 p.m.MDW - YTZ
Nonstop1h 42mAPG Airlines
Sun 20/77:55 a.m.YTZ - MDW
Nonstop1h 50mAPG Airlines
Deal found 11/6C$ 331
Tue 12/89:15 a.m.MDW - YYC
1 stop5h 18mDelta
Fri 22/86:40 a.m.YYC - MDW
1 stop9h 57mDelta
Deal found 10/6C$ 343
Thu 24/79:40 a.m.MDW - YOW
1 stop8h 13mPorter Airlines
Tue 29/79:35 a.m.YOW - MDW
1 stop7h 49mPorter Airlines
Deal found 12/6C$ 349
Fri 11/75:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Mon 14/710:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Deal found 11/6C$ 371
Wed 23/711:39 a.m.MDW - YVR
2 stops12h 11mMultiple Airlines
Tue 16/912:15 p.m.YVR - MDW
1 stop8h 43mMultiple Airlines
Deal found 11/6C$ 405
Sat 6/99:15 a.m.MDW - YEG
1 stop7h 44mDelta
Mon 15/99:35 a.m.YEG - MDW
1 stop11h 09mDelta
Deal found 10/6C$ 416
Sat 13/96:10 a.m.MDW - YYC
1 stop14h 50mMultiple Airlines
Wed 17/97:00 a.m.YYC - MDW
2 stops14h 58mMultiple Airlines
Deal found 11/6C$ 418
Wed 30/79:40 a.m.MDW - YUL
1 stop13h 57mMultiple Airlines
Tue 5/810:45 a.m.YUL - MDW
1 stop6h 39mMultiple Airlines
Deal found 11/6C$ 432

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 12 June 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

Thu 18/9

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

Nonstop1h 42m

Toronto Island

Sat 20/9

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

Nonstop1h 49m

C$ 231

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 24/6

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

Nonstop1h 42m

Toronto Island

Thu 26/6

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

Nonstop1h 50m

C$ 269

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 13/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

Toronto Island

Sat 16/8

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

Nonstop1h 50m

C$ 295

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 23/9

5:59 p.m.-10:58 p.m.

1 stop3h 59m

Toronto Pearson Intl

Sat 27/9

6:00 a.m.-8:45 a.m.

1 stop3h 45m

C$ 320

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 18/7

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

Nonstop1h 42m

Toronto Island

Sun 20/7

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

Nonstop1h 50m

C$ 331

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 12/8

9:15 a.m.-1:33 p.m.

1 stop5h 18m

Calgary

Fri 22/8

6:40 a.m.-5:37 p.m.

1 stop9h 57m

C$ 343

ChicagoOttawa

MDW - YOW

MDWYOW

Chicago Midway

Thu 24/7

9:40 a.m.-6:53 p.m.

1 stop8h 13m

Ottawa

Tue 29/7

9:35 a.m.-4:24 p.m.

1 stop7h 49m

C$ 349

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 11/7

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

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Mon 14/7

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

1 stop6h 39m

C$ 371

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Wed 23/7

11:39 a.m.-9:50 p.m.

2 stops12h 11m

Vancouver Intl

Tue 16/9

12:15 p.m.-10:58 p.m.

1 stop8h 43m

C$ 405

ChicagoEdmonton

MDW - YEG

MDWYEG

Chicago Midway

Sat 6/9

9:15 a.m.-3:59 p.m.

1 stop7h 44m

Edmonton

Mon 15/9

9:35 a.m.-9:44 p.m.

1 stop11h 09m

C$ 416

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 (216 flights per day), Atlanta (179 flights per day) and Minneapolis (110 flights per day).

Toronto
Toronto
From C$ 68
Miami
Miami
From C$ 146
Fort Lauderdale
Fort Lauderdale
From C$ 226
Phoenix Sky Harbor Intl
Phoenix Sky Harbor Intl
From C$ 250

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
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 109
Miami
Miami
From C$ 146
Fort Lauderdale
Fort Lauderdale
From C$ 226

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
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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
396 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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 12 June 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 12 June 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 Cancún, 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$ 92 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 385 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$ 231 round trip
    Travel from Chicago to Montreal from C$ 310 round trip
    Travel from Chicago to Calgary from C$ 343 round trip
    Travel from Chicago to Vancouver from C$ 346 round trip
    Travel from Chicago to Edmonton from C$ 387 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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