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C$ 139+ 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 7/5. 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 — YVR
20 Apr — 27 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 15 April 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 303 or less

Good one-way deal

C$ 186 or less
On average, Frontier currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 121).
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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 15 April 2025.

Sun 18/59:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 23/57:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 13/4C$ 265
Tue 13/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Sat 24/57:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 14/4C$ 304
Tue 27/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Wed 28/51:10 p.m.YUL - MDW
1 stop4h 44mPorter Airlines
Deal found 14/4C$ 309
Fri 20/69:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Sun 22/67:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 14/4C$ 336
Mon 26/59:40 a.m.MDW - YOW
1 stop5h 53mPorter Airlines
Fri 30/512:35 p.m.YOW - MDW
1 stop5h 19mPorter Airlines
Deal found 14/4C$ 340
Sat 3/51:16 p.m.MDW - YYC
1 stop8h 31mDelta
Tue 6/56:45 a.m.YYC - MDW
1 stop9h 34mDelta
Deal found 14/4C$ 347
Fri 30/59:20 a.m.MDW - YYZ
1 stop8h 11mDelta
Fri 6/63:50 p.m.YYZ - MDW
1 stop3h 55mDelta
Deal found 15/4C$ 373
Fri 9/59:40 a.m.MDW - YUL
1 stop13h 57mMultiple Airlines
Mon 12/51:10 p.m.YUL - MDW
1 stop4h 44mMultiple Airlines
Deal found 14/4C$ 404
Fri 9/56:25 p.m.MDW - YUL
1 stop3h 51mDelta
Sun 11/56:00 a.m.YUL - MDW
1 stop3h 40mDelta
Deal found 14/4C$ 413
Sat 7/69:59 a.m.MDW - YVR
2 stops14h 26mMultiple Airlines
Fri 13/69:30 a.m.YVR - MDW
1 stop11h 48mMultiple Airlines
Deal found 14/4C$ 423
Mon 5/59:40 a.m.MDW - YHZ
2 stops11h 34mPorter Airlines
Wed 7/59:15 a.m.YHZ - MDW
2 stops9h 39mPorter Airlines
Deal found 14/4C$ 427
Thu 1/58:03 p.m.MDW - YYC
1 stop19h 42mMultiple Airlines
Fri 2/512:30 a.m.YYC - MDW
1 stop8h 03mMultiple Airlines
Deal found 13/4C$ 430

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

Fly to

Vancouver Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 18/5

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

Nonstop1h 42m

Toronto Island

Fri 23/5

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

Nonstop1h 50m

C$ 265

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 13/5

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

Nonstop1h 42m

Toronto Island

Sat 24/5

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

Nonstop1h 50m

C$ 304

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 27/5

9:40 a.m.-4:00 p.m.

1 stop5h 20m

Montreal Pierre Elliott Trudeau Intl

Wed 28/5

1:10 p.m.-4:54 p.m.

1 stop4h 44m

C$ 309

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 20/6

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

Nonstop1h 40m

Toronto Island

Sun 22/6

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

Nonstop1h 50m

C$ 336

ChicagoOttawa

MDW - YOW

MDWYOW

Chicago Midway

Mon 26/5

9:40 a.m.-4:33 p.m.

1 stop5h 53m

Ottawa

Fri 30/5

12:35 p.m.-4:54 p.m.

1 stop5h 19m

C$ 340

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 3/5

1:16 p.m.-8:47 p.m.

1 stop8h 31m

Calgary

Tue 6/5

6:45 a.m.-5:19 p.m.

1 stop9h 34m

C$ 347

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 30/5

9:20 a.m.-6:31 p.m.

1 stop8h 11m

Toronto Pearson Intl

Fri 6/6

3:50 p.m.-6:45 p.m.

1 stop3h 55m

C$ 373

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 9/5

9:40 a.m.-12:37 a.m.

1 stop13h 57m

Montreal Pierre Elliott Trudeau Intl

Mon 12/5

1:10 p.m.-4:54 p.m.

1 stop4h 44m

C$ 404

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 9/5

6:25 p.m.-11:16 p.m.

1 stop3h 51m

Montreal Pierre Elliott Trudeau Intl

Sun 11/5

6:00 a.m.-8:40 a.m.

1 stop3h 40m

C$ 413

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Sat 7/6

9:59 a.m.-10:25 p.m.

2 stops14h 26m

Vancouver Intl

Fri 13/6

9:30 a.m.-11:18 p.m.

1 stop11h 48m

C$ 423

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/4

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: Atlanta (140 flights per day), Orlando (108 flights per day) and Detroit (84 flights per day).

Toronto

Toronto

From C$ 83

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$ 115. Explore other affordable destinations below.

Toronto

Toronto

From C$ 83

Miami

Miami

From C$ 146

Fort Lauderdale

Fort Lauderdale

From C$ 226

Phoenix Sky Harbor Intl

Phoenix Sky Harbor Intl

From C$ 250

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
280 reviews
Check prices

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.7

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
8.0
Very good
280 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.7

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?
Delta
8.0
Very good
7,917 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.7

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?
WestJet
7.2
Good
2,805 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.7

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 15 April 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 15 April 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, 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$ 115 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 428 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$ 477

  • 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$ 258 round trip
    Travel from Chicago to Montreal from C$ 311 round trip
    Travel from Chicago to Calgary from C$ 337 round trip
    Travel from Chicago to Vancouver from C$ 433 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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