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Cheap flights from Pearson Intl (YYZ) to Midway (MDW) from $156

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 8/27. 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.
YYZ — MDW
jun. 11 — jun. 181
From?
To?
mar. 6/11
mar. 6/18
1 adult, Economy
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Cheap flight deals from Pearson Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated junio 6, 2024.

Popular in

August

Cheapest in

February

Round-trip from

$223

One-way from

$214
High demand for flights, 19% potential price rise
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Best time to find cheap flights, 39% potential price drop
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From Toronto Pearson Intl to Chicago Midway
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One-way flight from Toronto Pearson Intl to Chicago Midway
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What is the cheapest day to fly round-trip from Toronto Pearson Intl Airport to Chicago Midway Airport?

Flights from Toronto Pearson Intl Airport to Chicago Midway Airport are found to be more expensive on Wednesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway Airport.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

Find a great deal and save up to 90% by booking at least 38 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Toronto Pearson Intl Airport to Chicago Midway Airport within the next two weeks, with the cheapest ticket starting at $337.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

Due to multiple factors, expect to potentially pay more when booking in August. For low rates, April can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Toronto Pearson Intl Airport in April are about $290 on average during April, but can be found for as low as $193.

What is the cheapest time of day to fly from YYZ to MDW?

One of the essential ways to save on airfare from Toronto Pearson Intl Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 28% on airfare.

Cheap Pearson Intl to Midway flights in June & July 2024

Find cheap flight options from Pearson Intl to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on junio 6, 2024.
Check out some of the best flight deals from Toronto to Chicago in 2024. Check back soon for alternative fares.
mié. 7/1712:30 pmYYZ - MDW
1 stop7h 09mDelta
sáb. 7/205:43 pmMDW - YYZ
1 stop4h 10mDelta
Deal found 6/5$279
sáb. 6/2912:30 pmYYZ - MDW
1 stop5h 34mDelta
lun. 7/19:29 amMDW - YYZ
1 stop6h 39mDelta
Deal found 6/4$298
sáb. 6/2912:30 pmYYZ - MDW
1 stop5h 34mDelta
mié. 7/39:34 amMDW - YYZ
1 stop6h 34mDelta
Deal found 6/5$305
mié. 7/36:30 amYYZ - MDW
1 stop8h 14mDelta
sáb. 7/69:29 amMDW - YYZ
1 stop6h 39mDelta
Deal found 6/5$313
jue. 7/259:45 amYYZ - MDW
1 stop8h 18mDelta
lun. 7/291:25 pmMDW - YYZ
1 stop8h 28mDelta
Deal found 6/5$324
sáb. 6/226:30 amYYZ - MDW
1 stop5h 57mDelta
mié. 6/269:29 amMDW - YYZ
1 stop8h 04mDelta
Deal found 6/6$325
jue. 6/138:00 pmYYZ - MDW
1 stop10h 14mMultiple Airlines
mar. 6/187:54 pmMDW - YYZ
1 stop9h 51mMultiple Airlines
Deal found 6/4$342
vie. 7/51:25 pmYYZ - MDW
1 stop21h 26mWestJet
vie. 7/127:19 pmMDW - YYZ
1 stop15h 20mWestJet
Deal found 6/5$351
sáb. 7/136:30 amYYZ - MDW
1 stop13h 09mWestJet
mar. 7/162:49 pmMDW - YYZ
1 stop7h 23mWestJet
Deal found 6/6$361

Pearson Intl to Midway 2024 flight deals

Discover exclusive flight deals for travel between Pearson Intl and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.
Check out some of the best flight deals from Toronto to Chicago in 2024. Check back soon for alternative fares.
mié. 8/2112:30 pmYYZ - MDW
1 stop7h 08mDelta
sáb. 8/245:45 pmMDW - YYZ
1 stop4h 08mDelta
Deal found 6/5$256
mié. 7/1712:30 pmYYZ - MDW
1 stop7h 09mDelta
sáb. 7/205:43 pmMDW - YYZ
1 stop4h 10mDelta
Deal found 6/5$279
mié. 9/412:30 pmYYZ - MDW
1 stop7h 08mDelta
vie. 9/202:07 pmMDW - YYZ
1 stop8h 03mDelta
Deal found 6/5$284
sáb. 9/146:00 amYYZ - MDW
1 stop3h 40mDelta
mar. 9/179:19 amMDW - YYZ
1 stop6h 49mDelta
Deal found 6/5$287
vie. 8/3012:30 pmYYZ - MDW
1 stop5h 34mDelta
mar. 9/39:33 amMDW - YYZ
1 stop6h 35mDelta
Deal found 6/5$290
dom. 9/156:00 amYYZ - MDW
1 stop7h 28mDelta
lun. 9/165:45 pmMDW - YYZ
1 stop4h 09mDelta
Deal found 6/6$294
sáb. 10/512:20 pmYYZ - MDW
1 stop5h 44mDelta
mié. 10/99:35 amMDW - YYZ
1 stop6h 34mDelta
Deal found 6/5$295
vie. 8/166:04 amYYZ - MDW
1 stop7h 38mDelta
lun. 8/191:24 pmMDW - YYZ
1 stop8h 29mDelta
Deal found 6/5$298
sáb. 6/2912:30 pmYYZ - MDW
1 stop5h 34mDelta
mié. 7/39:34 amMDW - YYZ
1 stop6h 34mDelta
Deal found 6/5$305

Pearson Intl to Midway flights leaving soon

Find last-minute flight options from Pearson Intl to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.
Check out these flights departing soon from Toronto to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
jue. 6/138:00 pmYYZ - MDW
1 stop10h 14mMultiple Airlines
mar. 6/187:54 pmMDW - YYZ
1 stop9h 51mMultiple Airlines
Deal found 6/4$342
dom. 6/166:04 amYYZ - MDW
1 stop3h 44mDelta
mar. 6/182:24 pmMDW - YYZ
1 stop7h 48mDelta
Deal found 6/5$373
mar. 6/1112:30 pmYYZ - MDW
1 stop5h 34mDelta
dom. 6/169:34 amMDW - YYZ
1 stop6h 34mDelta
Deal found 6/4$384
mié. 6/128:00 pmYYZ - MDW
1 stop10h 29mMultiple Airlines
sáb. 6/1511:51 amMDW - YYZ
1 stop10h 35mMultiple Airlines
Deal found 6/4$386
vie. 6/1412:31 pmYYZ - MDW
1 stop7h 05mDelta
dom. 6/169:34 amMDW - YYZ
1 stop6h 34mDelta
Deal found 6/6$394
mar. 6/1112:30 pmYYZ - MDW
1 stop5h 34mDelta
jue. 6/139:34 amMDW - YYZ
1 stop6h 34mDelta
Deal found 6/4$395
jue. 6/1310:15 pmYYZ - MDW
2 stops32h 14mMultiple Airlines
mar. 6/187:54 pmMDW - YYZ
1 stop22h 56mMultiple Airlines
Deal found 6/4$403
jue. 6/138:00 pmYYZ - MDW
1 stop10h 14mMultiple Airlines
sáb. 6/1511:51 amMDW - YYZ
1 stop10h 35mMultiple Airlines
Deal found 6/4$404
dom. 6/167:46 amYYZ - MDW
1 stop8h 09mWestJet
jue. 6/209:29 amMDW - YYZ
1 stop8h 04mWestJet
Deal found 6/5$407

One-way flights to Midway from Pearson Intl

Search for one-way flight options from Pearson Intl to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.
Some of the best available deals we've found on one-way flights from Toronto to Chicago. Those seeking round-trip flights from Toronto to Chicago should utilize the search form at the the top of the page.
mar. 8/2712:30 pmYYZ - MDW
1 stop5h 55mDelta
Deal found 6/6$156
sáb. 6/2912:30 pmYYZ - MDW
1 stop5h 34mDelta
Deal found 6/4$163
dom. 8/258:15 pmYYZ - MDW
1 stop15h 33mMultiple Airlines
Deal found 6/4$169
lun. 8/198:00 pmYYZ - MDW
1 stop11h 33mMultiple Airlines
Deal found 6/6$177
mar. 8/2012:30 pmYYZ - MDW
1 stop5h 34mDelta
Deal found 6/6$178
sáb. 6/226:30 amYYZ - MDW
1 stop5h 57mDelta
Deal found 6/5$179
vie. 8/167:00 pmYYZ - MDW
2 stops17h 44mWestJet
Deal found 6/6$184
lun. 9/97:00 pmYYZ - MDW
2 stops17h 57mWestJet
Deal found 6/5$185
mar. 7/912:30 pmYYZ - MDW
1 stop7h 09mWestJet
Deal found 6/6$189

Find flights from Pearson Intl to Midway within your budget

Customize your flight search to find flights from Pearson Intl to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$256 - $367

Route

Depart

Return

Price

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 8/21

1 stop7h 08m

Chicago Midway

sáb. 8/24

1 stop4h 08m

$256

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 7/17

1 stop7h 09m

Chicago Midway

sáb. 7/20

1 stop4h 10m

$279

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 9/4

1 stop7h 08m

Chicago Midway

vie. 9/20

1 stop8h 03m

$284

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 9/14

1 stop5h 44m

Chicago Midway

mié. 9/18

1 stop6h 49m

$287

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 10/19

1 stop6h 35m

Chicago Midway

mié. 10/23

1 stop6h 34m

$323

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 8/14

1 stop9h 21m

Chicago Midway

sáb. 8/17

1 stop10h 22m

$340

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

dom. 9/1

1 stop7h 08m

Chicago Midway

mié. 9/4

1 stop10h 22m

$341

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 8/16

1 stop25h 09m

Chicago Midway

mar. 8/20

1 stop8h 23m

$342

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mar. 6/18

1 stop17h 13m

Chicago Midway

dom. 6/23

1 stop25h 09m

$367

Flights are sorted by cheapest first

Deals found on 6/5

What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to Midway. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago Midway Airport flight should consider departing on Thursday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Pearson Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pearson Intl 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.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated junio 6, 2024.
See what other customers who have flown with WestJet and Delta from Toronto to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

KLM
7.9
Good
1,489 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,856 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Pearson Intl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Toronto Pearson Intl Airport to Chicago Midway Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from Toronto Pearson Intl Airport to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Delta for just $256, but on average you can expect to pay $315.

  • Are there last-minute flights available from Toronto Pearson Intl Airport to Chicago Midway Airport for under $400?

    There are currently 20+ open flights from Toronto Pearson Intl Airport to Chicago Midway Airport within the next 7 days for less than $400.

  • What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago Midway Airport round-trip?

    Delta, at $256, was found to be the cheapest airline from Toronto Pearson Intl Airport to Chicago Midway Airport.Alternate airlines to your destination round-trip include KLM and WestJet. Delta is 36% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $156. However, be on the lookout for offers from WestJet and KLM, as they are both options that can get you from Toronto Pearson Intl Airport to Chicago Midway Airport for a low price.

  • What does YYZ to MDW mean?

    YYZ stands for Toronto Pearson Intl Airport, while MDW stands for Chicago Midway Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry.

  • Can I find deals for flights from Pearson Intl to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Pearson Intl to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Pearson Intl to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Pearson Intl to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Pearson Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Midway.

  • Can I find deals for business class flights from Pearson Intl to Midway?

    Yes. Cheapflights offers flight deals from Pearson Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Pearson Intl to Midway that allow pets onboard?

    Many airlines flying from Pearson Intl to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Pearson Intl to Midway?

    Yes, you can often find last-minute deals on Pearson Intl to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Toronto Pearson Intl Airport to Chicago Midway Airport flight deals updated?

    The Toronto Pearson Intl Airport to Chicago Midway Airport flight deals you see on this page were last updated on 6/6.

  • What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $141). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in July is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Pearson Intl to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Search flights from Pearson Intl to Midway by cabin class

Find flights from Pearson Intl to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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