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

Our cheapest airline available from Toronto Pearson Intl Airport to Chicago Midway Airport is Delta. Our recent data shows that you can find tickets from as low as C$ 333 on this airline. An additional option worth looking into is WestJet, starting at C$ 549. These flights start at 35% lower than the current average price 3 months from now.

Which airlines flying from Toronto Pearson Intl to Chicago Midway have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Toronto Pearson Intl to Chicago Midway that may be offering flexible cancellation policies are Endeavor Airlines and Porter Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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

June can be a great time to fly to Chicago Midway Airport from Toronto Pearson Intl Airport with a flight ticket averaging about C$ 348. Cheapflights users have found deals in the month of June for as cheap as C$ 222. The most expensive prices can be found in the month of March.

When is the cheapest time to fly from Toronto Pearson Intl Airport to Chicago Midway Airport (YYZ - MDW)?

When flying from Toronto Pearson Intl Airport to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What does YYZ to MDW mean?

Toronto Pearson Intl Airport is YYZ and Chicago Midway Airport is MDW. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service.

Cheap Flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 192

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

The cheapest airlines for a one-way flight from Toronto Pearson Intl Airport to Chicago Midway Airport are Delta (C$ 192), WestJet (C$ 316), and Copa Airlines (C$ 407).

Q: What are the cheapest flights from Toronto Pearson Intl Airport to Chicago Midway Airport?

The cheapest flight price from Toronto Pearson Intl Airport to Chicago Midway Airport is C$ 267. On average you can expect to pay C$ 976. The most popular route, (Toronto Pearson Intl - Chicago Midway), can usually be booked for C$ 314.

Q: Can I find flights from Toronto Pearson Intl Airport to Chicago Midway Airport for under C$ 400 on Cheapflights?

Yes, there are multiple flights from Toronto Pearson Intl Airport to Chicago Midway Airport for under C$ 400. The cheapest flight booked recently is on Delta for just C$ 333, but on average you can expect to pay C$ 455.

Q: Are there last-minute flights available from Toronto Pearson Intl Airport to Chicago Midway Airport for under C$ 600?

There are currently 10+ open flights from Toronto Pearson Intl Airport to Chicago Midway Airport within the next 7 days for less than C$ 600.

How to find the cheapest flight from Pearson Intl (YYZ) to Midway (MDW)

YYZ - MDW Price	C$ 278 - C$ 493
MDW Temperature	-5 - 23 °C
MDW Rainfall	43 - 125 mm

YYZ - MDW

Price

C$ 278 - C$ 493

MDW

Temperature

-5 - 23 °C

MDW

Rainfall

43 - 125 mm

Popular in	October	High demand for flights, 24% potential price rise
Cheapest in	July	Best time to find cheap flights, 26% potential price drop
Round-trip from	C$ 381	From Toronto Pearson Intl to Chicago Midway

Travellers have found it’s best to book a flight 60 days in advance to save up to 47% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Toronto Pearson Intl Airport to Chicago Midway Airport 1-2 weeks in advance for as low as C$ 396, or C$ 486 for flights within the next 24 hours.

Cheap flights from Pearson Intl to Midway in March, April 2023

15 Apr. - 2 May

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 30m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m

C$ 333

Delta

Pick Dates

Deal found 20/3

12 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 340

Delta

Pick Dates

Deal found 21/3

23 Apr. - 27 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 41m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 361

Delta

Pick Dates

Deal found 22/3

10 Apr. - 26 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 41m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 392

Delta

Pick Dates

Deal found 21/3

20 Apr. - 27 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 408

Delta

Pick Dates

Deal found 21/3

4 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 49m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 411

Delta

Pick Dates

Deal found 21/3

4 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 56m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 438

Delta

Pick Dates

Deal found 21/3

13 Apr. - 2 May

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m

C$ 460

Delta

Pick Dates

Deal found 20/3

20 Apr. - 27 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m

C$ 466

Delta

Pick Dates

Deal found 21/3

Pearson Intl to Midway 2023 flight deals

15 Apr. - 2 May

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 30m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m

C$ 333

Delta

Pick Dates

Deal found 20/3

12 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 340

Delta

Pick Dates

Deal found 21/3

23 Apr. - 27 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 41m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 361

Delta

Pick Dates

Deal found 22/3

10 Apr. - 25 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 392

Delta

Pick Dates

Deal found 21/3

20 Apr. - 27 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 408

Delta

Pick Dates

Deal found 21/3

4 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 49m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 411

Delta

Pick Dates

Deal found 21/3

19 Jun. - 20 Jun.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 06m

C$ 419

Delta

Pick Dates

Deal found 21/3

22 Jun. - 27 Jun.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 06m

C$ 424

Delta

Pick Dates

Deal found 21/3

4 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 56m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 438

Delta

Pick Dates

Deal found 21/3

Cheap Delta flights from Pearson Intl to Midway

15 Apr. - 2 May

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 30m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m

C$ 333

Delta

Pick Dates

Deal found 20/3

12 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 340

Delta

Pick Dates

Deal found 21/3

10 Apr. - 26 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 41m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 392

Delta

Pick Dates

Deal found 21/3

20 Apr. - 27 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 408

Delta

Pick Dates

Deal found 21/3

4 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 49m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 411

Delta

Pick Dates

Deal found 21/3

19 Jun. - 20 Jun.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 06m

C$ 419

Delta

Pick Dates

Deal found 21/3

22 Jun. - 27 Jun.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 31m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 06m

C$ 424

Delta

Pick Dates

Deal found 21/3

4 Apr. - 14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 56m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 438

Delta

Pick Dates

Deal found 21/3

13 Apr. - 2 May

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m

C$ 460

Delta

Pick Dates

Deal found 20/3

Cheap WestJet flights from Pearson Intl to Midway

21 Apr. - 22 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

17h 34m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

20h 35m

C$ 549

WestJet

Pick Dates

Deal found 21/3

22 Apr. - 29 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 21m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

4h 32m

C$ 557

WestJet

Pick Dates

Deal found 22/3

2 Aug. - 7 Aug.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 24m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 33m

C$ 582

WestJet

Pick Dates

Deal found 21/3

8 Apr. - 18 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 21m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

9h 27m

C$ 613

WestJet

Pick Dates

Deal found 21/3

21 Apr. - 24 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

24h 18m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

20h 07m

C$ 620

WestJet

Pick Dates

Deal found 21/3

27 Apr. - 30 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 07m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

4h 32m

C$ 624

WestJet

Pick Dates

Deal found 20/3

Last minute flights from Pearson Intl to Midway

1 Apr. - 8 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 21m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

3h 10m

C$ 568

Delta

Pick Dates

Deal found 21/3

27 Mar. - 31 Mar.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

21h 38m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 57m

C$ 659

Multiple Airlines

Pick Dates

Deal found 21/3

31 Mar. - 10 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 49m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 671

Delta

Pick Dates

Deal found 22/3

29 Mar. - 2 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 50m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

3h 52m

C$ 679

Delta

Pick Dates

Deal found 21/3

31 Mar. - 8 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 49m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

3h 10m

C$ 683

Delta

Pick Dates

Deal found 21/3

27 Mar. - 31 Mar.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 56m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 10m

C$ 691

Delta

Pick Dates

Deal found 22/3

31 Mar. - 11 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 57m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 08m

C$ 759

Delta

Pick Dates

Deal found 21/3

30 Mar. - 2 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 49m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

3h 52m

C$ 785

Endeavor Airlines

Pick Dates

Deal found 21/3

31 Mar. - 8 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 57m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

3h 10m

C$ 830

Delta

Pick Dates

Deal found 21/3

One-way flights to Midway from Pearson Intl

15 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 21m

C$ 192

Delta

Pick Dates

Deal found 21/3

14 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 31m

C$ 212

Delta

Pick Dates

Deal found 21/3

7 Jun.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

4h 16m

C$ 223

Delta

Pick Dates

Deal found 20/3

28 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

18h 43m

C$ 233

Multiple Airlines

Pick Dates

Deal found 21/3

20 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 00m

C$ 240

Delta

Pick Dates

Deal found 21/3

21 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

18h 43m

C$ 241

Multiple Airlines

Pick Dates

Deal found 21/3

5 Apr.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 57m

C$ 270

Delta

Pick Dates

Deal found 20/3

4 Jul.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 29m

C$ 278

Delta

Pick Dates

Deal found 21/3

11 May

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 37m

C$ 297

Delta

Pick Dates

Deal found 21/3

Find flights from Pearson Intl to Midway within your budget

Fly from

Fly to

Budget

C$ 333 - C$ 608

Route

Depart

Return

Price

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-15

1 stop5h 30m

Chicago Midway

2023-05-02

1 stop7h 50m

C$ 333

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-12

1 stop3h 31m

Chicago Midway

2023-04-14

1 stop8h 08m

C$ 340

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-10

1 stop7h 41m

Chicago Midway

2023-04-26

1 stop8h 08m

C$ 392

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-20

1 stop6h 00m

Chicago Midway

2023-04-27

1 stop8h 08m

C$ 408

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-04

1 stop3h 49m

Chicago Midway

2023-04-14

1 stop8h 08m

C$ 411

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-06-19

1 stop7h 31m

Chicago Midway

2023-06-20

1 stop8h 06m

C$ 419

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-21

1 stop17h 34m

Chicago Midway

2023-04-22

1 stop20h 35m

C$ 549

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-22

1 stop6h 21m

Chicago Midway

2023-04-29

1 stop4h 32m

C$ 557

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

2023-04-21

1 stop18h 43m

Chicago Midway

2023-04-24

2 stops29h 32m

C$ 608

Pick Dates

Flights are sorted by cheapest first

Deals found on 20/3

Related info for your journey

Alternative routes for Pearson Intl to Midway

Toronto Island to Midwayfrom C$ 245 pp

Pearson Intl to O'Hare Intlfrom C$ 436 pp

Top 2 airlines flying from Pearson Intl to Midway

Airline	Cheapest	Average	Flexibility	On-time	COVID-19 safety
Porter Airlines	CheapestC$ 229	AverageC$ 308	FlexibilityNo cancel fee	On-time52%	COVID-19 safety	Search Porter Airlines flights
Endeavor Airlines	CheapestC$ 547	AverageC$ 672	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Endeavor Airlines flights

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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 192

How to find the cheapest flight from Pearson Intl (YYZ) to Midway (MDW)

All the information you need to plan the best YYZ to MDW flight in 2023: compare Pearson Intl to Midway flight prices with the expected peak season, weather and rainfall in Midway.

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

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

When is the cheapest time to fly from Toronto Pearson Intl Airport to Chicago Midway Airport (YYZ - MDW)?

Cheap flights from Pearson Intl to Midway in March, April 2023

The best prices found for YYZ to MDW flights for March, April

Pearson Intl to Midway 2023 flight deals

Cheap flights to Midway from Pearson Intl found for this year

Cheap Delta flights from Pearson Intl to Midway

Cheap WestJet flights from Pearson Intl to Midway

Last minute flights from Pearson Intl to Midway

Late deals on round-trip flights to Midway from Pearson Intl, departing today and this week

One-way flights to Midway from Pearson Intl

The cheapest one-way flights from Pearson Intl to Midway

Find flights from Pearson Intl to Midway within your budget

Use the slider to find flights from Pearson Intl to Midway that fit your budget.

Related info for your journey

Useful info, stats and facts about Pearson Intl to Midway flights.

Which airlines flying from Toronto Pearson Intl to Chicago Midway have flexible cancellations due to COVID-19?

Can I find flights from Toronto Pearson Intl Airport to Chicago Midway Airport for under C$ 400 on Cheapflights?

Are there last-minute flights available from Toronto Pearson Intl Airport to Chicago Midway Airport for under C$ 600?

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

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

What are the cheapest flights from Toronto Pearson Intl Airport to Chicago Midway Airport?

What does YYZ to MDW mean?

Other flights from Pearson Intl

Other flights to Midway

Flights to Midway from Pearson Intl

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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.

Top 2 airlines flying from Pearson Intl to Midway

The chart below displays the airlines Cheapflights users travelling from Pearson Intl to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

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