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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 292

YTZ — MDW
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Toronto Island to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Toronto Island to Midway

Tue 1/127:10 p.m. -
2 stops17h 23m
Thu 3/125:02 p.m. -
2 stops15h 37m
Deal found 26/10C$ 611
Tue 1/127:10 p.m. -
2 stops17h 23m
Sat 5/1212:28 p.m. -
2 stops20h 11m
Deal found 26/10C$ 641
Fri 20/117:10 p.m. -
2 stops13h 23m
Mon 23/111:16 p.m. -
2 stops22h 34m
Deal found 25/10C$ 652
Sat 21/114:30 p.m. -
2 stops16h 44m
Sun 22/111:16 p.m. -
2 stops19h 23m
Deal found 26/10C$ 671
Fri 20/117:10 p.m. -
2 stops19h 35m
Sun 22/111:16 p.m. -
2 stops21h 03m
Deal found 26/10C$ 678
Fri 11/127:10 p.m. -
2 stops17h 23m
Mon 14/125:02 p.m. -
2 stops17h 17m
Deal found 27/10C$ 681
Thu 19/117:35 a.m. -
2 stops11h 12m
Sun 22/111:16 p.m. -
2 stops19h 23m
Deal found 25/10C$ 687
Tue 1/127:10 p.m. -
2 stops17h 23m
Fri 4/125:02 p.m. -
2 stops19h 32m
Deal found 28/10C$ 692

Find flight deals from Toronto Island to Midway

Round-trip from

C$ 611

One-way from

C$ 292

Popular in

October

Cheapest in

January

Average price

C$ 766

Good round-trip deal

C$ 429 or less

Good one-way deal

C$ 186 or less
1/12-3/12
  • 1/12-3/12
  • 4 total stops
  • 33h 00m total
  • Toronto to Chicago
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1/12-31/12
  • 1/12-31/12
  • 2 total stops
  • 27h 23m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 28% potential increase in price (C$ 251 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 46 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Price to beat on a round-trip flight from Toronto Island to Chicago Midway.
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Price to beat on a one-way flight from Toronto Island to Chicago Midway.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Toronto Island Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 1/12

9:10 a.m.-11:33 a.m.

2 stops27h 23m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 292

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 25/11

9:10 a.m.-8:14 a.m.

2 stops24h 04m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 309

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 9/12

9:10 a.m.-4:06 p.m.

2 stops31h 56m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 329

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 4/1

9:05 a.m.-4:26 p.m.

2 stops32h 21m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 334

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 21/11

9:10 a.m.-8:14 a.m.

2 stops24h 04m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 338

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 22/11

9:10 a.m.-12:21 p.m.

2 stops28h 11m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 343

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 14/12

4:15 p.m.-11:33 a.m.

2 stops20h 18m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 350

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 9/11

7:00 a.m.-5:47 p.m.

3 stops35h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 372
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 4/12

7:10 p.m.-11:33 a.m.

2 stops17h 23m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 386

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 13/11

4:30 p.m.-5:47 p.m.

2 stops26h 17m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 403

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 19 resultsSorted by cheapest first
1
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Best time to book a flight from Toronto Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto Island with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Toronto Island Airport to Chicago Midway Airport

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Toronto Island Airport to Chicago Midway Airport as you normally would.

How much does it cost to fly round-trip from Toronto Island Airport to Chicago Midway Airport?

Airfare is above average for this route at the moment.

Toronto Island Airport to Chicago Midway Airport flights typically cost between C$ 336 and C$ 606 in December.
The cheapest round-trip price found within the last 5 days was C$ 611 on Multiple Airlines (1 Dec-3 Dec).

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines from Toronto Island Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
467 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?

    According to our current data, Porter Airlines (C$ 250), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 44% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Toronto Island Airport to Chicago Midway Airport?

    No one likes to see their flight delayed. When booking a flight from Toronto Island Airport to Chicago Midway Airport consider choosing Porter Airlines (74%), Porter Airlines (74%) or Air Transat (74%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Toronto Island Airport to Chicago Midway Airport?

    On average you can expect to pay C$ 399 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 170 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 687.

  • Can I find deals for flights from Toronto Island to Midway that include hotel bookings?

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

  • How can I find direct flights from Toronto Island to Midway?

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

  • Can I find deals for business class flights from Toronto Island to Midway?

    Yes. Cheapflights offers flight deals from Toronto Island 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Toronto Island to Midway

Pearson Intl to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Pearson Intl to Midway flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights

Top airline flying from Toronto Island to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 250AverageC$ 340FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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