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Cheap flights from Ontario to Chicago from C$ 181

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ontario to Chicago departing on 23/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 258Porter Airlines
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 263Porter Airlines
Find Deal
Thu, 4 Dec - Fri, 12 Dec
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 267Porter Airlines
Find Deal
Fri, 12 Dec - Sun, 14 Dec
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 268Porter Airlines
Find Deal
Thu, 20 Nov - Sun, 23 Nov
Delta Logo
7:45 a.m. - 12:48 p.m.YYZ-MDW
6h 03m1 stop
Delta Logo
1:28 p.m. - 7:13 p.m.MDW-YYZ
4h 45m1 stop
C$ 282Delta
Find Deal
Mon, 5 Jan - Sun, 11 Jan
Delta Logo
6:05 a.m. - 8:54 a.m.YYZ-MDW
3h 49m1 stop
Delta Logo
1:14 p.m. - 5:15 p.m.MDW-YYZ
3h 01m1 stop
C$ 295Delta
Find Deal
Tue, 2 Dec - Tue, 9 Dec
KLM Logo
6:05 a.m. - 12:34 p.m.YYZ-MDW
7h 29m1 stop
KLM Logo
9:34 a.m. - 5:15 p.m.MDW-YYZ
6h 41m1 stop
C$ 299KLM
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 309Multiple Airlines
Find Deal
Fri, 21 Nov - Mon, 24 Nov
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 310Air Transat
Find Deal
Tue, 18 Nov - Fri, 21 Nov
Multiple Airlines Logo
7:10 a.m. - 8:45 p.m.YYZ-MDW
14h 35m1 stop
Multiple Airlines Logo
9:43 p.m. - 2:20 p.m.MDW-YYZ
15h 37m1 stop
C$ 366Multiple Airlines
Find Deal
Fri, 16 Jan - Sun, 18 Jan

Delta flights from Region of Ontario to Chicago Midway Airport

Our best Delta deals on Region of Ontario to Chicago Midway Airport flight tickets
Delta
5 Jan
YYZ7:45 a.m.Toronto Pearson Intl
6h 03m
1 stop
MDW12:48 p.m.Chicago Midway
11 Jan
MDW1:28 p.m.Chicago Midway
4h 45m
1 stop
YYZ7:13 p.m.Toronto Pearson Intl
C$ 282
Find similar
Delta
2 Dec
YYZ6:05 a.m.Toronto Pearson Intl
3h 49m
1 stop
MDW8:54 a.m.Chicago Midway
9 Dec
MDW1:14 p.m.Chicago Midway
3h 01m
1 stop
YYZ5:15 p.m.Toronto Pearson Intl
C$ 295
Find similar
Delta
11 Dec
YYZ12:13 p.m.Toronto Pearson Intl
6h 47m
1 stop
MDW6:00 p.m.Chicago Midway
15 Dec
MDW9:34 a.m.Chicago Midway
4h 14m
1 stop
YYZ2:48 p.m.Toronto Pearson Intl
C$ 312
Find similar

WestJet flights from Region of Ontario to Chicago Midway Airport

Our best WestJet deals on Region of Ontario to Chicago Midway Airport flight tickets
WestJet
3 Dec
YYZ6:30 a.m.Toronto Pearson Intl
12h 48m
1 stop
MDW6:18 p.m.Chicago Midway
10 Dec
MDW9:59 a.m.Chicago Midway
5h 16m
1 stop
YYZ4:15 p.m.Toronto Pearson Intl
C$ 386
Find similar
WestJet
2 Dec
YYZ6:30 p.m.Toronto Pearson Intl
16h 24m
2 stops
MDW9:54 a.m.Chicago Midway
9 Dec
MDW10:49 a.m.Chicago Midway
12h 10m
1 stop
YYZ11:59 p.m.Toronto Pearson Intl
C$ 392
Find similar
WestJet
1 Dec
YYZ6:10 p.m.Toronto Pearson Intl
16h 44m
1 stop
MDW9:54 a.m.Chicago Midway
8 Dec
MDW10:49 a.m.Chicago Midway
10h 09m
1 stop
YYZ9:58 p.m.Toronto Pearson Intl
C$ 393
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Region of Ontario to Chicago Midway Airport 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, momondo users made 96,600 searches. Data last updated 4 November 2025.
Use the filters below to find and compare flights from Ontario to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Fri 12/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 267

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 23/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 268

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Sun 11/1

1:28 p.m.-7:13 p.m.

1 stop4h 45m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 2/12

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Tue 9/12

1:14 p.m.-5:15 p.m.

1 stop3h 01m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/12

6:05 a.m.-12:34 p.m.

1 stop7h 29m

Chicago Midway

Sun 14/12

9:34 a.m.-5:15 p.m.

1 stop6h 41m

C$ 299

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 21/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 24/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 309

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 18/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Fri 21/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 310

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 16/1

7:10 a.m.-8:45 p.m.

1 stop14h 35m

Chicago Midway

Sun 18/1

9:43 p.m.-2:20 p.m.

1 stop15h 37m

C$ 366

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Region of Ontario to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

In general, September is the cheapest month to fly from Region of Ontario to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 241. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Region of Ontario during the month May is also very affordable. Most momondo users find prices during this month for around C$ 289.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Friday when prices can be found for as low as C$ 304. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Region of Ontario because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 330.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Region of Ontario to Chicago Midway Airport during this time can be as low as C$ 311. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 680.

What is the cheapest Ontario to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago Midway flight prices

What cabin class options are available on Ontario to Chicago Midway flights?

There is only 1 cabin class available to choose from on Ontario to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago Midway Airport.

Cheap Region of Ontario to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago Midway Airport

Best price found

C$ 198

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Region of Ontario in the past 72 hours is C$ 198. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is C$ 347.
The fastest flight from Region of Ontario to Chicago Midway Airport takes 1h 50m
Direct flights go from Region of Ontario to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Ontario to Chicago Midway Airport?

    Prices for flights from Ontario to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Ontario to Chicago Midway Airport?

  • How old do you have to be to fly from Ontario to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Ontario to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Region of Ontario to Chicago Midway Airport?

Best airlines flying from Region of Ontario to Chicago Midway Airport

Compare and see reviews for airlines that fly from Region of Ontario to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 199Free CancellationRating
8.0
387 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 557Free CancellationRating
7.2
3,153 reviews
Search WestJet flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Ontario to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Ontario which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Ontario to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Ontario. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Ontario to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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