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Cheap flights from Ontario to Chicago from C$ 160

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 20/1. 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.
Multiple Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 248Multiple Airlines
Thu, 5 Feb - Sun, 8 Feb
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$ 251Porter Airlines
Tue, 17 Feb - Wed, 25 Feb
Multiple Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 252Multiple Airlines
Thu, 19 Feb - Tue, 24 Feb
Porter Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 255Porter Airlines
Thu, 22 Jan - Thu, 29 Jan
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$ 256Porter Airlines
Sun, 18 Jan - Sun, 25 Jan
KLM Logo
7:45 a.m. - 12:51 p.m.
YYZ
-
MDW
6h 06m1 stop
KLM Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
C$ 286KLM
Wed, 4 Feb - Wed, 11 Feb
Delta Logo
6:15 a.m. - 12:46 p.m.
YYZ
-
MDW
7h 31m1 stop
Delta Logo
1:26 p.m. - 10:40 p.m.
MDW
-
YYZ
8h 14m1 stop
C$ 292Delta
Wed, 18 Feb - Thu, 19 Feb
Delta Logo
6:00 a.m. - 12:51 p.m.
YYZ
-
MDW
7h 51m1 stop
Delta Logo
9:53 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 06m1 stop
C$ 293Delta
Wed, 4 Feb - Wed, 11 Feb
WestJet Logo
8:10 p.m. - 6:36 p.m.
YXU
-
MDW
23h 26m2 stops
WestJet Logo
9:53 a.m. - 6:35 a.m.
MDW
-
YXU
19h 42m2 stops
C$ 1,938WestJet
Tue, 3 Feb - Tue, 10 Feb
WestJet Logo
8:10 p.m. - 6:36 p.m.
YXU
-
MDW
23h 26m2 stops
WestJet Logo
9:50 a.m. - 6:35 a.m.
MDW
-
YXU
19h 45m2 stops
C$ 2,131WestJet
Thu, 5 Feb - Thu, 12 Feb

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
22 Jan
YYZ6:14 p.m.Toronto Pearson Intl
16h 39m
1 stop
MDW9:53 a.m.Chicago Midway
23 Jan
MDW1:26 p.m.Chicago Midway
4h 42m
1 stop
YYZ7:08 p.m.Toronto Pearson Intl
C$ 369
Find similar
WestJet
12 Mar
YYZ10:05 a.m.Toronto Pearson Intl
3h 24m
1 stop
MDW12:29 p.m.Chicago Midway
15 Mar
MDW9:35 a.m.Chicago Midway
6h 42m
1 stop
YYZ5:17 p.m.Toronto Pearson Intl
C$ 374
Find similar
WestJet
13 Jan
YYZ7:45 a.m.Toronto Pearson Intl
6h 03m
1 stop
MDW12:48 p.m.Chicago Midway
16 Jan
MDW1:28 p.m.Chicago Midway
4h 45m
1 stop
YYZ7:13 p.m.Toronto Pearson Intl
C$ 376
Find similar

Porter Airlines flights from Region of Ontario to Chicago Midway Airport

Our best Porter Airlines deals on Region of Ontario to Chicago Midway Airport flight tickets
Porter Airlines
17 Feb
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
25 Feb
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 251
Find similar
Porter Airlines
12 Feb
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
15 Feb
MDW4:15 p.m.Chicago Midway
5h 30m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 253
Find similar
Porter Airlines
22 Jan
YTZ9:20 a.m.Toronto Island
1h 50m
MDW10:10 a.m.Chicago Midway
29 Jan
MDW11:05 a.m.Chicago Midway
1h 42m
YTZ1:47 p.m.Toronto Island
C$ 255
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 23 December 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 5/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/2

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

Nonstop1h 42m

C$ 248

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 17/2

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

Nonstop1h 50m

Chicago Midway

Wed 25/2

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

Nonstop1h 42m

C$ 251

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

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

Nonstop1h 50m

Chicago Midway

Tue 24/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 22/1

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Thu 29/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 18/1

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

Nonstop1h 50m

Chicago Midway

Sun 25/1

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

Nonstop1h 42m

C$ 256

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/2

7:45 a.m.-12:51 p.m.

1 stop6h 06m

Chicago Midway

Wed 11/2

9:33 a.m.-4:12 p.m.

1 stop5h 39m

C$ 286

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 18/2

6:15 a.m.-12:46 p.m.

1 stop7h 31m

Chicago Midway

Thu 19/2

1:26 p.m.-10:40 p.m.

1 stop8h 14m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/2

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 11/2

9:53 a.m.-3:59 p.m.

1 stop5h 06m

C$ 293

LondonChicago

YXU - MDW

YXUMDW

London

Tue 3/2

8:10 p.m.-6:36 p.m.

2 stops23h 26m

Chicago Midway

Tue 10/2

9:53 a.m.-6:35 a.m.

2 stops19h 42m

C$ 1,938

LondonChicago

YXU - MDW

YXUMDW

London

Thu 5/2

8:10 p.m.-6:36 p.m.

2 stops23h 26m

Chicago Midway

Thu 12/2

9:50 a.m.-6:35 a.m.

2 stops19h 45m

C$ 2,131

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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$ 237. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Region of Ontario during the month October is also very affordable. Most momondo users find prices during this month for around C$ 277.

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 Monday when prices can be found for as low as C$ 271. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday 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$ 305.

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$ 291. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 667.

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$ 176

Fastest flight time

1h 49m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Region of Ontario in the past 72 hours is C$ 176. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is C$ 253.
The fastest flight from Region of Ontario to Chicago Midway Airport takes 1h 49m
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$ 195Free CancellationRating
8.0
399 reviews
Search Porter Airlines 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.

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