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Cheap flights from Ontario to Chicago from C$ 174

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 2/6. 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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Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 275Porter Airlines
Wed, 24 Jun - Fri, 26 Jun
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:15 p.m. - 5:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 276Porter Airlines
Wed, 24 Jun - Fri, 24 Jul
Porter Airlines Logo
8:45 a.m. - 9:35 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:15 a.m. - 12:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 277Porter Airlines
Wed, 10 Jun - Fri, 12 Jun
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 279Porter Airlines
Thu, 11 Jun - Sun, 14 Jun
Delta Logo
2:29 p.m. - 6:31 p.m.
YYZ
-
MDW
5h 02m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 330Delta
Fri, 12 Jun - Sun, 14 Jun
Delta Logo
2:29 p.m. - 6:31 p.m.
YYZ
-
MDW
5h 02m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 331Delta
Thu, 11 Jun - Tue, 23 Jun
Multiple Airlines Logo
6:55 a.m. - 9:40 a.m.
YOW
-
MDW
27h 45m
1 stop
Multiple Airlines Logo
10:25 a.m. - 12:20 a.m.
MDW
-
YOW
12h 55m
1 stop
C$ 505Multiple Airlines
Wed, 17 Jun - Wed, 24 Jun
Multiple Airlines Logo
6:55 a.m. - 9:35 a.m.
YOW
-
MDW
27h 40m
1 stop
Multiple Airlines Logo
10:15 a.m. - 12:20 a.m.
MDW
-
YOW
13h 05m
1 stop
C$ 533Multiple Airlines
Wed, 3 Jun - Wed, 10 Jun
WestJet Logo
6:10 a.m. - 12:46 p.m.
YXU
-
MDW
31h 36m
3 stops
WestJet Logo
1:18 p.m. - 1:50 p.m.
MDW
-
YXU
23h 32m
3 stops
C$ 1,671WestJet
Sat, 4 Jul - Sat, 11 Jul
WestJet Logo
6:10 a.m. - 12:46 p.m.
YXU
-
MDW
31h 36m
3 stops
WestJet Logo
6:35 p.m. - 1:50 p.m.
MDW
-
YXU
18h 15m
3 stops
C$ 1,816WestJet
Sat, 4 Jul - Sat, 11 Jul

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
12 Jun
YYZ2:29 p.m.Toronto Pearson Intl
5h 02m
1 stop
MDW6:31 p.m.Chicago Midway
13 Jun
MDW6:35 p.m.Chicago Midway
3h 27m
1 stop
YYZ11:02 p.m.Toronto Pearson Intl
C$ 330
Delta
11 Jun
YYZ2:29 p.m.Toronto Pearson Intl
5h 02m
1 stop
MDW6:31 p.m.Chicago Midway
23 Jun
MDW1:26 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:02 p.m.Toronto Pearson Intl
C$ 331
Delta
9 Jun
YYZ6:05 a.m.Toronto Pearson Intl
4h 09m
1 stop
MDW9:14 a.m.Chicago Midway
10 Jun
MDW9:17 a.m.Chicago Midway
3h 17m
1 stop
YYZ1:34 p.m.Toronto Pearson Intl
C$ 348

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
24 Jun
YTZ8:50 a.m.Toronto Island
1h 50m
MDW9:40 a.m.Chicago Midway
26 Jun
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 275
Porter Airlines
24 Jun
YTZ8:50 a.m.Toronto Island
1h 50m
MDW9:40 a.m.Chicago Midway
24 Jul
MDW3:15 p.m.Chicago Midway
1h 40m
YTZ5:55 p.m.Toronto Island
C$ 276
Porter Airlines
10 Jun
YTZ8:45 a.m.Toronto Island
1h 50m
MDW9:35 a.m.Chicago Midway
12 Jun
MDW10:15 a.m.Chicago Midway
1h 40m
YTZ12:55 p.m.Toronto Island
C$ 277

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 22 May 2026.
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

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 24/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Fri 26/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 24/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Fri 24/7

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 276

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 10/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Fri 12/6

10:15 a.m.-12:55 p.m.

Nonstop1h 40m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 279

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 12/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

Chicago Midway

Sun 14/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 330

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

Chicago Midway

Tue 23/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 331

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 17/6

6:55 a.m.-9:40 a.m.

1 stop27h 45m

Chicago Midway

Wed 24/6

10:25 a.m.-12:20 a.m.

1 stop12h 55m

C$ 505

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 3/6

6:55 a.m.-9:35 a.m.

1 stop27h 40m

Chicago Midway

Wed 10/6

10:15 a.m.-12:20 a.m.

1 stop13h 05m

C$ 533

LondonChicago

YXU - MDW

YXUMDW

London

Sat 4/7

6:10 a.m.-12:46 p.m.

3 stops31h 36m

Chicago Midway

Sat 11/7

1:18 p.m.-1:50 p.m.

3 stops23h 32m

C$ 1,671

LondonChicago

YXU - MDW

YXUMDW

London

Sat 4/7

6:10 a.m.-12:46 p.m.

3 stops31h 36m

Chicago Midway

Sat 11/7

6:35 p.m.-1:50 p.m.

3 stops18h 15m

C$ 1,816

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, June 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$ 110. If you are unable to visit Chicago Midway Airport during the month of June, then departing from Region of Ontario during the month August is also very affordable. Most momondo users find prices during this month for around C$ 113.

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$ 287. 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$ 318.

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$ 292. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 669.

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 Region of Ontario to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Region of Ontario to Chicago Midway Airport 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$ 155

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$ 155. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is C$ 290.
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

Frequently asked questions about flying from Ontario to Chicago Midway Airport

  • 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$ 113Free CancellationRating
8.0
439 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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

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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