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Cheap flights from Ontario to Chicago from C$ 191

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 28/8. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 287Porter Airlines
Mon, 31 Aug - Wed, 2 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:45 a.m. - 2:25 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 289Porter Airlines
Thu, 27 Aug - Wed, 2 Sep
Air Transat Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 289Air Transat
Tue, 25 Aug - Thu, 27 Aug
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 289Porter Airlines
Fri, 28 Aug - Wed, 2 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 290Porter Airlines
Fri, 28 Aug - Wed, 2 Sep
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 290Porter Airlines
Mon, 7 Sep - Thu, 10 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 290Porter Airlines
Fri, 28 Aug - Tue, 1 Sep
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:45 a.m. - 2:25 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 292Porter Airlines
Sat, 29 Aug - Tue, 8 Sep
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$ 293Porter Airlines
Fri, 28 Aug - Thu, 3 Sep
Multiple Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 297Multiple Airlines
Thu, 20 Aug - Sun, 23 Aug

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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
2 Sep
YYZ12:09 p.m.Toronto Pearson Intl
5h 50m
1 stop
MDW4:59 p.m.Chicago Midway
8 Sep
MDW9:29 a.m.Chicago Midway
6h 51m
1 stop
YYZ5:20 p.m.Toronto Pearson Intl
C$ 329
Delta
7 Sep
YYZ6:10 a.m.Toronto Pearson Intl
7h 29m
1 stop
MDW12:39 p.m.Chicago Midway
15 Sep
MDW9:29 a.m.Chicago Midway
6h 51m
1 stop
YYZ5:20 p.m.Toronto Pearson Intl
C$ 341
Delta
7 Sep
YYZ6:10 a.m.Toronto Pearson Intl
7h 29m
1 stop
MDW12:39 p.m.Chicago Midway
10 Sep
MDW9:29 a.m.Chicago Midway
6h 51m
1 stop
YYZ5:20 p.m.Toronto Pearson Intl
C$ 359

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
31 Aug
YTZ8:55 a.m.Toronto Island
1h 50m
MDW9:45 a.m.Chicago Midway
2 Sep
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 287
Porter Airlines
28 Aug
YTZ8:55 a.m.Toronto Island
1h 50m
MDW9:45 a.m.Chicago Midway
2 Sep
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 290
Porter Airlines
29 Aug
YTZ8:50 a.m.Toronto Island
1h 50m
MDW9:40 a.m.Chicago Midway
8 Sep
MDW11:45 a.m.Chicago Midway
1h 40m
YTZ2:25 p.m.Toronto Island
C$ 292

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 1 August 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

Mon 31/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

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

Nonstop1h 40m

C$ 287

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 27/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

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

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

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

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 7/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Thu 10/9

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

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 1/9

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

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 29/8

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

Nonstop1h 50m

Chicago Midway

Tue 8/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 292

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

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

Nonstop1h 50m

Chicago Midway

Thu 3/9

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

Nonstop1h 40m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 23/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 297

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, January 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$ 286. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Region of Ontario during the month September is also very affordable. Most momondo users find prices during this month for around C$ 290.

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 Wednesday when prices can be found for as low as C$ 317. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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$ 361.

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 at noon. Flights from Region of Ontario to Chicago Midway Airport during this time can be as low as C$ 331. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 679.

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$ 181

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$ 181. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is C$ 287.
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$ 200Free CancellationRating
8.0
449 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
Valparaiso
Portage

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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