Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Ontario to Chicago from C$ 134

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 5/9. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 206Porter Airlines
Find Deal
Tue, 16 Sep - Mon, 22 Sep
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 208Porter Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
Air Transat Logo
9:00 a.m. - 9:50 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 230Air Transat
Find Deal
Mon, 1 Sep - Wed, 3 Sep
Air Transat Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 259Air Transat
Find Deal
Tue, 7 Oct - Wed, 22 Oct
Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 271
Find Deal
Thu, 25 Sep - Mon, 29 Sep
Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 277
Find Deal
Wed, 27 Aug - Wed, 3 Sep
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
Delta Logo
6:15 p.m. - 10:56 p.m.MDW-YYZ
3h 41m1 stop
C$ 293Delta
Find Deal
Sat, 13 Sep - Sat, 20 Sep
Delta Logo
6:00 a.m. - 8:35 a.m.YUL-MDW
3h 35m1 stop
Delta Logo
6:00 a.m. - 1:38 p.m.MDW-YUL
6h 38m1 stop
C$ 298Delta
Find Deal
Wed, 3 Sep - Sat, 6 Sep
WestJet Logo
1:20 p.m. - 10:14 p.m.YYZ-MDW
9h 54m1 stop
WestJet Logo
9:20 a.m. - 6:12 a.m.MDW-YYZ
19h 52m2 stops
C$ 389WestJet
Find Deal
Fri, 17 Oct - Tue, 21 Oct
WestJet Logo
1:20 p.m. - 9:44 p.m.YYZ-MDW
9h 24m1 stop
WestJet Logo
10:31 a.m. - 4:57 p.m.MDW-YYZ
5h 26m1 stop
C$ 400WestJet
Find Deal
Thu, 21 Aug - Mon, 25 Aug

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
16 Sep
YTZ3:35 p.m.Toronto Island
1h 49m
MDW4:24 p.m.Chicago Midway
22 Sep
MDW5:20 p.m.Chicago Midway
1h 42m
YTZ8:02 p.m.Toronto Island
C$ 206
Find similar
Porter Airlines
4 Sep
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
7 Sep
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 208
Find similar
Porter Airlines
4 Sep
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
7 Sep
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 209
Find similar

Air Transat flights from Region of Ontario to Chicago Midway Airport

Our best Air Transat deals on Region of Ontario to Chicago Midway Airport flight tickets
Air Transat
1 Sep
YTZ9:00 a.m.Toronto Island
1h 50m
MDW9:50 a.m.Chicago Midway
3 Sep
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 230
Find similar
Air Transat
7 Oct
YTZ3:35 p.m.Toronto Island
1h 49m
MDW4:24 p.m.Chicago Midway
22 Oct
MDW5:20 p.m.Chicago Midway
1h 42m
YTZ8:02 p.m.Toronto Island
C$ 259
Find similar
Air Transat
24 Aug
YTZ7:55 a.m.Toronto Island
1h 50m
MDW8:45 a.m.Chicago Midway
31 Aug
MDW10:40 a.m.Chicago Midway
1h 40m
YTZ1:20 p.m.Toronto Island
C$ 284
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 31 July 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

Tue 16/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 22/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 206

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 7/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 1/9

9:00 a.m.-9:50 a.m.

Nonstop1h 50m

Chicago Midway

Wed 3/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 230

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 7/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Wed 22/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 29/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 271

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 27/8

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Wed 3/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 13/9

12:14 p.m.-6:35 p.m.

1 stop7h 21m

Chicago Midway

Sat 20/9

6:15 p.m.-10:56 p.m.

1 stop3h 41m

C$ 293

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/9

6:00 a.m.-8:35 a.m.

1 stop3h 35m

Chicago Midway

Sat 6/9

6:00 a.m.-1:38 p.m.

1 stop6h 38m

C$ 298

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 17/10

1:20 p.m.-10:14 p.m.

1 stop9h 54m

Chicago Midway

Tue 21/10

9:20 a.m.-6:12 a.m.

2 stops19h 52m

C$ 389

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 21/8

1:20 p.m.-9:44 p.m.

1 stop9h 24m

Chicago Midway

Mon 25/8

10:31 a.m.-4:57 p.m.

1 stop5h 26m

C$ 400

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, May 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$ 285. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Region of Ontario during the month February is also very affordable. Most momondo users find prices during this month for around C$ 295.

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 Tuesday when prices can be found for as low as C$ 324. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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$ 346.

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$ 325. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 574.

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 are 1 cabin classes 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$ 134

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$ 134. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is C$ 206.
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$ 228Free CancellationRating
8.0
318 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 477Free CancellationRating
7.2
2,978 reviews
Search WestJet flights

Travelling to a place near Chicago?

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 5/8
Tue 12/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago