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Cheap flights from Chicago to Ontario from C$ 109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Ontario departing on 1/2. 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 Chicago to Ontario

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 261Porter Airlines
Tue, 27 Jan - Tue, 3 Feb
Porter Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 264Porter Airlines
Thu, 5 Feb - Tue, 10 Feb
United Airlines Logo
11:15 a.m. - 2:01 p.m.
ORD
-
YYZ
1h 46mdirect
United Airlines Logo
9:00 p.m. - 10:05 p.m.
YYZ
-
ORD
2h 05mdirect
C$ 281United Airlines
Thu, 5 Feb - Sun, 8 Feb
Air Canada Logo
8:40 p.m. - 11:19 p.m.
ORD
-
YYZ
1h 39mdirect
Air Canada Logo
6:15 a.m. - 11:06 a.m.
YYZ
-
ORD
5h 51m1 stop
C$ 283Air Canada
Tue, 3 Feb - Thu, 5 Feb
Multiple Airlines Logo
5:15 a.m. - 11:20 p.m.
ORD
-
YYZ
17h 05m1 stop
Multiple Airlines Logo
8:15 a.m. - 9:13 a.m.
YYZ
-
ORD
1h 58mdirect
C$ 285Multiple Airlines
Wed, 4 Feb - Wed, 11 Feb
Air Canada Logo
8:00 a.m. - 10:40 a.m.
ORD
-
YYZ
1h 40mdirect
Air Canada Logo
6:15 a.m. - 11:06 a.m.
YYZ
-
ORD
5h 51m1 stop
C$ 286Air Canada
Wed, 11 Feb - Sat, 14 Feb
Multiple Airlines Logo
5:32 p.m. - 11:20 p.m.
ORD
-
YYZ
28h 48m1 stop
Multiple Airlines Logo
7:35 a.m. - 10:08 p.m.
YYZ
-
ORD
15h 33m1 stop
C$ 288Multiple Airlines
Tue, 3 Feb - Tue, 10 Feb
United Airlines Logo
6:00 p.m. - 9:17 p.m.
ORD
-
YUL
2h 17mdirect
United Airlines Logo
6:00 a.m. - 8:00 a.m.
YUL
-
ORD
3h 00mdirect
C$ 293United Airlines
Sat, 14 Feb - Sun, 15 Feb
American Airlines Logo
10:10 a.m. - 5:40 p.m.
ORD
-
YYZ
6h 30m1 stop
American Airlines Logo
4:44 p.m. - 5:44 p.m.
YYZ
-
ORD
2h 00mdirect
C$ 294American Airlines
Tue, 3 Feb - Sat, 7 Feb
American Airlines Logo
8:12 a.m. - 10:44 p.m.
ORD
-
YUL
13h 32m1 stop
American Airlines Logo
7:30 a.m. - 6:34 p.m.
YUL
-
ORD
12h 04m1 stop
C$ 296American Airlines
Wed, 4 Feb - Mon, 9 Feb

Air Canada flights from Chicago to Region of Ontario

Our best Air Canada deals on Chicago to Region of Ontario flight tickets
Air Canada
3 Feb
ORD8:40 p.m.Chicago O'Hare Intl
1h 39m
YYZ11:19 p.m.Toronto Pearson Intl
5 Feb
YYZ6:15 a.m.Toronto Pearson Intl
5h 51m
1 stop
ORD11:06 a.m.Chicago O'Hare Intl
C$ 283
Air Canada
11 Feb
ORD8:00 a.m.Chicago O'Hare Intl
1h 40m
YYZ10:40 a.m.Toronto Pearson Intl
14 Feb
YYZ6:15 a.m.Toronto Pearson Intl
5h 51m
1 stop
ORD11:06 a.m.Chicago O'Hare Intl
C$ 286
Air Canada
3 Feb
ORD7:15 a.m.Chicago O'Hare Intl
2h 05m
YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl
10 Feb
YUL6:25 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 p.m.Chicago O'Hare Intl
C$ 292

American Airlines flights from Chicago to Region of Ontario

Our best American Airlines deals on Chicago to Region of Ontario flight tickets
American Airlines
3 Feb
ORD10:10 a.m.Chicago O'Hare Intl
6h 30m
1 stop
YYZ5:40 p.m.Toronto Pearson Intl
7 Feb
YYZ4:44 p.m.Toronto Pearson Intl
2h 00m
ORD5:44 p.m.Chicago O'Hare Intl
C$ 294
American Airlines
4 Feb
ORD8:12 a.m.Chicago O'Hare Intl
13h 32m
1 stop
YUL10:44 p.m.Montreal Pierre Elliott Trudeau Intl
9 Feb
YUL7:30 a.m.Montreal Pierre Elliott Trudeau Intl
12h 04m
1 stop
ORD6:34 p.m.Chicago O'Hare Intl
C$ 296
American Airlines
5 Feb
ORD9:41 a.m.Chicago O'Hare Intl
1h 53m
YYZ12:34 p.m.Toronto Pearson Intl
8 Feb
YYZ4:30 p.m.Toronto Pearson Intl
7h 57m
1 stop
ORD11:27 p.m.Chicago O'Hare Intl
C$ 301

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Region of Ontario 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 8 January 2026.
Use the filters below to find and compare flights from Chicago to Ontario that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 27/1

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

Nonstop1h 42m

Toronto Island

Tue 3/2

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

Nonstop1h 50m

C$ 261

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/2

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

Nonstop1h 42m

Toronto Island

Tue 10/2

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

Nonstop1h 50m

C$ 264

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 5/2

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

Toronto Pearson Intl

Sun 8/2

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

C$ 281

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 3/2

8:40 p.m.-11:19 p.m.

Nonstop1h 39m

Toronto Pearson Intl

Thu 5/2

6:15 a.m.-11:06 a.m.

1 stop5h 51m

C$ 283

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-11:20 p.m.

1 stop17h 05m

Toronto Pearson Intl

Wed 11/2

8:15 a.m.-9:13 a.m.

Nonstop1h 58m

C$ 285

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 11/2

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

Toronto Pearson Intl

Sat 14/2

6:15 a.m.-11:06 a.m.

1 stop5h 51m

C$ 286

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 3/2

5:32 p.m.-11:20 p.m.

1 stop28h 48m

Toronto Pearson Intl

Tue 10/2

7:35 a.m.-10:08 p.m.

1 stop15h 33m

C$ 288

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sat 14/2

6:00 p.m.-9:17 p.m.

Nonstop2h 17m

Montreal Pierre Elliott Trudeau Intl

Sun 15/2

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

Nonstop3h 00m

C$ 293

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 3/2

10:10 a.m.-5:40 p.m.

1 stop6h 30m

Toronto Pearson Intl

Sat 7/2

4:44 p.m.-5:44 p.m.

Nonstop2h 00m

C$ 294

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Wed 4/2

8:12 a.m.-10:44 p.m.

1 stop13h 32m

Montreal Pierre Elliott Trudeau Intl

Mon 9/2

7:30 a.m.-6:34 p.m.

1 stop12h 04m

C$ 296

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 Ontario from

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

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 Region of Ontario?

In general, September is the cheapest month to fly from Chicago to Region of Ontario. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 289. If you are unable to visit Region of Ontario during the month of September, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around C$ 323.

What is the cheapest day to depart on your flight to Region of Ontario?

The cheapest day to depart from Chicago to Region of Ontario is on a Thursday. Travellers who choose to depart for Region of Ontario on a Thursday will often find tickets for as low as C$ 332. The most expensive day to fly to Region of Ontario is Monday, with ticket prices averaging around C$ 485.

What is the cheapest time of day to depart on your flight to Region of Ontario?

Our most recent data shows that the best time of day to fly to Region of Ontario is in the evening. Flights from Chicago to Region of Ontario during this time can be as low as C$ 288. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 468 on average. Flights to Region of Ontario from Chicago in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Chicago to Ontario flight route?

Fly from Chicago O'Hare Intl to Toronto Pearson Intl for the best Chicago - Ontario flight prices

How far in advance should I book a flight to Region of Ontario?

You are more likely to see cheaper flights to Region of Ontario from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Region of Ontario for around C$ 401 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Region of Ontario from Chicago for as low as C$ 210 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Ontario 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 Chicago to Region of Ontario flights?

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

Cheap Chicago to Region of Ontario flight deals and tips

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

Best price found

C$ 181

Fastest flight time

1h 39m

Direct flights

Every day

Airports in Region of Ontario

123 airports
The best one-way flight to Region of Ontario from Chicago in the past 72 hours is C$ 181. The best round-trip flight deal from Chicago to Region of Ontario found on momondo in the last 72 hours is C$ 270.
The fastest flight from Chicago to Region of Ontario takes 1h 39m
Direct flights go from Chicago to Region of Ontario every day.
There are 123 airports in Region of Ontario. From Chicago there are direct flights to Toronto Pearson Intl (YYZ), Toronto Island (YTZ).
Search flight deals

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

    Prices for flights from Chicago to Ontario refresh daily.

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

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

    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 Chicago to Ontario.

  • What documentation or ID do you need to fly to Ontario?

    The necessary travel and health documents for your Ontario trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Chicago to Region of Ontario

Compare and see reviews for airlines that fly from Chicago to Region of Ontario with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom C$ 151Free CancellationRating
7.2
11,095 reviews
Search American Airlines flights
Air CanadaPriceFrom C$ 203Free CancellationRating
7.1
10,603 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 260Free CancellationRating
7.4
9,141 reviews
Search United Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Ontario for you.

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

Yes. momondo allows you to filter the results for Chicago to Ontario flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Ontario from Chicago.

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

Yes. momondo can track prices for Chicago to Ontario flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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