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Cheap flights from Ontario to Chicago from C$ 237

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
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 389Porter Airlines
Thu, 22 Oct - Fri, 23 Oct
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
11:45 a.m. - 2:25 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 408Porter Airlines
Wed, 21 Oct - Sat, 24 Oct
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 409Porter Airlines
Mon, 19 Oct - Wed, 21 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 412Porter Airlines
Wed, 21 Oct - Thu, 22 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
11:45 a.m. - 2:25 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 416Porter Airlines
Tue, 13 Oct - Tue, 20 Oct
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 426Porter Airlines
Fri, 23 Oct - Fri, 23 Oct
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 437Porter Airlines
Mon, 19 Oct - Thu, 22 Oct
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 439Porter Airlines
Wed, 21 Oct - Thu, 22 Oct
Delta Logo
6:00 a.m. - 9:37 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
C$ 474Delta
Wed, 2 Dec - Sat, 5 Dec
Delta Logo
6:00 a.m. - 9:37 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
C$ 474Delta
Tue, 1 Dec - Sat, 5 Dec

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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
26 Nov
YYZ6:07 a.m.Toronto Pearson Intl
6h 25m
1 stop
MDW11:32 a.m.Chicago Midway
1 Dec
MDW6:48 p.m.Chicago Midway
3h 26m
1 stop
YYZ11:14 p.m.Toronto Pearson Intl
C$ 562
WestJet
31 Oct
YYZ6:07 a.m.Toronto Pearson Intl
7h 47m
1 stop
MDW12:54 p.m.Chicago Midway
3 Nov
MDW9:36 a.m.Chicago Midway
6h 50m
1 stop
YYZ5:26 p.m.Toronto Pearson Intl
C$ 567
WestJet
14 Oct
YYZ2:26 p.m.Toronto Pearson Intl
4h 34m
1 stop
MDW6:00 p.m.Chicago Midway
18 Oct
MDW6:44 p.m.Chicago Midway
3h 12m
1 stop
YYZ10:56 p.m.Toronto Pearson Intl
C$ 579

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
23 Nov
YYZ9:45 a.m.Toronto Pearson Intl
4h 06m
1 stop
MDW12:51 p.m.Chicago Midway
2 Dec
MDW9:37 a.m.Chicago Midway
6h 43m
1 stop
YYZ5:20 p.m.Toronto Pearson Intl
C$ 471
Delta
11 Nov
YYZ6:00 a.m.Toronto Pearson Intl
7h 51m
1 stop
MDW12:51 p.m.Chicago Midway
14 Nov
MDW6:44 p.m.Chicago Midway
3h 13m
1 stop
YYZ10:57 p.m.Toronto Pearson Intl
C$ 474
Delta
1 Dec
YYZ12:15 p.m.Toronto Pearson Intl
6h 46m
1 stop
MDW6:01 p.m.Chicago Midway
4 Dec
MDW6:41 p.m.Chicago Midway
3h 26m
1 stop
YYZ11:07 p.m.Toronto Pearson Intl
C$ 491

momondo Fare Finder

 
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 Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 22/10

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

Nonstop1h 50m

Chicago Midway

Fri 23/10

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

Nonstop1h 40m

C$ 389

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 21/10

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

Nonstop1h 50m

Chicago Midway

Sat 24/10

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

Nonstop1h 40m

C$ 408

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 19/10

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

Nonstop1h 50m

Chicago Midway

Wed 21/10

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

Nonstop1h 40m

C$ 409

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 21/10

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

Nonstop1h 50m

Chicago Midway

Thu 22/10

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

Nonstop1h 40m

C$ 412

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 13/10

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

Nonstop1h 50m

Chicago Midway

Tue 20/10

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

Nonstop1h 40m

C$ 416

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 23/10

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

Nonstop1h 50m

Chicago Midway

Fri 23/10

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

Nonstop1h 40m

C$ 426

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 19/10

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

Nonstop1h 50m

Chicago Midway

Thu 22/10

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

Nonstop1h 40m

C$ 437

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 21/10

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

Nonstop1h 50m

Chicago Midway

Thu 22/10

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

Nonstop1h 40m

C$ 439

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 2/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Sat 5/12

6:41 p.m.-11:07 p.m.

1 stop3h 26m

C$ 474

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 1/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Sat 5/12

6:41 p.m.-11:07 p.m.

1 stop3h 26m

C$ 474

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$ 290. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Region of Ontario during the month December is also very affordable. Most momondo users find prices during this month for around C$ 300.

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 Thursday when prices can be found for as low as C$ 332. 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$ 398.

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$ 342. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 688.

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$ 237

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$ 237. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is C$ 389.
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$ 254Free CancellationRating
8.0
467 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
Benton Harbor
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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