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Cheap flights from Ontario to Chicago from $129

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 11/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

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Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$184Porter Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$187Porter Airlines
Find Deal
Thu, Dec 4 - Fri, Dec 12
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$190Porter Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$191Porter Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
Delta Logo
7:45 am - 12:48 pmYYZ-MDW
6h 03m1 stop
Delta Logo
6:14 pm - 10:41 pmMDW-YYZ
3h 27m1 stop
$201Delta
Find Deal
Mon, Jan 5 - Mon, Jan 12
Delta Logo
6:30 am - 1:10 pmYYZ-MDW
7h 40m1 stop
Delta Logo
9:34 am - 2:48 pmMDW-YYZ
4h 14m1 stop
$210Delta
Find Deal
Tue, Dec 2 - Tue, Dec 9
KLM Logo
6:05 am - 12:34 pmYYZ-MDW
7h 29m1 stop
KLM Logo
9:34 am - 5:15 pmMDW-YYZ
6h 41m1 stop
$213KLM
Find Deal
Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Multiple Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$220Multiple Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$221Air Transat
Find Deal
Tue, Nov 18 - Fri, Nov 21
Multiple Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Multiple Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$227Multiple Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23

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
Jan 5
YYZ7:45 amToronto Pearson Intl
6h 03m
1 stop
MDW12:48 pmChicago Midway
Jan 12
MDW6:14 pmChicago Midway
3h 27m
1 stop
YYZ10:41 pmToronto Pearson Intl
$201
Find similar
Delta
Dec 2
YYZ6:30 amToronto Pearson Intl
7h 40m
1 stop
MDW1:10 pmChicago Midway
Dec 9
MDW9:34 amChicago Midway
4h 14m
1 stop
YYZ2:48 pmToronto Pearson Intl
$210
Find similar
Delta
Dec 11
YYZ6:05 amToronto Pearson Intl
3h 49m
1 stop
MDW8:54 amChicago Midway
Dec 14
MDW9:34 amChicago Midway
6h 41m
1 stop
YYZ5:15 pmToronto Pearson Intl
$222
Find similar

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
Dec 3
YYZ6:30 amToronto Pearson Intl
12h 48m
1 stop
MDW6:18 pmChicago Midway
Dec 10
MDW9:59 amChicago Midway
5h 16m
1 stop
YYZ4:15 pmToronto Pearson Intl
$275
Find similar
WestJet
Dec 2
YYZ6:30 pmToronto Pearson Intl
16h 24m
2 stops
MDW9:54 amChicago Midway
Dec 9
MDW10:49 amChicago Midway
12h 10m
1 stop
YYZ11:59 pmToronto Pearson Intl
$279
Find similar
WestJet
Dec 1
YYZ6:10 pmToronto Pearson Intl
16h 44m
1 stop
MDW9:54 amChicago Midway
Dec 8
MDW10:49 amChicago Midway
10h 09m
1 stop
YYZ9:58 pmToronto Pearson Intl
$280
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 832,500 searches. Data last updated November 4, 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

Thu 12/11

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 12/14

4:15 pm-6:57 pm

Nonstop1h 42m

$184

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/4

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Fri 12/12

4:15 pm-6:57 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/12

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 12/14

4:15 pm-6:57 pm

Nonstop1h 42m

$190

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/20

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 11/24

4:15 pm-6:57 pm

Nonstop1h 42m

$191

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 1/5

7:45 am-12:48 pm

1 stop6h 03m

Chicago Midway

Mon 1/12

6:14 pm-10:41 pm

1 stop3h 27m

$201

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 12/2

6:30 am-1:10 pm

1 stop7h 40m

Chicago Midway

Tue 12/9

9:34 am-2:48 pm

1 stop4h 14m

$210

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/11

6:05 am-12:34 pm

1 stop7h 29m

Chicago Midway

Sun 12/14

9:34 am-5:15 pm

1 stop6h 41m

$213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/21

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 11/23

4:15 pm-6:57 pm

Nonstop1h 42m

$220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 11/18

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 11/21

4:15 pm-6:57 pm

Nonstop1h 42m

$221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/20

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 11/23

4:15 pm-6:57 pm

Nonstop1h 42m

$227

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?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Region of Ontario, with most prices found around $172. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Region of Ontario during the month May is also very affordable. Most momondo users find prices during this month for around $206.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Region of Ontario. The lowest ticket price found for a Saturday departure recently was $228. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Region of Ontario because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $291.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Region of Ontario in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $242 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $333. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 4 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

$189

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 $189. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is $286.
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

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

    Prices for flights from Ontario to Chicago Midway Airport were last updated today.

  • 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?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago Midway Airport 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 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 $158Free CancellationRating
8.0
387 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Ontario to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

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

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

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