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Cheap flights from Ontario to Chicago from $136

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 7/24. 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
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$205Porter Airlines
Fri, Jul 17 - Mon, Jul 20
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
$207Porter Airlines
Wed, Jul 29 - Wed, Aug 5
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:15 pm - 5:55 pm
MDW
-
YTZ
1h 40mnonstop
$208Porter Airlines
Mon, Aug 17 - Mon, Aug 24
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
$209Porter Airlines
Mon, Aug 3 - Fri, Aug 7
Delta Logo
12:10 pm - 6:05 pm
YYZ
-
MDW
6h 55m
1 stop
Delta Logo
1:00 pm - 5:22 pm
MDW
-
YYZ
3h 22m
1 stop
$248Delta
Thu, Oct 29 - Mon, Nov 23
Delta Logo
6:00 am - 9:07 am
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
9:29 am - 5:20 pm
MDW
-
YYZ
6h 51m
1 stop
$255Delta
Thu, Oct 1 - Fri, Oct 2
Multiple Airlines Logo
6:25 pm - 9:45 am
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:15 pm - 8:04 pm
MDW
-
YOW
3h 49m
1 stop
$385Multiple Airlines
Thu, Aug 6 - Sun, Aug 9
Multiple Airlines Logo
6:55 am - 2:35 pm
YOW
-
MDW
8h 40m
1 stop
Multiple Airlines Logo
10:20 am - 5:54 pm
MDW
-
YOW
6h 34m
1 stop
$398Multiple Airlines
Thu, Jul 30 - Sun, Aug 2
WestJet Logo
8:40 pm - 9:59 am
YXU
-
MDW
14h 19m
2 stops
WestJet Logo
1:25 pm - 5:20 am
MDW
-
YXU
14h 55m
2 stops
$1,061WestJet
Tue, Aug 4 - Tue, Aug 11
WestJet Logo
8:40 pm - 6:01 pm
YXU
-
MDW
22h 21m
2 stops
WestJet Logo
9:59 am - 5:20 am
MDW
-
YXU
18h 21m
2 stops
$1,308WestJet
Fri, Aug 21 - Tue, Aug 25

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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
Jul 17
YTZ1:45 pmToronto Island
1h 50m
MDW2:35 pmChicago Midway
Jul 19
MDW3:20 pmChicago Midway
1h 40m
YTZ6:00 pmToronto Island
$205
Porter Airlines
Jul 29
YTZ1:45 pmToronto Island
1h 50m
MDW2:35 pmChicago Midway
Aug 5
MDW10:25 amChicago Midway
1h 40m
YTZ1:05 pmToronto Island
$207
Porter Airlines
Aug 17
YTZ1:45 pmToronto Island
1h 50m
MDW2:35 pmChicago Midway
Aug 24
MDW3:15 pmChicago Midway
1h 40m
YTZ5:55 pmToronto Island
$208

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
Oct 29
YYZ12:10 pmToronto Pearson Intl
6h 55m
1 stop
MDW6:05 pmChicago Midway
Nov 23
MDW1:00 pmChicago Midway
3h 22m
1 stop
YYZ5:22 pmToronto Pearson Intl
$248
Delta
Oct 1
YYZ6:00 amToronto Pearson Intl
4h 07m
1 stop
MDW9:07 amChicago Midway
Oct 2
MDW9:29 amChicago Midway
6h 51m
1 stop
YYZ5:20 pmToronto Pearson Intl
$255
Delta
Sep 5
YYZ12:09 pmToronto Pearson Intl
5h 50m
1 stop
MDW4:59 pmChicago Midway
Sep 8
MDW5:45 pmChicago Midway
4h 14m
1 stop
YYZ10:59 pmToronto Pearson Intl
$256

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 July 5, 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

Fri 7/17

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Mon 7/20

3:20 pm-6:00 pm

Nonstop1h 40m

$205

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/29

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Wed 8/5

10:25 am-1:05 pm

Nonstop1h 40m

$207

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/17

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Mon 8/24

3:15 pm-5:55 pm

Nonstop1h 40m

$208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/3

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Fri 8/7

10:25 am-1:05 pm

Nonstop1h 40m

$209

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/29

12:10 pm-6:05 pm

1 stop6h 55m

Chicago Midway

Mon 11/23

1:00 pm-5:22 pm

1 stop3h 22m

$248

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/1

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Fri 10/2

9:29 am-5:20 pm

1 stop6h 51m

$255

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 8/6

6:25 pm-9:45 am

1 stop16h 20m

Chicago Midway

Sun 8/9

3:15 pm-8:04 pm

1 stop3h 49m

$385

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 7/30

6:55 am-2:35 pm

1 stop8h 40m

Chicago Midway

Sun 8/2

10:20 am-5:54 pm

1 stop6h 34m

$398

LondonChicago

YXU - MDW

YXUMDW

London

Tue 8/4

8:40 pm-9:59 am

2 stops14h 19m

Chicago Midway

Tue 8/11

1:25 pm-5:20 am

2 stops14h 55m

$1,061

LondonChicago

YXU - MDW

YXUMDW

London

Fri 8/21

8:40 pm-6:01 pm

2 stops22h 21m

Chicago Midway

Tue 8/25

9:59 am-5:20 am

2 stops18h 21m

$1,308

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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Region of Ontario, with most prices found around $82. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Region of Ontario during the month February is also very affordable. Most momondo users find prices during this month for around $114.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Region of Ontario. The lowest ticket price found for a Tuesday 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, Friday 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 $335.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $272 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $337. 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 Region of Ontario to Chicago Midway Airport flights?

There are 2 cabin classes 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

$133

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 $133. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is $214.
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 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 $163Free CancellationRating
7.9
442 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

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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.

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