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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 10/20. 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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Cheap round-trip flights

Multiple Airlines Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$234Multiple Airlines
Find Deal
Tue, Oct 14 - Wed, Oct 22
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 am - 4:00 pmMDW-YUL
5h 25m1 stop
$234Porter Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 20
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$235Porter Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
WestJet Logo
6:20 am - 10:30 amYYZ-MDW
5h 10m1 stop
WestJet Logo
3:00 pm - 11:18 pmMDW-YYZ
7h 18m1 stop
$241WestJet
Find Deal
Sat, Nov 1 - Sat, Nov 8
Multiple Airlines Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$246Multiple Airlines
Find Deal
Tue, Oct 14 - Sun, Oct 19
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
$256WestJet
Find Deal
Tue, Oct 21 - Sat, Oct 25
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$281Air Transat
Find Deal
Sun, Oct 5 - Tue, Oct 7
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$287Air Transat
Find Deal
Sun, Nov 2 - Tue, Nov 11
Delta Logo
6:00 am - 12:28 pmYUL-MDW
7h 28m1 stop
Delta Logo
4:23 pm - 11:48 pmMDW-YUL
6h 25m1 stop
$289Delta
Find Deal
Sun, Oct 12 - Sat, Oct 25
Delta Logo
7:10 am - 1:07 pmYUL-MDW
6h 57m1 stop
Delta Logo
9:32 am - 3:55 pmMDW-YUL
5h 23m1 stop
$293Delta
Find Deal
Sat, Nov 22 - Sat, Nov 29

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
Nov 1
YYZ6:20 amToronto Pearson Intl
5h 10m
1 stop
MDW10:30 amChicago Midway
Nov 8
MDW3:00 pmChicago Midway
7h 18m
1 stop
YYZ11:18 pmToronto Pearson Intl
$241
Find similar
WestJet
Oct 21
YYZ6:00 pmToronto Pearson Intl
5h 14m
1 stop
MDW10:14 pmChicago Midway
Oct 25
MDW10:35 amChicago Midway
5h 15m
1 stop
YYZ4:50 pmToronto Pearson Intl
$256
Find similar
WestJet
Nov 1
YYZ6:20 amToronto Pearson Intl
7h 48m
1 stop
MDW1:08 pmChicago Midway
Nov 8
MDW9:20 amChicago Midway
5h 39m
1 stop
YYZ3:59 pmToronto Pearson Intl
$257
Find similar

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
Oct 17
YUL1:10 pmMontreal Pierre Elliott Trudeau Intl
4h 14m
1 stop
MDW4:24 pmChicago Midway
Oct 20
MDW9:35 amChicago Midway
5h 25m
1 stop
YUL4:00 pmMontreal Pierre Elliott Trudeau Intl
$234
Find similar
Porter Airlines
Oct 30
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 amChicago Midway
Nov 6
MDW4:15 pmChicago Midway
5h 30m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$235
Find similar
Porter Airlines
Oct 16
YUL10:45 amMontreal Pierre Elliott Trudeau Intl
6h 39m
1 stop
MDW4:24 pmChicago Midway
Oct 19
MDW5:20 pmChicago Midway
3h 55m
1 stop
YUL10:15 pmMontreal Pierre Elliott Trudeau Intl
$236
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 September 17, 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 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Wed 10/22

9:35 am-12:17 pm

Nonstop1h 42m

$234

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Mon 10/20

9:35 am-4:00 pm

1 stop5h 25m

$234

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/30

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Thu 11/6

4:15 pm-10:45 pm

1 stop5h 30m

$235

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 11/1

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

Sat 11/8

3:00 pm-11:18 pm

1 stop7h 18m

$241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Sun 10/19

9:35 am-12:17 pm

Nonstop1h 42m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 10/21

6:00 pm-10:14 pm

1 stop5h 14m

Chicago Midway

Sat 10/25

10:35 am-4:50 pm

1 stop5h 15m

$256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 10/5

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Tue 10/7

5:20 pm-8:02 pm

Nonstop1h 42m

$281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 11/2

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Tue 11/11

11:00 am-1:42 pm

Nonstop1h 42m

$287

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 10/12

6:00 am-12:28 pm

1 stop7h 28m

Chicago Midway

Sat 10/25

4:23 pm-11:48 pm

1 stop6h 25m

$289

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/22

7:10 am-1:07 pm

1 stop6h 57m

Chicago Midway

Sat 11/29

9:32 am-3:55 pm

1 stop5h 23m

$293

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 $174. 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 $289.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $120 when looking at flights departing at noon. Try not to purchase tickets in the evening 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

$179

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 $179. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is $181.
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 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
7.9
365 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
Lansing
Portage
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.

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