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Cheap flights from Ontario to Chicago from $124

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 5/6. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
$196Multiple Airlines
Thu, Jul 23 - Fri, Jul 24
Air Transat Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Air Transat Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$197Air Transat
Wed, May 6 - Wed, May 13
Multiple Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$198Multiple Airlines
Sat, May 2 - Tue, May 5
Porter Airlines Logo
9:25 am - 10:15 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$199Porter Airlines
Wed, Apr 22 - Sat, May 2
Air Transat Logo
9:25 am - 10:15 am
YTZ
-
MDW
1h 50mnonstop
Air Transat Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$201Air Transat
Mon, Apr 27 - Thu, May 7
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
$202Porter Airlines
Sat, Jun 27 - Mon, Jul 6
Delta Logo
12:16 pm - 5:58 pm
YYZ
-
MDW
6h 42m
1 stop
Delta Logo
1:24 pm - 10:56 pm
MDW
-
YYZ
8h 32m
1 stop
$217Delta
Sun, Apr 26 - Mon, May 4
Delta Logo
6:10 am - 12:43 pm
YYZ
-
MDW
7h 33m
1 stop
Delta Logo
9:22 am - 1:30 pm
MDW
-
YYZ
3h 08m
1 stop
$222Delta
Sat, May 2 - Tue, May 12
WestJet Logo
6:10 am - 5:56 pm
YXU
-
MDW
12h 46m
2 stops
WestJet Logo
9:22 am - 5:20 am
MDW
-
YXU
18h 58m
2 stops
$1,462WestJet
Sun, May 17 - Sun, May 24
WestJet Logo
6:10 am - 8:47 am
YXU
-
MDW
27h 37m
2 stops
WestJet Logo
9:29 am - 5:20 am
MDW
-
YXU
18h 51m
2 stops
$1,541WestJet
Thu, Apr 30 - Mon, May 4

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
Apr 26
YYZ12:16 pmToronto Pearson Intl
6h 42m
1 stop
MDW5:58 pmChicago Midway
May 9
MDW9:22 amChicago Midway
3h 08m
1 stop
YYZ1:30 pmToronto Pearson Intl
$217
Delta
May 2
YYZ6:10 amToronto Pearson Intl
7h 33m
1 stop
MDW12:43 pmChicago Midway
May 12
MDW9:22 amChicago Midway
3h 08m
1 stop
YYZ1:30 pmToronto Pearson Intl
$222
Delta
May 2
YYZ2:15 pmToronto Pearson Intl
4h 43m
1 stop
MDW5:58 pmChicago Midway
May 4
MDW6:38 pmChicago Midway
3h 18m
1 stop
YYZ10:56 pmToronto Pearson Intl
$223

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
Apr 22
YTZ9:25 amToronto Island
1h 50m
MDW10:15 amChicago Midway
May 2
MDW10:30 amChicago Midway
1h 40m
YTZ1:10 pmToronto Island
$199
Porter Airlines
Jun 27
YTZ8:50 amToronto Island
1h 50m
MDW9:40 amChicago Midway
Jul 6
MDW10:25 amChicago Midway
1h 40m
YTZ1:05 pmToronto Island
$202
Porter Airlines
Jul 13
YTZ8:50 amToronto Island
1h 50m
MDW9:40 amChicago Midway
Jul 21
MDW3:20 pmChicago Midway
1h 40m
YTZ6:00 pmToronto Island
$207

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 April 2, 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

Thu 7/23

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Fri 7/24

10:25 am-1:05 pm

Nonstop1h 40m

$196

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/6

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Wed 5/13

3:20 pm-6:00 pm

Nonstop1h 40m

$197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 5/2

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Tue 5/5

10:30 am-1:10 pm

Nonstop1h 40m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/22

9:25 am-10:15 am

Nonstop1h 50m

Chicago Midway

Sat 5/2

10:30 am-1:10 pm

Nonstop1h 40m

$199

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 4/27

9:25 am-10:15 am

Nonstop1h 50m

Chicago Midway

Thu 5/7

10:30 am-1:10 pm

Nonstop1h 40m

$201

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 6/27

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Mon 7/6

10:25 am-1:05 pm

Nonstop1h 40m

$202

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 4/26

12:16 pm-5:58 pm

1 stop6h 42m

Chicago Midway

Mon 5/4

1:24 pm-10:56 pm

1 stop8h 32m

$217

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 5/2

6:10 am-12:43 pm

1 stop7h 33m

Chicago Midway

Tue 5/12

9:22 am-1:30 pm

1 stop3h 08m

$222

LondonChicago

YXU - MDW

YXUMDW

London

Sun 5/17

6:10 am-5:56 pm

2 stops12h 46m

Chicago Midway

Sun 5/24

9:22 am-5:20 am

2 stops18h 58m

$1,462

LondonChicago

YXU - MDW

YXUMDW

London

Thu 4/30

6:10 am-8:47 am

2 stops27h 37m

Chicago Midway

Mon 5/4

9:29 am-5:20 am

2 stops18h 51m

$1,541

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 January is also very affordable. Most momondo users find prices during this month for around $192.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Region of Ontario. The lowest ticket price found for a Wednesday departure recently was $215. 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 $302.

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 $239 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $320. 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 2 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

$127

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 $127. The best round-trip flight deal from Region of Ontario to Chicago Midway Airport found on momondo in the last 72 hours is $291.
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 $80Free CancellationRating
8.0
430 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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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