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Not ready to book? to track prices.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
Delta flights from Region of Ontario to Chicago Midway Airport
Our best Delta deals on Region of Ontario to Chicago Midway Airport flight tickets
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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
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Wed 10/21
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sat 10/24
11:45 am-2:25 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Fri 10/23
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Fri 10/23
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sat 10/17
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sat 10/24
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Wed 10/21
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Thu 10/22
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 10/20
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Fri 10/23
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 10/22
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Sat 10/24
11:45 am-2:25 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Fri 10/16
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Fri 10/23
11:45 am-2:25 pm
Nonstop1h 40m
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 10/20
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Fri 10/23
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 11/26
6:00 am-11:25 am
1 stop6h 25m
Chicago Midway
Mon 12/7
6:41 pm-11:07 pm
1 stop3h 26m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 11/28
12:15 pm-6:04 pm
1 stop6h 49m
Chicago Midway
Mon 12/7
6:41 pm-11:07 pm
1 stop3h 26m
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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Region of Ontario, with most prices found around $204. 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 $211.
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 $229. 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 $347.
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 $292 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $445. 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 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.
How many flights depart from Region of Ontario to Chicago Midway Airport on average per day?
As of October 2026, 4 flights take off from Region of Ontario and land in Chicago Midway Airport each day. The most common flight departure time for this route is 10:00AM, with 50% of daily flights taking off at noon.
How many flights depart from Region of Ontario to Chicago Midway Airport on average per week?
As of October 2026, there are 28 flights per week flying from Region of Ontario to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
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
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?
As of October 2026, there is 1 operator available to choose from 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?
Based on momondo bookings for flights between Region of Ontario and Chicago Midway Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 42.48% of the total bookings. Other popular models include Boeing 737-900 with 9.77%, Embraer 175 (Enhanced Winglets) with 8.52%, and Boeing 737-800 with 6.34%.
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 | ||
|---|---|---|---|---|---|
| PriceFrom $185 | Free Cancellation | Rating 8.0 466 reviews |
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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.