What is the cheapest airline that flies from Ontario to Chicago?

Porter Airlines, Air Canada, and WestJet are the most popular carriers operating from Ontario to Chicago

How many flights depart from Region of Ontario to Chicago on average per day?

The number of flights available between Region of Ontario and Chicago is 102 per day as of September 2025. The most frequent departure time is 6:00AM, with 46% of daily flights leaving at noon.

How long does it take to fly to Chicago?

Average flight duration from Region of Ontario to Chicago depends on which airport you fly into and out of. Flying from Ottawa to Chicago O'Hare Intl Airport is 2h 08m on average, while flying from Toronto to Chicago O'Hare Intl Airport is 3h 26m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How many flights depart from Region of Ontario to Chicago on average per week?

As of September 2025, 718 flights take off from Region of Ontario and land in Chicago each week. The most common flight departure day for this route is Thu, with 15% of weekly flights taking off on this day.

What airlines fly to Chicago?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Region of Ontario according to our data. Air Canada is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Ontario to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Ontario to Chicago?

The number of operators available for flights from Ontario to Chicago is 4 as of September 2025.

How old do you have to be to fly from Ontario to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Ontario to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$134 Cheap Flights from Ontario to Chicago in 2025/26

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Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:30 am - 6:38 pmYYZ-ORD

13h 08m1 stop

7:43 pm - 2:05 pmORD-YYZ

17h 22m1 stop

$215Multiple Airlines

Find Deal

Wed, Oct 15 - Wed, Oct 22

4:00 pm - 11:44 pmYYZ-ORD

8h 44m1 stop

1:26 pm - 9:07 pmORD-YYZ

6h 41m1 stop

$217Multiple Airlines

Find Deal

Mon, Oct 20 - Thu, Oct 23

12:25 pm - 6:49 pmYYZ-ORD

7h 24m1 stop

7:10 am - 11:20 amORD-YYZ

3h 10m1 stop

$241WestJet

Find Deal

Sat, Nov 1 - Sat, Nov 8

6:20 am - 10:30 amYYZ-MDW

5h 10m1 stop

3:00 pm - 11:18 pmMDW-YYZ

7h 18m1 stop

$241WestJet

Find Deal

Sat, Nov 1 - Sat, Nov 8

6:15 pm - 8:00 pmYUL-ORD

2h 45mnonstop

12:50 pm - 3:57 pmORD-YUL

2h 07mnonstop

$244Air Canada

Find Deal

Sat, Nov 1 - Sat, Nov 8

1:10 pm - 4:24 pmYUL-MDW

4h 14m1 stop

9:35 am - 4:00 pmMDW-YUL

5h 25m1 stop

$245Porter Airlines

Find Deal

Fri, Oct 17 - Wed, Oct 22

1:10 pm - 4:24 pmYUL-MDW

4h 14m1 stop

9:35 am - 4:00 pmMDW-YUL

5h 25m1 stop

$246Porter Airlines

Find Deal

Wed, Oct 8 - Thu, Oct 16

6:15 pm - 8:00 pmYUL-ORD

2h 45mnonstop

12:50 pm - 3:57 pmORD-YUL

2h 07mnonstop

$250Air Canada

Find Deal

Fri, Oct 31 - Fri, Nov 7

6:00 am - 8:00 amYUL-ORD

3h 00mnonstop

5:55 pm - 9:17 pmORD-YUL

2h 22mnonstop

$260United Airlines

Find Deal

Sat, Nov 22 - Sat, Nov 29

4:55 pm - 6:41 pmYUL-ORD

2h 46mnonstop

2:08 pm - 5:26 pmORD-YUL

2h 18mnonstop

$263United Airlines

Find Deal

Thu, Oct 9 - Sun, Oct 12

WestJet flights from Region of Ontario to Chicago

Our best WestJet deals on Region of Ontario to Chicago flight tickets

WestJet

Nov 1

YYZ12:25 pmToronto Pearson Intl

7h 24m

1 stop

ORD6:49 pmChicago O'Hare Intl

Nov 8

ORD7:10 amChicago O'Hare Intl

3h 10m

1 stop

YYZ11:20 amToronto Pearson Intl

$241

Find similar

WestJet

Oct 17

YYZ8:00 amToronto Pearson Intl

9h 43m

1 stop

ORD4:43 pmChicago O'Hare Intl

Oct 19

ORD5:30 pmChicago O'Hare Intl

12h 17m

2 stops

YYZ6:47 amToronto Pearson Intl

$243

Find similar

WestJet

Oct 24

YYZ8:00 amToronto Pearson Intl

9h 43m

1 stop

ORD4:43 pmChicago O'Hare Intl

Oct 30

ORD2:20 pmChicago O'Hare Intl

9h 06m

1 stop

YYZ12:26 amToronto Pearson Intl

$246

Find similar

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

Air Canada

Nov 1

YUL6:15 pmMontreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 pmChicago O'Hare Intl

Nov 8

ORD12:50 pmChicago O'Hare Intl

2h 07m

YUL3:57 pmMontreal Pierre Elliott Trudeau Intl

$244

Find similar

Air Canada

Oct 31

YUL6:15 pmMontreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 pmChicago O'Hare Intl

Nov 7

ORD12:50 pmChicago O'Hare Intl

2h 07m

YUL3:57 pmMontreal Pierre Elliott Trudeau Intl

$250

Find similar

Air Canada

Nov 1

YUL6:15 pmMontreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 pmChicago O'Hare Intl

Nov 8

ORD3:55 pmChicago O'Hare Intl

4h 57m

1 stop

YUL9:52 pmMontreal Pierre Elliott Trudeau Intl

$256

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/15

6:30 am-6:38 pm

1 stop13h 08m

Chicago O'Hare Intl

Wed 10/22

7:43 pm-2:05 pm

1 stop17h 22m

$215

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/20

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Thu 10/23

1:26 pm-9:07 pm

1 stop6h 41m

$217

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/1

12:25 pm-6:49 pm

1 stop7h 24m

Chicago O'Hare Intl

Sat 11/8

7:10 am-11:20 am

1 stop3h 10m

$241

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

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 11/1

6:15 pm-8:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sat 11/8

12:50 pm-3:57 pm

Nonstop2h 07m

$244

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Wed 10/22

9:35 am-4:00 pm

1 stop5h 25m

$245

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 10/8

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Thu 10/16

9:35 am-4:00 pm

1 stop5h 25m

$246

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 10/31

6:15 pm-8:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Fri 11/7

12:50 pm-3:57 pm

Nonstop2h 07m

$250

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 11/22

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 11/29

5:55 pm-9:17 pm

Nonstop2h 22m

$260

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 10/9

4:55 pm-6:41 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sun 10/12

2:08 pm-5:26 pm

Nonstop2h 18m

$263

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How to get the cheapest flight ticket from Region of Ontario to Chicago

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

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Region of Ontario, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Region of Ontario to Chicago during June average around $225.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $396. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Region of Ontario to Chicago for around $621.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Region of Ontario to Chicago during this time can be as low as $391. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $292 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Region of Ontario for as low as $216 on momondo.

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago 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 flights?

You could potentially save up to 12% on your flight if you consider stops on a Region of Ontario to Chicago flight.

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best Price Found	$179
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is $179. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is $181.

The fastest flight from Region of Ontario to Chicago takes 1h 49m

Direct flights go from Region of Ontario to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Ontario to Chicago?
Prices for flights from Ontario to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Ontario to Chicago?
The number of operators available for flights from Ontario to Chicago is 4 as of September 2025.
How old do you have to be to fly from Ontario to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Ontario to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Region of Ontario to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Region of Ontario to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q (19.39% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (15.55%), Boeing 737-800 (12.07%), and Embraer 175 (7.98%).

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $146	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $158	Free Cancellation	Rating 7.9 365 reviews	Search Porter Airlines flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
American Airlines	PriceFrom $196	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

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?

Flights from Ontario to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Ontario to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Ontario to Chicago.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Ontario. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Denverfrom $63

Cheap flights from Ontario to Chicago from $134

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 10/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

WestJet flights from Region of Ontario to Chicago

Our best WestJet deals on Region of Ontario to Chicago flight tickets

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

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Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Region of Ontario to Chicago

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?

The month of July is, on average, the cheapest month to fly to Chicago from Region of Ontario, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Region of Ontario to Chicago during June average around $225.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Region of Ontario to Chicago during this time can be as low as $391. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago 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 flights?

You could potentially save up to 12% on your flight if you consider stops on a Region of Ontario to Chicago flight.

What is the cheapest airline that flies from Ontario to Chicago?

Porter Airlines, Air Canada, and WestJet are the most popular carriers operating from Ontario to Chicago

What airlines fly to Chicago?

How many flights depart from Region of Ontario to Chicago on average per day?

The number of flights available between Region of Ontario and Chicago is 102 per day as of September 2025. The most frequent departure time is 6:00AM, with 46% of daily flights leaving at noon.

How many flights depart from Region of Ontario to Chicago on average per week?

As of September 2025, 718 flights take off from Region of Ontario and land in Chicago each week. The most common flight departure day for this route is Thu, with 15% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

How many operators does momondo search for flights from Ontario to Chicago?

How old do you have to be to fly from Ontario to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Region of Ontario to Chicago?

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights from Ontario to Chicago?

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago