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

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

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 22m on average, while flying from Toronto to Chicago O'Hare Intl Airport is 3h 39m 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 day?

The number of flights available between Region of Ontario and Chicago is 94 per day as of August 2025. The most frequent departure time is 6:00AM, with 44% of daily flights leaving at noon.

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 50% 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.

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

As of August 2025, 663 flights take off from Region of Ontario and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

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 August 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.

$99 Cheap Flights from Ontario to Chicago in 2025

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Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:15 am - 9:13 amYYZ-ORD

1h 58mnonstop

2:00 pm - 4:39 pmORD-YYZ

1h 39mnonstop

$147Air Canada

Find Deal

Fri, Nov 7 - Sun, Nov 16

8:15 am - 9:15 amYYZ-ORD

2h 00mnonstop

10:00 am - 12:40 pmORD-YYZ

1h 40mnonstop

$159Air Canada

Find Deal

Fri, Oct 31 - Mon, Nov 3

4:44 pm - 5:44 pmYYZ-ORD

2h 00mnonstop

5:00 am - 11:03 amORD-YYZ

5h 03m1 stop

$169American Airlines

Find Deal

Fri, Nov 7 - Sun, Nov 16

7:50 am - 8:39 amYTZ-MDW

1h 49mnonstop

5:20 pm - 8:02 pmMDW-YTZ

1h 42mnonstop

$171Porter Airlines

Find Deal

Thu, Sep 11 - Sun, Sep 14

3:35 pm - 4:24 pmYTZ-MDW

1h 49mnonstop

5:20 pm - 8:02 pmMDW-YTZ

1h 42mnonstop

$173Porter Airlines

Find Deal

Thu, Aug 28 - Thu, Sep 4

5:30 pm - 6:39 pmYYZ-ORD

2h 09mnonstop

7:10 am - 9:58 amORD-YYZ

1h 48mnonstop

$178United Airlines

Find Deal

Fri, Nov 7 - Sun, Nov 9

11:44 am - 12:39 pmYYZ-ORD

1h 55mnonstop

11:49 am - 5:19 pmORD-YYZ

4h 30m1 stop

$180American Airlines

Find Deal

Tue, Sep 16 - Tue, Sep 23

7:40 pm - 11:43 pmYYZ-ORD

5h 03m1 stop

11:15 am - 2:01 pmORD-YYZ

1h 46mnonstop

$183United Airlines

Find Deal

Fri, Nov 7 - Sun, Nov 9

2:30 pm - 10:26 pmYYZ-ORD

8h 56m1 stop

4:56 pm - 10:55 pmORD-YYZ

4h 59m1 stop

$202Delta

Find Deal

Tue, Oct 14 - Sat, Oct 18

12:15 pm - 6:04 pmYYZ-ORD

6h 49m1 stop

6:15 am - 11:38 amORD-YYZ

4h 23m1 stop

$212Delta

Find Deal

Thu, Sep 11 - Sat, Sep 27

United Airlines flights from Region of Ontario to Chicago

Our best United Airlines deals on Region of Ontario to Chicago flight tickets

United Airlines

Nov 7

YYZ5:30 pmToronto Pearson Intl

2h 09m

ORD6:39 pmChicago O'Hare Intl

Nov 9

ORD7:10 amChicago O'Hare Intl

1h 48m

YYZ9:58 amToronto Pearson Intl

$178

Find similar

United Airlines

Nov 7

YYZ7:40 pmToronto Pearson Intl

5h 03m

1 stop

ORD11:43 pmChicago O'Hare Intl

Nov 9

ORD11:15 amChicago O'Hare Intl

1h 46m

YYZ2:01 pmToronto Pearson Intl

$183

Find similar

United Airlines

Nov 7

YYZ6:40 pmToronto Pearson Intl

5h 54m

1 stop

ORD11:34 pmChicago O'Hare Intl

Nov 9

ORD6:28 pmChicago O'Hare Intl

1h 53m

YYZ9:21 pmToronto Pearson Intl

$184

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 7

YYZ8:15 amToronto Pearson Intl

1h 58m

ORD9:13 amChicago O'Hare Intl

Nov 16

ORD2:00 pmChicago O'Hare Intl

1h 39m

YYZ4:39 pmToronto Pearson Intl

$147

Find similar

Air Canada

Oct 31

YYZ8:15 amToronto Pearson Intl

2h 00m

ORD9:15 amChicago O'Hare Intl

Nov 3

ORD10:00 amChicago O'Hare Intl

1h 40m

YYZ12:40 pmToronto Pearson Intl

$159

Find similar

Air Canada

Oct 6

YYZ4:40 pmToronto Pearson Intl

1h 53m

ORD5:33 pmChicago O'Hare Intl

Oct 8

ORD8:25 pmChicago O'Hare Intl

1h 43m

YYZ11:08 pmToronto Pearson Intl

$163

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

8:15 am-9:13 am

Nonstop1h 58m

Chicago O'Hare Intl

Sun 11/16

2:00 pm-4:39 pm

Nonstop1h 39m

$147

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/31

8:15 am-9:15 am

Nonstop2h 00m

Chicago O'Hare Intl

Mon 11/3

10:00 am-12:40 pm

Nonstop1h 40m

$159

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

4:44 pm-5:44 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 11/16

5:00 am-11:03 am

1 stop5h 03m

$169

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/11

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sun 9/14

5:20 pm-8:02 pm

Nonstop1h 42m

$171

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/28

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Thu 9/4

5:20 pm-8:02 pm

Nonstop1h 42m

$173

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

5:30 pm-6:39 pm

Nonstop2h 09m

Chicago O'Hare Intl

Sun 11/9

7:10 am-9:58 am

Nonstop1h 48m

$178

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 9/16

11:44 am-12:39 pm

Nonstop1h 55m

Chicago O'Hare Intl

Tue 9/23

11:49 am-5:19 pm

1 stop4h 30m

$180

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

7:40 pm-11:43 pm

1 stop5h 03m

Chicago O'Hare Intl

Sun 11/9

11:15 am-2:01 pm

Nonstop1h 46m

$183

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/14

2:30 pm-10:26 pm

1 stop8h 56m

Chicago O'Hare Intl

Sat 10/18

4:56 pm-10:55 pm

1 stop4h 59m

$202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/11

12:15 pm-6:04 pm

1 stop6h 49m

Chicago O'Hare Intl

Sat 9/27

6:15 am-11:38 am

1 stop4h 23m

$212

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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 June is, on average, the cheapest month to fly to Chicago from Region of Ontario, with most prices found around $224. If you’re not able to fly to Chicago in June, then April is your next best option. Flight prices from Region of Ontario to Chicago during April average around $235.

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 $384. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Region of Ontario to Chicago for around $628.

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 $359. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $558.

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 $295 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 $240 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?

No. A direct flight is the cheapest option for a flight between Region of Ontario 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	$99
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is $99. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is $147.

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

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

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), 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 August 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 (21.14% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (16.72%), Boeing 737-800 (15.16%), and Airbus A220-300 (8.64%).

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 $150	Free Cancellation	Rating 7.1 9,879 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $158	Free Cancellation	Rating 8.0 321 reviews	Search Porter Airlines flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 8,912 reviews	Search United Airlines flights
American Airlines	PriceFrom $195	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

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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Cheap flights from Ontario to Chicago from $99

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 11/2. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

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Cheap direct flights

United Airlines flights from Region of Ontario to Chicago

Our best United Airlines 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.

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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

What is the cheapest month to fly to Chicago?

The month of June is, on average, the cheapest month to fly to Chicago from Region of Ontario, with most prices found around $224. If you’re not able to fly to Chicago in June, then April is your next best option. Flight prices from Region of Ontario to Chicago during April average around $235.

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 $359. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $558.

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?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

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

Air Canada, American Airlines, and Porter Airlines 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 94 per day as of August 2025. The most frequent departure time is 6:00AM, with 44% of daily flights leaving at noon.

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

As of August 2025, 663 flights take off from Region of Ontario and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% 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