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 40% 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 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 Toronto to Chicago O'Hare Intl Airport is 1h 52m on average, while flying from Ottawa to Chicago O'Hare Intl Airport is 2h 19m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

Porter Airlines, United Airlines, and Delta are the most popular carriers operating from Ontario to Chicago

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

As of June 2026, 805 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 15% of weekly flights taking off on this day.

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 115 per day as of June 2026. The most frequent departure time is 1:00PM, with 43% of daily flights leaving at noon.

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 June 2026.

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.

$135 Cheap Flights from Ontario to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:55 pm - 7:52 pm

YYZ

ORD

1h 57mnonstop

8:40 pm - 11:25 pm

ORD

YYZ

1h 45mnonstop

$206Air Canada

Fri, Sep 4 - Sun, Sep 6

8:50 am - 9:40 am

YTZ

MDW

1h 50mnonstop

3:20 pm - 6:00 pm

MDW

YTZ

1h 40mnonstop

$206Porter Airlines

Sun, Jun 28 - Thu, Jul 2

7:25 pm - 8:29 pm

YTZ

ORD

2h 04mnonstop

7:25 am - 10:07 am

ORD

YTZ

1h 42mnonstop

$206Air Canada

Sun, Jul 26 - Sun, Aug 2

11:00 am - 12:00 pm

YYZ

ORD

2h 00mnonstop

7:09 am - 9:54 am

ORD

YYZ

1h 45mnonstop

$207United Airlines

Fri, Oct 2 - Mon, Oct 5

12:15 pm - 6:31 pm

YYZ

MDW

7h 16m

1 stop

9:30 am - 5:20 pm

MDW

YYZ

6h 50m

1 stop

$240Delta

Fri, Sep 11 - Mon, Sep 14

6:10 am - 9:13 am

YYZ

MDW

4h 03m

1 stop

9:19 am - 5:24 pm

MDW

YYZ

7h 05m

1 stop

$243KLM

Wed, Jul 15 - Wed, Jul 22

12:09 pm - 6:25 pm

YYZ

MDW

7h 16m

1 stop

9:19 am - 5:24 pm

MDW

YYZ

7h 05m

1 stop

$244Delta

Fri, Jul 10 - Tue, Jul 28

6:05 am - 9:14 am

YYZ

MDW

4h 09m

1 stop

9:19 am - 5:24 pm

MDW

YYZ

7h 05m

1 stop

$253Multiple Airlines

Thu, Jul 2 - Wed, Jul 8

8:40 am - 1:22 pm

YUL

ORD

5h 42m

2 stops

3:20 pm - 8:10 pm

ORD

YUL

3h 50m

1 stop

$291Multiple Airlines

Fri, Sep 4 - Tue, Sep 8

9:45 am - 11:21 am

YUL

ORD

2h 36mnonstop

8:45 am - 2:40 pm

ORD

YUL

4h 55m

1 stop

$293United Airlines

Thu, Sep 3 - Sun, Sep 6

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Air Canada flights from Region of Ontario to Chicago

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

Air Canada

Sep 4

YYZ6:55 pmToronto Pearson Intl

1h 57m

ORD7:52 pmChicago O'Hare Intl

Sep 6

ORD8:40 pmChicago O'Hare Intl

1h 45m

YYZ11:25 pmToronto Pearson Intl

$206

Air Canada

Sep 18

YTZ12:20 pmToronto Island

8h 52m

2 stops

ORD8:12 pmChicago O'Hare Intl

Sep 21

ORD8:45 amChicago O'Hare Intl

6h 05m

1 stop

YTZ3:50 pmToronto Island

$207

Air Canada

Jun 25

YYZ2:00 pmToronto Pearson Intl

1h 55m

ORD2:55 pmChicago O'Hare Intl

Jun 28

ORD3:45 pmChicago O'Hare Intl

1h 46m

YYZ6:31 pmToronto Pearson Intl

$208

Delta flights from Region of Ontario to Chicago

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

Delta

Oct 8

YYZ6:00 amToronto Pearson Intl

7h 37m

1 stop

ORD12:37 pmChicago O'Hare Intl

Oct 11

ORD7:05 amChicago O'Hare Intl

7h 14m

1 stop

YYZ3:19 pmToronto Pearson Intl

$240

Delta

Jul 10

YYZ12:09 pmToronto Pearson Intl

7h 20m

1 stop

ORD6:29 pmChicago O'Hare Intl

Jul 31

ORD5:18 pmChicago O'Hare Intl

4h 44m

1 stop

YYZ11:02 pmToronto Pearson Intl

$244

Delta

Jun 24

YYZ2:29 pmToronto Pearson Intl

7h 02m

1 stop

ORD8:31 pmChicago O'Hare Intl

Jun 27

ORD7:01 amChicago O'Hare Intl

7h 18m

1 stop

YYZ3:19 pmToronto Pearson Intl

$252

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 9/4

6:55 pm-7:52 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/6

8:40 pm-11:25 pm

Nonstop1h 45m

$206

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 6/28

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Thu 7/2

3:20 pm-6:00 pm

Nonstop1h 40m

$206

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 7/26

7:25 pm-8:29 pm

Nonstop2h 04m

Chicago O'Hare Intl

Sun 8/2

7:25 am-10:07 am

Nonstop1h 42m

$206

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/2

11:00 am-12:00 pm

Nonstop2h 00m

Chicago O'Hare Intl

Mon 10/5

7:09 am-9:54 am

Nonstop1h 45m

$207

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/11

12:15 pm-6:31 pm

1 stop7h 16m

Chicago Midway

Mon 9/14

9:30 am-5:20 pm

1 stop6h 50m

$240

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 7/15

6:10 am-9:13 am

1 stop4h 03m

Chicago Midway

Wed 7/22

9:19 am-5:24 pm

1 stop7h 05m

$243

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 7/10

12:09 pm-6:25 pm

1 stop7h 16m

Chicago Midway

Tue 7/28

9:19 am-5:24 pm

1 stop7h 05m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 7/2

6:05 am-9:14 am

1 stop4h 09m

Chicago Midway

Wed 7/8

9:19 am-5:24 pm

1 stop7h 05m

$253

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 9/4

8:40 am-1:22 pm

2 stops5h 42m

Chicago O'Hare Intl

Tue 9/8

3:20 pm-8:10 pm

1 stop3h 50m

$291

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/3

9:45 am-11:21 am

Nonstop2h 36m

Chicago O'Hare Intl

Sun 9/6

8:45 am-2:40 pm

1 stop4h 55m

$293

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 August is, on average, the cheapest month to fly to Chicago from Region of Ontario, with most prices found around $244. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Region of Ontario to Chicago during September average around $259.

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 $437. 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 $699.

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 $384. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $701.

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 from Ontario 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 $303 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 $175 on momondo.

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

There are 4 cabin classes available to choose from on Region of 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	$134
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is $134. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is $217.

The fastest flight from Region of Ontario to Chicago takes 1h 50m

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

There are 3 airports in Chicago. From Region of Ontario there are direct flights to Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Ontario to Chicago

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 June 2026.
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 (16.86% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (10.67%), Boeing 737 MAX 8 (7.26%), and Boeing 737-800 (7.25%).

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 $153	Free Cancellation	Rating 7.1 11,194 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $163	Free Cancellation	Rating 8.0 438 reviews	Search Porter Airlines flights
United Airlines	PriceFrom $187	Free Cancellation	Rating 7.4 9,828 reviews	Search United Airlines flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.1 11,661 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Portage

Saint Joseph

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?

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.

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Cheap flights from Ontario to Chicago from $135

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 7/2. 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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Air Canada flights from Region of Ontario to Chicago

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

Delta flights from Region of Ontario to Chicago

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

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

What is the cheapest month to fly to Chicago?

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?

What is the cheapest Ontario to Chicago flight route?

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

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

Can stopping save me money on Region of Ontario to Chicago flights?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying from 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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