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 43% 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.

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

Air Transat, Porter Airlines, and United 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 Toronto to Chicago O'Hare Intl Airport is 1h 55m on average, while flying from Ottawa to Chicago O'Hare Intl Airport is 2h 08m 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 97 per day as of April 2026. The most frequent departure time is 1:00PM, with 43% of daily flights leaving in the afternoon.

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

As of April 2026, 679 flights take off from Region of Ontario and land in Chicago each week. The most common flight departure day for this route is Fri, 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 April 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.

$124 Cheap Flights from Ontario to Chicago in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

8:55 am - 9:45 am

YTZ

MDW

1h 50mnonstop

10:30 am - 1:10 pm

MDW

YTZ

1h 40mnonstop

$204Porter Airlines

Wed, May 13 - Sun, May 17

8:50 am - 9:50 am

YYZ

ORD

2h 00mnonstop

7:09 am - 9:54 am

ORD

YYZ

1h 45mnonstop

$206Lufthansa

Thu, Jun 4 - Sun, Jun 7

1:45 pm - 2:35 pm

YTZ

MDW

1h 50mnonstop

10:30 am - 1:10 pm

MDW

YTZ

1h 40mnonstop

$206Porter Airlines

Tue, May 5 - Fri, May 8

3:00 pm - 8:08 pm

YYZ

ORD

6h 08m

1 stop

9:55 am - 12:35 pm

ORD

YYZ

1h 40mnonstop

$208Air Canada

Sat, May 9 - Tue, May 12

10:45 am - 2:53 pm

YTZ

ORD

5h 08m

1 stop

8:45 am - 3:52 pm

ORD

YTZ

6h 07m

1 stop

$208Air Canada

Tue, May 5 - Sat, May 9

7:20 am - 8:30 am

YYZ

ORD

2h 10mnonstop

4:45 pm - 10:30 pm

ORD

YYZ

4h 45m

1 stop

$209American Airlines

Sat, Jun 6 - Sat, Jun 20

2:20 pm - 6:33 pm

YYZ

MDW

5h 13m

1 stop

6:35 pm - 11:02 pm

MDW

YYZ

3h 27m

1 stop

$220KLM

Sat, Jun 6 - Sat, Jun 13

2:20 pm - 6:33 pm

YYZ

MDW

5h 13m

1 stop

6:36 pm - 10:59 pm

MDW

YYZ

3h 23m

1 stop

$234Delta

Mon, May 11 - Sat, May 16

6:10 am - 8:43 am

YYZ

MDW

3h 33m

1 stop

9:22 am - 5:21 pm

MDW

YYZ

6h 59m

1 stop

$235Delta

Wed, May 27 - Sat, Jun 6

8:40 am - 2:17 pm

YOW

ORD

6h 37m

1 stop

8:08 am - 2:55 pm

ORD

YOW

5h 47m

1 stop

$417American Airlines

Fri, May 29 - Sun, May 31

American Airlines flights from Region of Ontario to Chicago

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

American Airlines

Jun 6

YYZ3:13 pmToronto Pearson Intl

2h 05m

ORD4:18 pmChicago O'Hare Intl

Jun 13

ORD1:19 pmChicago O'Hare Intl

8h 11m

1 stop

YYZ10:30 pmToronto Pearson Intl

$209

American Airlines

Jun 10

YYZ11:39 amToronto Pearson Intl

2h 05m

ORD12:44 pmChicago O'Hare Intl

Jun 13

ORD1:19 pmChicago O'Hare Intl

8h 11m

1 stop

YYZ10:30 pmToronto Pearson Intl

$233

American Airlines

May 28

YYZ3:45 pmToronto Pearson Intl

6h 52m

1 stop

ORD9:37 pmChicago O'Hare Intl

May 31

ORD8:08 amChicago O'Hare Intl

1h 51m

YYZ10:59 amToronto Pearson Intl

$239

United Airlines flights from Region of Ontario to Chicago

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

United Airlines

May 5

YYZ1:00 pmToronto Pearson Intl

2h 01m

ORD2:01 pmChicago O'Hare Intl

Jun 30

ORD7:09 amChicago O'Hare Intl

1h 45m

YYZ9:54 amToronto Pearson Intl

$215

United Airlines

May 9

YYZ3:00 pmToronto Pearson Intl

7h 40m

1 stop

ORD9:40 pmChicago O'Hare Intl

May 12

ORD5:00 amChicago O'Hare Intl

5h 43m

1 stop

YYZ11:43 amToronto Pearson Intl

$225

United Airlines

May 8

YYZ2:45 pmToronto Pearson Intl

1h 58m

ORD3:43 pmChicago O'Hare Intl

May 10

ORD1:01 pmChicago O'Hare Intl

1h 45m

YYZ3:46 pmToronto Pearson Intl

$228

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/13

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Sun 5/17

10:30 am-1:10 pm

Nonstop1h 40m

$204

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/4

8:50 am-9:50 am

Nonstop2h 00m

Chicago O'Hare Intl

Sun 6/7

7:09 am-9:54 am

Nonstop1h 45m

$206

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/5

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Fri 5/8

10:30 am-1:10 pm

Nonstop1h 40m

$206

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 5/9

3:00 pm-8:08 pm

1 stop6h 08m

Chicago O'Hare Intl

Tue 5/12

9:55 am-12:35 pm

Nonstop1h 40m

$208

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 5/5

10:45 am-2:53 pm

1 stop5h 08m

Chicago O'Hare Intl

Sat 5/9

8:45 am-3:52 pm

1 stop6h 07m

$208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

7:20 am-8:30 am

Nonstop2h 10m

Chicago O'Hare Intl

Sat 6/20

4:45 pm-10:30 pm

1 stop4h 45m

$209

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 6/6

2:20 pm-6:33 pm

1 stop5h 13m

Chicago Midway

Sat 6/13

6:35 pm-11:02 pm

1 stop3h 27m

$220

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/11

2:20 pm-6:33 pm

1 stop5h 13m

Chicago Midway

Sat 5/16

6:36 pm-10:59 pm

1 stop3h 23m

$234

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/27

6:10 am-8:43 am

1 stop3h 33m

Chicago Midway

Sat 6/6

9:22 am-5:21 pm

1 stop6h 59m

$235

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 5/29

8:40 am-2:17 pm

1 stop6h 37m

Chicago O'Hare Intl

Sun 5/31

8:08 am-2:55 pm

1 stop5h 47m

$417

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 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 $433. 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 $687.

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 $397. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $661.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago O'Hare Intl 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 $294 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 $195 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	$102
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 $102. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is $178.

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 April 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 (14.85% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (12.67%), Boeing 737 MAX 8 (11.52%), and Embraer 175 (9.34%).

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
Porter Airlines	PriceFrom $80	Free Cancellation	Rating 8.0 435 reviews	Search Porter Airlines flights
Air Canada	PriceFrom $146	Free Cancellation	Rating 7.1 10,966 reviews	Search Air Canada flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 9,650 reviews	Search United Airlines flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.1 11,671 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Mon 5/25

Mon 6/1

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Ontario

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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 5/8. 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

American Airlines flights from Region of Ontario to Chicago

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

United Airlines flights from Region of Ontario to Chicago

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

momondo Fare Finder

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

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.

Popular cities in the United States

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

Fly to other destinations from Ontario

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year