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Cheap flights from Ontario to Chicago from C$ 149

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
1 Jul — 8 Jul1
1 adult

Cheap flight deals from Ontario to Chicago

Keep the following information in mind while searching for Ontario to Chicago flight deals. Data was last updated 26 June 2025.

Round-trip from

C$ 220

One-way from

C$ 149

Popular in

December

Cheapest in

April

Average price

C$ 347

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 155 or less
Porter Airlines
  • Porter Airlines
  • 7/8-10/8
  • Nonstop
  • 3h 30m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/7
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Ontario to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Ontario to Chicago (CHI).
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Find flight deals from Ontario to Chicago

Cheapest flights from Ontario to Chicago
Explore the most affordable flight options available from Ontario to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 June 2025.

Thu 7/87:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 10/89:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 25/6C$ 220
Wed 12/119:00 p.m.YYZ - ORD
Nonstop1h 59mLufthansa
Fri 14/116:20 p.m.ORD - YYZ
1 stop4h 26mLufthansa
Deal found 24/6C$ 223
Sat 9/86:15 a.m.YYZ - ORD
1 stop4h 37mAir Canada
Sat 16/810:40 a.m.ORD - YYZ
1 stop5h 25mAir Canada
Deal found 25/6C$ 231
Fri 22/88:25 a.m.YTZ - ORD
1 stop7h 30mAir Canada
Mon 25/810:40 a.m.ORD - YTZ
1 stop5h 06mAir Canada
Deal found 23/6C$ 232
Fri 12/91:00 p.m.YYZ - ORD
Nonstop2h 01mUnited Airlines
Tue 16/98:55 a.m.ORD - YYZ
Nonstop1h 54mUnited Airlines
Deal found 25/6C$ 234
Sun 2/115:15 p.m.YYZ - ORD
1 stop5h 50mAmerican Airlines
Tue 4/118:05 a.m.ORD - YYZ
1 stop7h 29mAmerican Airlines
Deal found 25/6C$ 253
Wed 6/86:30 a.m.YYZ - ORD
1 stop7h 20mWestJet
Sun 10/86:00 a.m.ORD - YYZ
1 stop4h 59mWestJet
Deal found 23/6C$ 257
Mon 21/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 27/79:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 24/6C$ 258
Wed 20/812:48 p.m.YYZ - MDW
1 stop5h 49mWestJet
Sat 23/810:31 a.m.MDW - YYZ
1 stop5h 26mWestJet
Deal found 25/6C$ 263
Thu 7/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 14/85:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 25/6C$ 273
Wed 10/92:50 p.m.YYZ - MDW
1 stop4h 47mDelta
Sat 13/95:59 p.m.MDW - YYZ
1 stop3h 59mDelta
Deal found 26/6C$ 291
Thu 4/97:55 a.m.YYZ - ORD
1 stop6h 14mDelta
Sun 7/97:15 a.m.ORD - YYZ
1 stop3h 05mDelta
Deal found 24/6C$ 301

Cheapflights Fare Finder

Customize your flight search to find flights from Ontario to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 26 June 2025.
Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

Fly from

Ontario

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 10/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/11

9:00 p.m.-9:59 p.m.

Nonstop1h 59m

Chicago O'Hare Intl

Fri 14/11

6:20 p.m.-11:46 p.m.

1 stop4h 26m

C$ 223

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 9/8

6:15 a.m.-9:52 a.m.

1 stop4h 37m

Chicago O'Hare Intl

Sat 16/8

10:40 a.m.-5:05 p.m.

1 stop5h 25m

C$ 231

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 22/8

8:25 a.m.-2:55 p.m.

1 stop7h 30m

Chicago O'Hare Intl

Mon 25/8

10:40 a.m.-4:46 p.m.

1 stop5h 06m

C$ 232

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/9

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Tue 16/9

8:55 a.m.-11:49 a.m.

Nonstop1h 54m

C$ 234

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 2/11

5:15 p.m.-10:05 p.m.

1 stop5h 50m

Chicago O'Hare Intl

Tue 4/11

8:05 a.m.-4:34 p.m.

1 stop7h 29m

C$ 253

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 6/8

6:30 a.m.-12:50 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Sun 10/8

6:00 a.m.-11:59 a.m.

1 stop4h 59m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 27/7

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 258

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 20/8

12:48 p.m.-5:37 p.m.

1 stop5h 49m

Chicago Midway

Sat 23/8

10:31 a.m.-4:57 p.m.

1 stop5h 26m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 9/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sat 16/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 275

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/6

Showing 1-10 of 60 results
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Best time to book a flight from Ontario to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Ontario with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Ontario to Chicago

What is the cheapest month to book a flight from Region of Ontario to Chicago?

Currently, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 261). Flying from Region of Ontario to Chicago in March is currently the most expensive (average of C$ 351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ON to CHI?

Find hourly flight availability from Ontario to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 26 June 2025.

When flying from Region of Ontario to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Region of Ontario to Chicago

Explore weekly flight availability from Ontario to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 26 June 2025.

The most flights from CAON to CHI are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

How much does it cost to fly round-trip from Region of Ontario to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 26 June 2025.
Read through reviews of airlines operating flights from Ontario to Chicago, such as Porter Airlines,Delta, andAir Transat. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
295 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
295 reviews
Porter Airlines
8.0
Very good
295 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,963 reviews
Porter Airlines
8.0
Very good
295 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
401 reviews
Porter Airlines
8.0
Very good
295 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,838 reviews
Porter Airlines
8.0
Very good
295 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Virgin Atlantic
7.4
Good
654 reviews
Porter Airlines
8.0
Very good
295 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Related info for your journey

Find useful and relevant information for your journey from Ontario to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Region of Ontario to Chicago one-way?

    The cheapest airline one-way is Porter Airlines, with whom users have recently found tickets for as low as C$ 149. However, be on the lookout for offers from American Airlines and Air Canada, as they are both options that can get you from Region of Ontario to Chicago for a low price.

  • What are the most popular routes from Region of Ontario to Chicago?

    When deciding which route to take from Region of Ontario to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Region of Ontario to Chicago?

    No one likes to see their flight delayed. When booking a flight from Region of Ontario to Chicago consider choosing Copa Airlines (96%), SkyWest Airlines (93%) or ANA (93%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Region of Ontario to Chicago?

    On average you can expect to pay C$ 1,353 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 187 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 198.

  • Can I find deals for flights from Ontario to Chicago that include hotel bookings?

    Yes. In addition to deals on Ontario to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Ontario to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Ontario to Chicago.

  • Can I find deals for business class flights from Ontario to Chicago?

    Yes. Cheapflights offers flight deals from Ontario to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Region of Ontario to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 261). Flying from Region of Ontario to Chicago in March is currently the most expensive (average of C$ 351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Ontario to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
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Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
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Top 5 airlines flying from Ontario to Chicago

Discover the top 5 airlines that operate flights from Ontario to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 26 June 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 222AverageC$ 504FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 231AverageC$ 375FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 279AverageC$ 495FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 294AverageC$ 562FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 423AverageC$ 610FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Ontario to Chicago?

When you search for this flight from Ontario to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Ontario to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Ontario.

Can Cheapflights find flights from Ontario to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Ontario shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Ontario to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Ontario to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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