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Cheap flights from Ontario to Chicago from C$ 148

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
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 220

One-way from

C$ 148

Popular in

December

Cheapest in

April

Average price

C$ 346

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 26/6-29/6
  • Nonstop
  • 3h 32m 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$ 40 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).
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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 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 29/69:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/6C$ 220
Wed 10/98:15 a.m.YYZ - ORD
Nonstop1h 53mAir Canada
Fri 12/96:20 p.m.ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 12/6C$ 226
Thu 4/92:30 p.m.YYZ - ORD
1 stop6h 18mUnited Airlines
Wed 10/97:15 a.m.ORD - YYZ
1 stop5h 32mUnited Airlines
Deal found 10/6C$ 235
Sat 30/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 12/99:15 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/6C$ 254
Tue 30/93:45 p.m.YYZ - ORD
1 stop5h 42mAmerican Airlines
Thu 2/109:48 a.m.ORD - YYZ
1 stop6h 27mAmerican Airlines
Deal found 10/6C$ 261
Mon 18/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 19/85:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 11/6C$ 280
Sat 4/1010:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Wed 15/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 12/6C$ 283
Thu 3/77:00 a.m.YYZ - ORD
Nonstop1h 59mLufthansa
Mon 7/79:14 p.m.ORD - YYZ
Nonstop1h 44mLufthansa
Deal found 11/6C$ 286
Sun 12/1012:15 p.m.YYZ - ORD
1 stop7h 23mDelta
Sat 18/105:45 p.m.ORD - YYZ
1 stop4h 13mDelta
Deal found 11/6C$ 291
Sat 4/1012:15 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/109:30 a.m.MDW - YYZ
1 stop6h 53mDelta
Deal found 11/6C$ 291
Fri 11/71:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 13/79:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 10/6C$ 309
Wed 27/81:20 p.m.YUL - ORD
Nonstop2h 35mAir Canada
Wed 3/98:40 a.m.ORD - YUL
Nonstop2h 17mAir Canada
Deal found 10/6C$ 310

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 12 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 26/6

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

Nonstop1h 50m

Chicago Midway

Sun 29/6

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/9

8:15 a.m.-9:08 a.m.

Nonstop1h 53m

Chicago O'Hare Intl

Fri 12/9

6:20 p.m.-9:02 p.m.

Nonstop1h 42m

C$ 226

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/9

2:30 p.m.-7:48 p.m.

1 stop6h 18m

Chicago O'Hare Intl

Wed 10/9

7:15 a.m.-1:47 p.m.

1 stop5h 32m

C$ 235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/9

3:45 p.m.-8:27 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Thu 2/10

9:48 a.m.-5:15 p.m.

1 stop6h 27m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

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

Nonstop1h 50m

Chicago Midway

Mon 30/6

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

Nonstop1h 40m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/8

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

Nonstop1h 50m

Chicago Midway

Tue 19/8

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

10:25 a.m.-2:55 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Wed 15/10

10:40 a.m.-4:45 p.m.

1 stop5h 05m

C$ 283

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 3/7

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Mon 7/7

9:14 p.m.-11:58 p.m.

Nonstop1h 44m

C$ 286

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

12:15 p.m.-6:38 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Sat 18/10

5:45 p.m.-10:58 p.m.

1 stop4h 13m

C$ 291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 291

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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$ 352). 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 12 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 12 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 (33 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 12 June 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta and KLM from Ontario to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.7

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
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.7

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
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.7

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!!!
KLM
7.8
Good
1,358 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.7

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
396 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.7

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
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.7

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$ 148. However, be on the lookout for offers from United 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 Toronto Pearson Intl - Chicago Midway 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 SkyWest Airlines (98%), Republic Airways (92%) or Copa Airlines (91%) 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$ 2,717 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 180 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 201.

  • 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$ 352). 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.
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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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 232AverageC$ 390FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 278AverageC$ 512FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 283AverageC$ 494FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 302AverageC$ 568FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 423AverageC$ 631FlexibilityNo 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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