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Cheap flights from Ontario to Chicago from C$ 193

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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
26 Jan — 2 Feb1
1 adult

Cheap flight deals from Ontario to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Ontario (CAON) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 21 January 2025.

Round-trip from

C$ 340

One-way from

C$ 193

Good round-trip deal

C$ 336 or less

Good one-way deal

C$ 219 or less
Porter Airlines
  • Porter Airlines
  • 13/2-17/2
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 6/3
  • 1 total stop
  • 5h 50m total
  • Ontario to Chicago
Search Deals
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 21 January 2025.

Thu 13/28:10 a.m.YYZ - ORD
1 stop5h 49mAir Canada
Sun 16/22:05 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 21/1C$ 338
Thu 13/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 17/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/1C$ 340
Sat 1/36:20 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Wed 5/38:11 a.m.ORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 20/1C$ 343
Wed 16/412:25 p.m.YTZ - ORD
1 stop6h 56mAir Canada
Sun 20/41:55 p.m.ORD - YTZ
1 stop6h 40mAir Canada
Deal found 21/1C$ 345
Thu 13/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Wed 19/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 21/1C$ 347
Sun 9/28:35 a.m.YOW - MDW
1 stop4h 35mPorter Airlines
Thu 13/21:05 p.m.MDW - YOW
1 stop6h 29mPorter Airlines
Deal found 19/1C$ 351
Wed 26/211:20 a.m.YTZ - MDW
1 stop8h 03mMultiple Airlines
Sun 2/311:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 21/1C$ 354
Wed 12/26:40 p.m.YYZ - ORD
Nonstop1h 57mMultiple Airlines
Sat 22/29:50 a.m.ORD - YYZ
Nonstop1h 35mMultiple Airlines
Deal found 20/1C$ 355
Tue 18/22:00 p.m.YTZ - ORD
2 stops21h 40mMultiple Airlines
Tue 25/27:10 a.m.ORD - YTZ
2 stops14h 13mMultiple Airlines
Deal found 21/1C$ 368
Thu 13/26:00 a.m.YYZ - ORD
1 stop4h 16mDelta
Sat 15/24:58 p.m.ORD - YYZ
1 stop4h 51mDelta
Deal found 20/1C$ 383
Fri 21/36:00 a.m.YYZ - MDW
1 stop3h 45mDelta
Tue 25/31:16 p.m.MDW - YYZ
1 stop8h 43mDelta
Deal found 20/1C$ 383
Thu 13/29:00 p.m.YYZ - ORD
Nonstop2h 06mUnited Airlines
Sun 16/28:45 a.m.ORD - YYZ
1 stop4h 33mUnited Airlines
Deal found 21/1C$ 390

Find flights from Ontario to Chicago within your budget

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 21 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 13/2

8:10 a.m.-12:59 p.m.

1 stop5h 49m

Chicago O'Hare Intl

Sun 16/2

2:05 p.m.-4:46 p.m.

Nonstop1h 41m

C$ 338

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Mon 17/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 340

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 1/3

6:20 p.m.-7:20 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 5/3

8:11 a.m.-10:51 a.m.

Nonstop1h 40m

C$ 343

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 16/4

12:25 p.m.-6:21 p.m.

1 stop6h 56m

Chicago O'Hare Intl

Sun 20/4

1:55 p.m.-9:35 p.m.

1 stop6h 40m

C$ 345

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Wed 19/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 347

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 9/2

8:35 a.m.-12:10 p.m.

1 stop4h 35m

Chicago Midway

Thu 13/2

1:05 p.m.-8:34 p.m.

1 stop6h 29m

C$ 351

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 26/2

11:20 a.m.-6:23 p.m.

1 stop8h 03m

Chicago Midway

Sun 2/3

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 354

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/2

6:40 p.m.-7:37 p.m.

Nonstop1h 57m

Chicago O'Hare Intl

Sat 22/2

9:50 a.m.-12:25 p.m.

Nonstop1h 35m

C$ 355

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 18/2

2:00 p.m.-10:40 a.m.

2 stops21h 40m

Chicago O'Hare Intl

Tue 25/2

7:10 a.m.-10:23 p.m.

2 stops14h 13m

C$ 368

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 13/2

6:00 a.m.-9:16 a.m.

1 stop4h 16m

Chicago O'Hare Intl

Sat 15/2

4:58 p.m.-10:49 p.m.

1 stop4h 51m

C$ 383

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

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.

Travel insights for flights from Ontario to Chicago

Get recent, data-driven insights about flights from Ontario to Chicago including ideal travel times, pricing trends, and more.

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$ 355). 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 21 January 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 21 January 2025.

The most flights from CAON to CHI are scheduled on a Monday (52 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 21 January 2025.
Peruse reviews from past customers who have flown with Air Canada, WestJet and United Airlines 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.
Delta
8.0
Very good
8,521 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.3

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.3

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.3

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.3

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
8,521 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.3

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Austrian Airlines
7.6
Good
786 reviews
Delta
8.0
Very good
8,521 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.3

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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$ 193. However, be on the lookout for offers from Air Canada and American Airlines, 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, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Toronto Island - 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 Emirates (92%), Japan Airlines (92%) or Republic Airways (90%) 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$ 1,649 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 219 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 355.

  • 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$ 355). 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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
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Pearson Intl to Midway flights
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Ottawa to Midway flights
Québec City to Midway flights
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Edmonton to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
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St John to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Halifax to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Kelowna to O'Hare Intl flights
Regina to O'Hare Intl flights
Kelowna to Midway flights
Calgary to St. Louis flights
Ottawa to St. Louis flights
Hamilton to O'Hare Intl flights
Victoria to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Bloomington flights
Pearson Intl to Peoria flights
Pearson Intl to Champaign flights
Halifax to St. Louis flights
St. John's to O'Hare Intl flights
Pearson Intl to Moline flights
Saskatoon to St. Louis flights
Saskatoon to O'Hare Intl flights
Vancouver Intl to Peoria flights
Edmonton to St. Louis flights
Québec City to St. Louis flights
Victoria to St. Louis flights
Pearson Intl to Quincy flights
Ottawa to Champaign flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights

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 21 January 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 279AverageC$ 422FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 320AverageC$ 597FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 359AverageC$ 659FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 359AverageC$ 549FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 456AverageC$ 607FlexibilityNo 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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