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Cheap flights from Ontario to Chicago from C$ 185

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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
26 Feb — 5 Mar1
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 21 February 2025.

Round-trip from

C$ 294

One-way from

C$ 186

Popular in

December

Cheapest in

April

Average price

C$ 405

Good round-trip deal

C$ 282 or less

Good one-way deal

C$ 175 or less
Porter Airlines
  • Porter Airlines
  • 19/3-22/3
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
Search Deals
17/3
  • 17/3
  • 1 total stop
  • 24h 13m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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).
Search Deals

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 February 2025.

Sat 24/54:00 p.m.YYZ - ORD
1 stop5h 12mAir Canada
Sat 7/610:40 a.m.ORD - YYZ
1 stop6h 18mAir Canada
Deal found 20/2C$ 290
Thu 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/35:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/2C$ 290
Sat 24/510:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Sat 7/610:40 a.m.ORD - YTZ
1 stop6h 10mAir Canada
Deal found 20/2C$ 290
Thu 13/39:00 p.m.YYZ - ORD
Nonstop2h 06mMultiple Airlines
Thu 10/47:10 a.m.ORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 19/2C$ 315
Thu 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Thu 27/35:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 18/2C$ 317
Fri 18/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 19/412:55 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 20/2C$ 347
Sat 12/46:30 a.m.YYZ - MDW
1 stop13h 03mWestJet
Mon 21/41:16 p.m.MDW - YYZ
1 stop21h 18mWestJet
Deal found 20/2C$ 347
Sat 26/412:45 p.m.YYZ - ORD
1 stop4h 59mUnited Airlines
Wed 30/411:15 a.m.ORD - YYZ
1 stop4h 54mUnited Airlines
Deal found 20/2C$ 349
Thu 20/310:20 a.m.YYZ - MDW
1 stop3h 16mDelta
Mon 24/32:55 p.m.MDW - YYZ
1 stop6h 43mDelta
Deal found 19/2C$ 351
Fri 18/49:45 a.m.YYZ - ORD
1 stop7h 23mDelta
Sat 19/45:00 p.m.ORD - YYZ
1 stop4h 55mDelta
Deal found 20/2C$ 359
Sat 15/33:30 p.m.YUL - ORD
1 stop9h 26mMultiple Airlines
Wed 19/35:55 a.m.ORD - YUL
3 stops33h 50mMultiple Airlines
Deal found 19/2C$ 368
Sun 6/46:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Sun 13/411:15 a.m.MDW - YUL
1 stop4h 37mPorter Airlines
Deal found 20/2C$ 368

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 February 2025.

Fly from

Ontario

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 24/5

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Sat 7/6

10:40 a.m.-5:58 p.m.

1 stop6h 18m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/3

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

Mon 24/3

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 24/5

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

1 stop5h 30m

Chicago O'Hare Intl

Sat 7/6

10:40 a.m.-5:50 p.m.

1 stop6h 10m

C$ 290

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 13/3

9:00 p.m.-10:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Thu 10/4

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 315

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/3

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Thu 20/3

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 325

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/4

6:30 a.m.-6:33 p.m.

1 stop13h 03m

Chicago Midway

Sun 20/4

10:20 a.m.-11:34 a.m.

1 stop24h 14m

C$ 347

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 18/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Sat 19/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

C$ 347

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 26/4

12:45 p.m.-4:44 p.m.

1 stop4h 59m

Chicago O'Hare Intl

Wed 30/4

11:15 a.m.-5:09 p.m.

1 stop4h 54m

C$ 349

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

Chicago Midway

Mon 24/3

2:55 p.m.-10:38 p.m.

1 stop6h 43m

C$ 351

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

9:45 a.m.-4:08 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Sat 19/4

5:00 p.m.-10:55 p.m.

1 stop4h 55m

C$ 359

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

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 February 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 February 2025.

The most flights from CAON to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 February 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines 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.
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

Air Transat
7.8
Good
380 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

Austrian Airlines
7.6
Good
773 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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$ 186. However, be on the lookout for offers from Air Canada and United 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, Toronto Pearson Intl - 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 Emirates (90%), Republic Airways (89%) or ANA (84%) 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$ 1,415 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 189 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 304.

  • 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.
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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 21 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 267AverageC$ 416FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 315AverageC$ 584FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 350AverageC$ 634FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 354AverageC$ 541FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 450AverageC$ 611FlexibilityNo 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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