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Cheap flights from Canada to Chicago from C$ 157

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
4 May — 11 May1
1 adult

Cheap flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated 29 April 2025.

Round-trip from

C$ 245

One-way from

C$ 157

Popular in

December

Cheapest in

March

Average price

C$ 351

Good round-trip deal

C$ 258 or less

Good one-way deal

C$ 152 or less
Porter Airlines
  • Porter Airlines
  • 12/7-16/7
  • Nonstop
  • 3h 30m total
  • Canada to Chicago
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Air Canada
  • Air Canada
  • 28/5
  • 1 total stop
  • 7h 55m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 28 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 April 2025
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Price to beat on a round-trip flight from Canada to Chicago (CHI).
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Price to beat on a one-way flight from Canada to Chicago (CHI).
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Find flight deals from Canada to Chicago

Cheapest flights from Canada to Chicago
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 April 2025.

Sat 12/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 16/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 28/4C$ 245
Thu 28/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Mon 1/99:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 28/4C$ 249
Fri 6/611:00 a.m.YYZ - ORD
Nonstop2h 01mAir Canada
Sun 8/67:04 a.m.ORD - YYZ
Nonstop1h 54mAir Canada
Deal found 28/4C$ 252
Fri 6/67:25 a.m.YTZ - ORD
1 stop4h 59mAir Canada
Sun 8/62:07 p.m.ORD - YTZ
1 stop6h 28mAir Canada
Deal found 28/4C$ 256
Fri 23/58:30 a.m.YYC - ORD
Nonstop3h 33mUnited Airlines
Tue 27/57:10 a.m.ORD - YYC
1 stop15h 38mUnited Airlines
Deal found 28/4C$ 258
Tue 10/612:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Tue 24/65:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 28/4C$ 265
Fri 23/58:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Tue 27/54:43 p.m.ORD - YYC
1 stop9h 20mAir Canada
Deal found 28/4C$ 266
Mon 15/97:20 a.m.YYZ - ORD
1 stop8h 53mMultiple Airlines
Mon 22/93:50 p.m.ORD - YYZ
Nonstop1h 43mMultiple Airlines
Deal found 28/4C$ 297
Wed 13/86:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Mon 18/88:34 p.m.ORD - YYC
Nonstop3h 55mAmerican Airlines
Deal found 28/4C$ 302
Mon 12/51:30 p.m.YYC - ORD
1 stop6h 47mMultiple Airlines
Tue 13/52:22 p.m.ORD - YYC
1 stop9h 16mMultiple Airlines
Deal found 28/4C$ 308
Wed 28/52:00 p.m.YYC - ORD
1 stop6h 40mDelta
Mon 2/611:03 a.m.ORD - YYC
2 stops12h 58mDelta
Deal found 28/4C$ 309
Thu 10/73:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Sun 13/75:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 28/4C$ 310

Cheapflights Fare Finder

Customize your flight search to find flights from Canada 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 29 April 2025.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 12/7

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

Nonstop1h 50m

Chicago Midway

Wed 16/7

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

Nonstop1h 40m

C$ 245

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 28/8

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

Nonstop1h 50m

Chicago Midway

Mon 1/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/6

11:00 a.m.-12:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Sun 8/6

7:04 a.m.-9:58 a.m.

Nonstop1h 54m

C$ 252

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 6/6

7:25 a.m.-11:24 a.m.

1 stop4h 59m

Chicago O'Hare Intl

Sun 8/6

2:07 p.m.-9:35 p.m.

1 stop6h 28m

C$ 256

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 23/5

8:30 a.m.-1:03 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Tue 27/5

7:10 a.m.-9:48 p.m.

1 stop15h 38m

C$ 258

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/6

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

Chicago O'Hare Intl

Tue 24/6

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 265

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 23/5

8:10 a.m.-4:51 p.m.

1 stop7h 41m

Chicago O'Hare Intl

Tue 27/5

4:43 p.m.-1:03 a.m.

1 stop9h 20m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 15/9

7:20 a.m.-3:13 p.m.

1 stop8h 53m

Chicago O'Hare Intl

Mon 22/9

3:50 p.m.-6:33 p.m.

Nonstop1h 43m

C$ 297

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 13/8

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Mon 18/8

8:34 p.m.-11:29 p.m.

Nonstop3h 55m

C$ 302

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 12/5

1:30 p.m.-9:17 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Tue 13/5

2:22 p.m.-10:38 p.m.

1 stop9h 16m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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

Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada 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 Canada to Chicago

What is the cheapest month to book a flight from Canada to Chicago?

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 261). Flying from Canada 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 CA to CHI?

Find hourly flight availability from Canada 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 29 April 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.

Weekly flight availability from Canada to Chicago

Explore weekly flight availability from Canada 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 29 April 2025.

The most flights from CA0 to CHI are scheduled on a Tuesday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 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 29 April 2025.
See what other customers who have flown with Alaska Airlines, Porter Airlines and Delta from Canada to Chicago have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,949 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Porter Airlines
8.0
Very good
285 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Air Transat
7.8
Good
385 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,697 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Canada 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 Canada to Chicago one-way?

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at C$ 157. American Airlines flights start at C$ 161 while deals on United Airlines start at C$ 162 one-way.

  • What are the most popular routes from Canada to Chicago?

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

  • What are the most reliable airlines from Canada to Chicago?

    Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: Copa Airlines (90%), Egyptair (89%), ANA( 85%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 183. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 224 on average our data indicates C$ 1,266 when flying from Canada to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Canada 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 Canada to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 261). Flying from Canada 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 Canada to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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St. John's to O'Hare Intl flights
St John to O'Hare Intl flights
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Regina to O'Hare Intl flights
Deer Lake to O'Hare Intl flights
Comox to O'Hare Intl flights

Top 7 airlines flying from Canada to Chicago

Discover the top 7 airlines that operate flights from Canada 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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapestC$ 147AverageC$ 452FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 154AverageC$ 501FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 170AverageC$ 451FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 178AverageC$ 497FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 243AverageC$ 551FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 260AverageC$ 441FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Alaska AirlinesCheapestC$ 360AverageC$ 501FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines 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 Canada to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Canada to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.

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

Certainly. Search results for flights to Chicago from Canada 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 Canada to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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