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Cheap flights from Canada to Chicago (CHI) from $118

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 6/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
YYZ — CHI
May 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
1 adult, Economy
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How far in advance should I book a flight from Canada to Chicago?

Find a great deal and save up to 90% by booking at least 38 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Canada to Chicago within the next two weeks, with the cheapest ticket starting at $344.

What is the cheapest month to fly from Canada to Chicago?

Our data shows that April tends to be the cheapest month to fly to Chicago from Canada. Users have commonly found prices around $292 for the month, but tickets can be as low as $193. Due to multiple factors, prepare for potentially higher prices in September.

When is the cheapest time to fly from Canada to Chicago (CA - CHI)?

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.

Cheap WestJet flights from Canada to Chicago

Explore cheap flight options specifically provided by WestJet for the route between Canada and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Take a peek at the cheapest WestJet flights we've detected traveling from Canada to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Fri 9/612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Fri 9/135:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$199
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$229
Fri 5/318:30 amYVR - ORD
1 stop6h 35mWestJet
Sat 6/15:55 pmORD - YVR
1 stop8h 13mWestJet
Deal found 5/15$255
Fri 5/315:50 amYXX - ORD
1 stop9h 15mWestJet
Sat 6/15:55 pmORD - YXX
1 stop8h 06mWestJet
Deal found 5/15$262
Thu 5/237:00 amYVR - ORD
1 stop8h 05mWestJet
Fri 5/315:55 pmORD - YVR
1 stop8h 13mWestJet
Deal found 5/15$320
Sat 5/255:50 amYXX - ORD
1 stop9h 15mWestJet
Mon 5/275:55 pmORD - YXX
1 stop22h 00mWestJet
Deal found 5/15$350

Cheap Air Canada flights from Canada to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Canada and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Browse through some of the cheapest Air Canada flights traveling from Canada to Chicago. Deals frequently update to provide users with more options.
Sun 7/147:00 amYYZ - ORD
Nonstop1h 56mAir Canada
Wed 7/176:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/14$242
Thu 9/56:15 amYUL - ORD
Nonstop2h 43mAir Canada
Sun 9/87:25 amORD - YUL
1 stop5h 46mAir Canada
Deal found 5/14$256
Thu 9/58:40 amYUL - ORD
1 stop5h 02mAir Canada
Sun 9/87:25 amORD - YUL
1 stop5h 46mAir Canada
Deal found 5/14$261
Sat 6/229:00 amYYZ - ORD
Nonstop1h 54mAir Canada
Mon 6/246:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/16$262
Fri 5/2411:35 pmYVR - ORD
Nonstop4h 01mAir Canada
Mon 5/277:40 pmORD - YVR
Nonstop4h 38mAir Canada
Deal found 5/15$275
Sat 5/258:10 amYVR - ORD
1 stop6h 59mAir Canada
Mon 5/277:40 pmORD - YVR
Nonstop4h 38mAir Canada
Deal found 5/15$280
Sat 5/252:00 pmYYZ - ORD
1 stop7h 16mAir Canada
Tue 5/289:15 pmORD - YYZ
Nonstop1h 43mAir Canada
Deal found 5/14$302
Sat 5/258:30 amYYC - ORD
Nonstop3h 29mAir Canada
Wed 5/297:57 pmORD - YYC
Nonstop3h 46mAir Canada
Deal found 5/14$324
Fri 5/2412:10 amYYC - ORD
1 stop8h 44mAir Canada
Wed 5/297:57 pmORD - YYC
Nonstop3h 46mAir Canada
Deal found 5/14$330

Cheap Canada to Chicago flights in May & June 2024

Find cheap flight options from Canada to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.
Listed are some of the best fares we've found on flights departing from Canada to Chicago in 2024. Check back in a little while for more flight options.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Tue 6/116:30 amYYZ - ORD
1 stop10h 58mMultiple Airlines
Tue 6/186:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/15$216
Tue 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 6/248:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$217
Thu 6/138:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$221
Wed 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/318:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$222
Tue 6/46:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Tue 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/14$224
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$229
Tue 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$233

Canada to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Canada and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Listed are some of the best fares we've found on flights departing from Canada to Chicago in 2024. Check back in a little while for more flight options.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Fri 9/612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Fri 9/135:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$199
Wed 7/1712:30 pmYYC - ORD
Nonstop3h 27mWestJet
Wed 7/245:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$200
Tue 8/2012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Tue 8/275:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$204
Thu 8/2212:30 pmYYC - ORD
Nonstop3h 27mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$212
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Tue 6/116:30 amYYZ - ORD
1 stop10h 58mMultiple Airlines
Tue 6/186:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/15$216
Tue 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 6/248:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$217
Thu 6/138:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$221

Non-stop flights to Chicago from Canada

Discover non-stop flight options from Canada to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Canada to Chicago. Those looking to potentially save on 1 or 2-stop flights from Canada to Chicago should utilize the search form at the the top of the page.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Fri 9/612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Fri 9/135:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$199
Wed 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/318:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$222
Sat 7/1310:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$226
Sun 7/1410:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$229
Tue 8/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 8/228:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$232
Tue 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$233
Wed 6/198:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$235
Tue 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$236

Canada to Chicago flights leaving soon

Find last-minute flight options from Canada to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Have a look at some of the flights available from Canada to Chicago departing last-minute. Users should examine the flight details to ensure there are no surprises.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$229
Sun 5/2612:05 pmYYC - ORD
1 stop16h 15mMultiple Airlines
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mMultiple Airlines
Deal found 5/14$275
Fri 5/2411:35 pmYVR - ORD
Nonstop4h 01mAir Canada
Mon 5/277:40 pmORD - YVR
Nonstop4h 38mAir Canada
Deal found 5/15$275
Sat 5/258:10 amYVR - ORD
1 stop6h 59mAir Canada
Mon 5/277:40 pmORD - YVR
Nonstop4h 38mAir Canada
Deal found 5/15$280
Thu 5/231:45 pmYVR - ORD
Nonstop4h 12mUnited Airlines
Thu 5/3010:35 amORD - YVR
1 stop8h 46mUnited Airlines
Deal found 5/15$281
Wed 5/2211:35 pmYVR - ORD
Nonstop4h 13mUnited Airlines
Sun 5/265:04 amORD - YVR
1 stop6h 47mUnited Airlines
Deal found 5/16$285
Sat 5/2510:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 5/288:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$286

One-way flights to Chicago from Canada

Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Users in need of a one-way flight from Canada to Chicago can choose from these deals. Users can also find round-trip Canada to Chicago flights by using the search form above.
Sat 6/2912:30 pmYYC - ORD
Nonstop3h 27mWestJet
Deal found 5/15$118
Thu 5/308:30 amYYC - ORD
Nonstop3h 29mAir Canada
Deal found 5/14$120
Mon 7/112:30 pmYYC - ORD
Nonstop3h 27mWestJet
Deal found 5/15$123
Wed 5/2912:40 pmYYC - ORD
Nonstop3h 29mUnited Airlines
Deal found 5/15$124
Tue 6/116:30 amYYZ - ORD
1 stop16h 28mMultiple Airlines
Deal found 5/14$126
Thu 6/61:30 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 5/16$126
Mon 6/249:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/15$129
Wed 6/56:30 amYYZ - ORD
1 stop10h 58mMultiple Airlines
Deal found 5/16$131
Tue 5/2112:10 amYYC - ORD
1 stop7h 48mAir Canada
Deal found 5/14$131

Find flights from Canada to Chicago within your budget

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 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$183 - $305

Route

Depart

Return

Price

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Sun 5/26

Nonstop3h 35m

Chicago O'Hare Intl

Mon 8/26

Nonstop3h 45m

$183

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/11

1 stop10h 58m

Chicago O'Hare Intl

Tue 6/18

1 stop18h 20m

$216

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Tue 6/18

Nonstop1h 47m

Chicago Midway

Mon 6/24

Nonstop1h 42m

$217

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 7/14

Nonstop1h 56m

Chicago O'Hare Intl

Wed 7/17

Nonstop1h 48m

$242

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/7

Nonstop1h 55m

Chicago O'Hare Intl

Sun 6/9

Nonstop1h 50m

$243

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Tue 6/4

Nonstop3h 29m

Chicago O'Hare Intl

Fri 6/7

Nonstop3h 46m

$257

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 8/7

2 stops12h 47m

Chicago O'Hare Intl

Tue 8/13

1 stop9h 22m

$261

Vancouver IntlChicago O'Hare Intl

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/30

2 stops10h 01m

Chicago O'Hare Intl

Thu 6/6

1 stop8h 22m

$301

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 6/17

1 stop8h 19m

Chicago Midway

Wed 6/19

1 stop6h 34m

$305

Flights are sorted by cheapest first

Deals found on 5/14

No data available for this route at this time. Please check back soon.

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 May 16, 2024.
Read through reviews of airlines operating flights from Canada to Chicago, such as WestJet, Air Canada and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Food

7.3

Overall

8.1

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Alaska Airlines
8.1
Very good
9,157 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Food

7.3

Overall

8.1

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Delta
8.0
Very good
10,673 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Food

7.3

Overall

8.1

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

KLM
7.9
Good
1,568 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Food

7.3

Overall

8.1

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Aeromexico
7.6
Good
2,528 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Food

7.3

Overall

8.1

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

WestJet
7.5
Good
2,919 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Food

7.3

Overall

8.1

Comfort

7.9

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

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.

  • Can I find flights from Canada to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Canada to Chicago for under $200. The cheapest flight booked recently is on WestJet for just $183, but on average you can expect to pay $227.

  • Are there nonstop flights from Canada to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Canada to Chicago under $200. A good price for a nonstop flight from Canada to Chicago is less than $234.

  • Are there last-minute flights available from Canada to Chicago for under $200?

    There are currently 20+ open flights from Canada to Chicago within the next 7 days for less than $200.

  • What days are nonstop flights available from Canada to Chicago?

    Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Canada to Chicago on average per day?

    29 flight departures from Canada to Chicago per day on average.
    Morning (6am - Noon) - 24% of flight departures
    Afternoon (Noon - 6pm) - 66% of flight departures
    Evening (6pm - Midnight) - 10% of flight departures

  • How long is the flight from Canada to Chicago?

    WestJet, Porter Airlines, and Air Canada can get you from Canada to Chicago in just under 1h 47m. Your travel time will be generally consistent. The distance from Canada to Chicago is about 437 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Canada to Chicago one-way?

    The cheapest airlines for a one-way flight from Canada to Chicago are WestJet ($118), Air Canada ($120), and United Airlines ($124).

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

    The most popular route from Canada to Chicago is Toronto Pearson Intl - Chicago O'Hare Intl. You may also consider Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway.

  • What are the most popular airlines that fly from Canada to Chicago?

    American Airlines, Air Canada and Porter Airlines are the most popular airlines when flying from Canada to Chicago.

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

    The top 3 most reliable airlines when flying from Canada to Chicago are Republic Airways (94%), Copa Airlines (93%) and SkyWest Airlines (92%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $151. On average you can expect to pay $1,627. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $205.

  • What does YYZ to ORD mean?

    This is defined as Toronto Pearson Intl Airport (YYZ) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Canada to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Canada to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Canada to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Canada to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Canada to Chicago that allow pets onboard?

    Many airlines flying from Canada to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Canada to Chicago?

    Yes, you can often find last-minute deals on Canada to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Canada to Chicago flight deals updated?

    The Canada to Chicago flight deals you see on this page were last updated on 5/16.

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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Portland to O'Hare Intl flights

Top 6 airlines flying from Canada to Chicago

Discover the top 6 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 2,637,452 searches. Data last updated May 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$167Average$430FlexibilityNo cancel feeOn-time60%
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American AirlinesCheapest$193Average$440FlexibilityNo cancel feeOn-time71%
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Porter AirlinesCheapest$206Average$341FlexibilityNo cancel feeOn-time52%
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Air CanadaCheapest$209Average$460FlexibilityNo cancel feeOn-time67%
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United AirlinesCheapest$218Average$411FlexibilityNo cancel feeOn-time69%
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DeltaCheapest$334Average$473FlexibilityNo cancel feeOn-timeN/A
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Search flights from Canada to Chicago by cabin class

Find flights from Canada to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Classfrom $597/person
Business Classfrom $406/person
Prem Econ Classfrom $601/person
Economy Classfrom $124/person

Hourly flight availability from Canada to Chicago

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 May 16, 2024.
18%of flight departuresEarly morningMidnight to 6 am
32%of flight departuresMorning6 am to noon
39%of flight departuresAfternoonNoon to 6 pm
11%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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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?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Canada to Chicago, users can toggle the no change fees filter when performing a flight search.

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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