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Cheap flights from Canada to Chicago (CHI) from $114

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 6/1. 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 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
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 $337.

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 August.

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 2,749,864 searches. Data last updated May 8, 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.
Wed 7/1012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/145:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/6$189
Wed 7/1012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/145:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/7$190
Fri 7/2612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/285:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/6$220
Wed 7/106:30 amYVR - ORD
1 stop8h 27mWestJet
Mon 7/155:55 pmORD - YVR
1 stop7h 09mWestJet
Deal found 5/6$277
Fri 5/177:10 amYUL - ORD
1 stop14h 45mWestJet
Wed 5/227:09 amORD - YUL
1 stop9h 35mWestJet
Deal found 5/7$413
Tue 5/146:04 pmYYZ - ORD
1 stop6h 51mWestJet
Wed 5/156:07 amORD - YYZ
1 stop4h 32mWestJet
Deal found 5/7$414
Sat 5/186:34 amYYZ - ORD
1 stop16h 03mWestJet
Tue 5/219:36 amORD - YYZ
1 stop12h 38mWestJet
Deal found 5/7$427

Cheap Delta flights from Canada to Chicago

Explore cheap flight options specifically provided by Delta 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 2,749,864 searches. Data last updated May 8, 2024.
Browse through some of the cheapest Delta flights traveling from Canada to Chicago. Deals frequently update to provide users with more options.
Sat 10/266:50 amYYC - ORD
1 stop8h 55mDelta
Tue 10/296:00 amORD - YYC
1 stop8h 52mDelta
Deal found 5/7$228
Mon 6/176:45 amYYC - ORD
2 stops13h 53mDelta
Tue 7/231:45 pmORD - YYC
1 stop10h 18mDelta
Deal found 5/6$239
Sat 6/86:45 amYYC - ORD
2 stops12h 02mDelta
Tue 6/111:40 pmORD - YYC
1 stop10h 22mDelta
Deal found 5/6$249
Fri 10/2512:25 pmYYC - ORD
1 stop8h 22mDelta
Tue 10/296:00 amORD - YYC
1 stop8h 52mDelta
Deal found 5/7$254
Thu 9/2612:30 pmYYC - ORD
Nonstop3h 39mDelta
Wed 10/211:19 amORD - YYC
1 stop9h 44mDelta
Deal found 5/7$261
Wed 5/1512:30 pmYYZ - MDW
1 stop5h 36mDelta
Wed 5/292:15 pmMDW - YYZ
1 stop7h 59mDelta
Deal found 5/7$333
Wed 5/156:04 amYYZ - ORD
1 stop5h 13mDelta
Sat 5/183:50 pmORD - YYZ
1 stop6h 24mDelta
Deal found 5/8$383
Mon 5/135:59 pmYYZ - ORD
1 stop3h 56mDelta
Thu 5/161:32 pmORD - YYZ
1 stop8h 14mDelta
Deal found 5/6$395

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 2,749,864 searches. Prices were last updated on May 8, 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.
Wed 5/156:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/299:15 pmORD - YYZ
2 stops21h 20mMultiple Airlines
Deal found 5/7$212
Tue 6/46:30 amYYZ - ORD
1 stop11h 05mMultiple Airlines
Tue 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/7$215
Wed 6/56:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 6/126:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/7$217
Sat 6/110:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/148:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$217
Tue 6/47:45 amYYZ - ORD
2 stops25h 36mMultiple Airlines
Tue 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/7$218
Tue 6/43:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/812:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$218
Sat 6/110:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 6/38:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$219
Wed 5/156:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/295:41 pmORD - YYZ
3 stops24h 54mMultiple Airlines
Deal found 5/7$220
Tue 6/43:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/118:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$220

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 2,749,864 searches. Data last updated May 8, 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.
Wed 7/1012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/145:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/7$190
Wed 5/156:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/299:15 pmORD - YYZ
2 stops21h 20mMultiple Airlines
Deal found 5/7$212
Tue 6/46:30 amYYZ - ORD
1 stop11h 05mMultiple Airlines
Tue 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/7$215
Wed 6/56:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 6/126:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/7$217
Sat 6/110:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/148:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$217
Tue 6/47:45 amYYZ - ORD
2 stops25h 36mMultiple Airlines
Tue 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/7$218
Tue 6/43:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/812:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$218
Sat 6/110:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 6/38:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$219
Wed 5/156:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/295:41 pmORD - YYZ
3 stops24h 54mMultiple Airlines
Deal found 5/7$220

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 2,749,864 searches. Data last updated May 8, 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.
Wed 7/1012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/145:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/7$190
Sat 7/2010:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 7/278:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$214
Wed 5/223:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 5/258:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$217
Tue 5/219:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 5/2512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$218
Tue 6/49:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 6/611:25 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$219
Mon 6/38:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 6/108:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$220
Tue 6/43:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/1111:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$221
Wed 7/1012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/145:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/7$222
Sat 6/110:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 6/511:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/6$225

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 2,749,864 searches. Data last updated May 8, 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.
Wed 5/156:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/299:15 pmORD - YYZ
2 stops21h 20mMultiple Airlines
Deal found 5/7$212
Wed 5/156:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/295:41 pmORD - YYZ
3 stops24h 54mMultiple Airlines
Deal found 5/7$220
Tue 5/146:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/1511:14 amORD - YYZ
3 stops31h 21mMultiple Airlines
Deal found 5/7$233
Tue 5/146:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Wed 5/158:09 pmORD - YYZ
2 stops22h 26mMultiple Airlines
Deal found 5/7$242
Tue 5/142:40 pmYYZ - ORD
2 stops20h 15mMultiple Airlines
Wed 5/155:41 pmORD - YYZ
3 stops24h 54mMultiple Airlines
Deal found 5/7$259
Wed 5/156:30 amYYZ - ORD
1 stop11h 05mMultiple Airlines
Wed 5/2910:58 amORD - YYZ
1 stop9h 17mMultiple Airlines
Deal found 5/7$267
Sat 5/186:15 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 5/228:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$271
Thu 5/1612:30 pmYYC - ORD
Nonstop3h 35mMultiple Airlines
Mon 5/209:25 pmORD - YYC
1 stop14h 56mMultiple Airlines
Deal found 5/7$273
Wed 5/159:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 5/295:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/7$280

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 2,749,864 searches. Data last updated May 8, 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 6/112:30 pmYYC - ORD
Nonstop3h 35mWestJet
Deal found 5/7$114
Tue 5/146:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Deal found 5/7$116
Tue 5/146:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
Deal found 5/7$117
Wed 8/2812:30 pmYYC - ORD
Nonstop3h 27mWestJet
Deal found 5/7$118
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Deal found 5/6$120
Tue 6/48:30 amYYC - ORD
Nonstop3h 29mAir Canada
Deal found 5/6$122
Wed 5/156:30 amYYZ - ORD
1 stop11h 05mMultiple Airlines
Deal found 5/7$125
Tue 6/47:45 amYYZ - ORD
1 stop15h 01mMultiple Airlines
Deal found 5/7$126
Tue 6/46:30 amYYZ - ORD
1 stop17h 59mMultiple Airlines
Deal found 5/7$127

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 2,749,864 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$189 - $310

Route

Depart

Return

Price

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 7/10

Nonstop3h 27m

Chicago O'Hare Intl

Sun 7/14

Nonstop3h 45m

$189

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/4

1 stop11h 05m

Chicago O'Hare Intl

Tue 6/11

1 stop18h 20m

$215

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Sat 6/1

Nonstop1h 47m

Chicago Midway

Fri 6/14

Nonstop1h 42m

$217

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Sat 10/26

1 stop8h 55m

Chicago O'Hare Intl

Tue 10/29

1 stop8h 52m

$228

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 6/5

Nonstop2h 02m

Chicago O'Hare Intl

Wed 6/12

Nonstop1h 45m

$242

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/30

Nonstop2h 02m

Chicago O'Hare Intl

Sun 6/2

Nonstop1h 52m

$243

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 5/31

Nonstop1h 56m

Chicago O'Hare Intl

Mon 6/3

Nonstop1h 35m

$251

Vancouver IntlChicago O'Hare Intl

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/10

2 stops10h 31m

Chicago O'Hare Intl

Sat 10/12

2 stops11h 00m

$307

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/23

Nonstop2h 02m

Chicago O'Hare Intl

Sun 5/26

Nonstop1h 45m

$310

Flights are sorted by cheapest first

Deals found on 5/6

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 8, 2024.
Read through reviews of airlines operating flights from Canada to Chicago, such as WestJet, Delta and Air Canada. 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
9,147 reviews
Check prices

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.6

Entertainment

7.3

Overall

8.1

Reviews

1 / 10

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

Alaska Airlines
8.1
Very good
9,147 reviews
Alaska Airlines
8.1
Very good
9,147 reviews
Check prices

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.6

Entertainment

7.3

Overall

8.1

Reviews

1 / 10

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

Delta
8.1
Very good
10,810 reviews
Alaska Airlines
8.1
Very good
9,147 reviews
Check prices

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.6

Entertainment

7.3

Overall

8.1

Reviews

1 / 10

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

Aeromexico
7.6
Good
2,565 reviews
Alaska Airlines
8.1
Very good
9,147 reviews
Check prices

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.6

Entertainment

7.3

Overall

8.1

Reviews

1 / 10

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

WestJet
7.6
Good
2,945 reviews
Alaska Airlines
8.1
Very good
9,147 reviews
Check prices

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.6

Entertainment

7.3

Overall

8.1

Reviews

1 / 10

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

Porter Airlines
7.4
Good
423 reviews
Alaska Airlines
8.1
Very good
9,147 reviews
Check prices

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.6

Entertainment

7.3

Overall

8.1

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 $189, but on average you can expect to pay $218.

  • 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 $225.

  • Are there last-minute flights available from Canada to Chicago for under $300?

    There are currently 20+ open flights from Canada to Chicago within the next 7 days for less than $300.

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

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

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

    13 flight departures from Canada to Chicago per day on average.
    Morning (6am - Noon) - 38% of flight departures
    Afternoon (Noon - 6pm) - 62% of flight departures

  • How long is the flight from Canada to Chicago?

    WestJet, Porter Airlines, and Delta can get you from Canada to Chicago in just under 1h 47m. Your travel time can differ by up to 7h 08m. The distance from Canada to Chicago is about 437 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 ($114), Air Canada ($122), and Porter Airlines ($129).

  • 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 (98%), SkyWest Airlines (94%) and Copa Airlines (94%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $150. On average you can expect to pay $1,541. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $242.

  • 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 5/7.

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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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 2,749,864 searches. Data last updated May 8, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$193Average$435FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapest$206Average$341FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapest$211Average$430FlexibilityNo cancel feeOn-time60%
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Air CanadaCheapest$211Average$461FlexibilityNo cancel feeOn-time67%
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United AirlinesCheapest$218Average$413FlexibilityNo 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 $596/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 8, 2024.
16%of flight departuresEarly morningMidnight to 6 am
34%of flight departuresMorning6 am to noon
41%of flight departuresAfternoonNoon to 6 pm
9%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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