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Mississauga

$75+ Cheap flights from Chicago (CHI) to Mississauga, Canada

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Mississauga are usually found in June or July, booked 68 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Chicago to Mississauga

Keep the following information in mind while searching for Chicago to Mississauga flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$199
(Kiwi.com)

One-way from

$75
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$341
From Chicago (CHI) to Mississauga
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One-way flight from Chicago (CHI) to Mississauga
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Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Mississauga

Cheapest flights from Chicago to Mississauga
Explore the most affordable flight options available from Chicago to Mississauga. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/237:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
lun. 10/274:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/15$199
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/227:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
dom. 10/264:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 9/15$207
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/75:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
lun. 10/134:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/13$212
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/317:51 pmORD - YYZ
1 stop17h 29mMultiple Airlines
vie. 11/712:50 pmYYZ - ORD
1 stop9h 33mMultiple Airlines
Deal found 9/16$214
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
lun. 11/34:00 pmYYZ - ORD
1 stop7h 39mMultiple Airlines
Deal found 9/15$216
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
dom. 11/94:00 pmYYZ - ORD
1 stop19h 42mMultiple Airlines
Deal found 9/15$217
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/67:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
lun. 10/134:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/13$218
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/16:00 amORD - YYZ
1 stop7h 20mMultiple Airlines
lun. 11/34:00 pmYYZ - ORD
1 stop7h 39mMultiple Airlines
Deal found 9/15$220
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
dom. 11/24:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 9/15$223
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/2312:53 pmORD - YYZ
1 stop7h 14mMultiple Airlines
dom. 10/264:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 9/14$224
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/255:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
lun. 10/274:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/14$226
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/319:32 amMDW - YYZ
1 stop9h 28mMultiple Airlines
vie. 11/712:50 pmYYZ - MDW
1 stop10h 30mMultiple Airlines
Deal found 9/16$241

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Mississauga 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 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from Chicago to Mississauga that are best for you.

Fly from

Chicago

Fly to

Mississauga

Route

Depart

Return

Price

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

jue. 10/23

9:20 am-12:31 am

2 stops14h 11m

Toronto Pearson Intl

jue. 10/30

5:15 pm-8:32 am

1 stop16h 17m

$287

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

sáb. 11/22

9:41 am-4:02 pm

1 stop5h 21m

Toronto Pearson Intl

sáb. 11/22

6:10 pm-9:52 am

1 stop16h 42m

$295

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

jue. 2/19

7:00 am-11:34 am

1 stop3h 34m

Toronto Pearson Intl

mar. 2/24

10:20 am-4:17 pm

1 stop6h 57m

$302

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

lun. 10/6

9:20 am-11:18 pm

1 stop12h 58m

Toronto Pearson Intl

mar. 10/14

6:00 pm-9:40 am

1 stop16h 40m

$302

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

vie. 10/24

9:00 am-9:21 pm

2 stops11h 21m

Toronto Pearson Intl

lun. 10/27

6:00 pm-9:40 am

1 stop16h 40m

$312

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

vie. 11/28

9:41 am-4:02 pm

1 stop5h 21m

Toronto Pearson Intl

mar. 12/2

6:10 pm-9:54 am

1 stop16h 44m

$325

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

mié. 10/15

12:48 pm-11:58 pm

1 stop10h 10m

Toronto Pearson Intl

sáb. 10/18

6:20 am-10:30 am

1 stop5h 10m

$327

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

vie. 10/10

6:59 pm-8:55 am

1 stop12h 56m

Toronto Pearson Intl

vie. 10/17

3:35 pm-8:23 pm

1 stop5h 48m

$330

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

dom. 10/5

7:10 am-8:55 am

1 stop24h 45m

Toronto Pearson Intl

vie. 10/17

3:35 pm-8:23 pm

1 stop5h 48m

$330

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

mié. 11/19

8:55 am-2:48 pm

1 stop4h 53m

Toronto Pearson Intl

jue. 11/20

9:52 am-4:28 pm

1 stop7h 36m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 46 results
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Best time to book a flight from Chicago to Mississauga

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

How far ahead should I book a flight from Chicago to Mississauga?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Mississauga. Price data was last updated on September 12, 2025.

The price you pay for your flight from Chicago to Mississauga may vary depending on when you book. For the best chance of a lower fare, look to book 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Mississauga (average of $243). Flying from Chicago to Mississauga in August is currently the most expensive (average of $348). 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 CHI to M1S?

Find hourly flight availability from Chicago to Mississauga. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

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

What is the cheapest day to fly from Chicago to Mississauga?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Mississauga. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago to Mississauga flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Mississauga

Explore weekly flight availability from Chicago to Mississauga. 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 septiembre 16, 2025.

The most flights from CHI to M1S are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).

Reviews of airlines servicing Mississauga

Get insights into the airlines that provide service to Mississauga. 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 Mississauga. Reviews last updated septiembre 16, 2025.
Get a feel of what it's like to fly with Porter Airlines, United Airlines, and American Airlines from Chicago to Mississauga by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,924 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Mississauga. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Mississauga?

    A quick flight from Chicago to Mississauga can take about 5h 21m. WestJet provides one of the quickest options available for as low as $295. Chicago and Mississauga are separated by a distance of 432 mi.

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

    The top 3 most reliable airlines when flying from Chicago to Mississauga are Qatar Airways (88%), Envoy Air (86%) and SkyWest Airlines (81%).

  • What are the cheapest flights from Chicago to Mississauga?

    Looking at all options, your cheapest flight can be booked for $74. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $199 on average, our data indicates $762 when flying from Chicago to Mississauga.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Mississauga (average of $243). Flying from Chicago to Mississauga in August is currently the most expensive (average of $348). 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.

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Alternative routes for Chicago to Mississauga

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Mississauga

Discover the top 4 airlines that operate flights from Chicago to Mississauga. 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 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$118Average$270FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$146Average$307FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$187Average$257FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$226Average$391FlexibilityNo cancel feeOn-time71%

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