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Mississauga

$87+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Jan 9 — Jan 161
Fri 1/9
Fri 1/16
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Mississauga are usually found in June or November, booked 68 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap 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 December 10, 2025.

This United Airlines deal was found by Cheapflights users on 12/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amORD - YYZ
1 stop13h 56mUnited Airlines
Mon 1/59:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/8$252
This United Airlines deal was found by Cheapflights users on 12/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amORD - YYZ
1 stop13h 56mUnited Airlines
Wed 12/319:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/9$253
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Mon 12/293:30 pmYYZ - ORD
Nonstop2h 10mUnited Airlines
Deal found 12/10$274
This United Airlines deal was found by Cheapflights users on 12/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Sun 1/186:50 amYYZ - ORD
Nonstop2h 15mUnited Airlines
Deal found 12/7$275
This United Airlines deal was found by Cheapflights users on 12/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:16 pmORD - YYZ
Nonstop2h 05mUnited Airlines
Sun 1/189:00 amYYZ - ORD
Nonstop2h 06mUnited Airlines
Deal found 12/7$285
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Mon 12/156:15 amMDW - YYZ
2 stops31h 05mMultiple Airlines
Thu 12/187:10 amYYZ - MDW
1 stop15h 48mMultiple Airlines
Deal found 12/8$301
This United Airlines deal was found by Cheapflights users on 12/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:20 pmORD - YYZ
Nonstop1h 39mUnited Airlines
Thu 1/19:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/8$324
This United Airlines deal was found by Cheapflights users on 12/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Thu 1/19:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/8$334
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Sun 12/147:27 pmMDW - YYZ
2 stops41h 53mMultiple Airlines
Thu 12/187:10 amYYZ - MDW
1 stop15h 48mMultiple Airlines
Deal found 12/8$367
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Fri 12/123:52 pmMDW - YYZ
1 stop21h 28mMultiple Airlines
Mon 12/157:10 amYYZ - MDW
2 stops26h 36mMultiple Airlines
Deal found 12/7$384
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Wed 12/246:12 amMDW - YYZ
2 stops15h 00mMultiple Airlines
Wed 12/317:15 amYYZ - MDW
1 stop15h 43mMultiple Airlines
Deal found 12/9$408
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Mon 12/156:15 amMDW - YYZ
2 stops31h 05mMultiple Airlines
Wed 12/176:12 pmYYZ - MDW
1 stop16h 42mMultiple Airlines
Deal found 12/8$411

Find flight deals from Chicago to Mississauga

Keep the following information in mind while searching for Chicago to Mississauga flight deals. Data was last updated December 10, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$185
(Gotogate)

One-way from

$87
(Gotogate)

Popular in

February

Cheapest in

June

Average price

$321
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Chicago (CHI) to Mississauga
Search Deals
One-way flight from Chicago (CHI) to Mississauga
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 10, 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

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 1/30

9:15 pm-11:59 pm

Nonstop1h 44m

Toronto Pearson Intl

Mon 2/2

9:00 am-10:06 am

Nonstop2h 06m

$210

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 1/31

11:15 am-2:01 pm

Nonstop1h 46m

Toronto Pearson Intl

Mon 2/2

5:30 pm-6:50 pm

Nonstop2h 20m

$211

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 1/31

1:00 pm-6:57 pm

1 stop4h 57m

Toronto Pearson Intl

Tue 2/3

9:00 pm-10:05 pm

Nonstop2h 05m

$220

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 1/29

7:10 am-1:43 pm

1 stop5h 33m

Toronto Pearson Intl

Mon 2/2

3:30 pm-4:40 pm

Nonstop2h 10m

$220

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 2/19

7:10 am-1:24 pm

1 stop5h 14m

Toronto Pearson Intl

Sun 2/22

6:15 am-9:41 am

1 stop4h 26m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/10

6:35 pm-10:42 pm

1 stop3h 07m

Toronto Pearson Intl

Fri 2/13

10:05 am-5:37 pm

1 stop8h 32m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 2/18

1:28 pm-10:40 pm

1 stop8h 12m

Toronto Pearson Intl

Wed 2/25

6:15 am-12:46 pm

1 stop7h 31m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 2/15

1:28 pm-7:09 pm

1 stop4h 41m

Toronto Pearson Intl

Tue 2/24

6:15 am-8:53 am

1 stop3h 38m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/17

1:28 pm-7:09 pm

1 stop4h 41m

Toronto Pearson Intl

Mon 2/23

12:11 pm-5:37 pm

1 stop6h 26m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 2/18

1:28 pm-10:40 pm

1 stop8h 12m

Toronto Pearson Intl

Sun 2/22

6:15 am-8:53 am

1 stop3h 38m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 40 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 December 5, 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, March is the cheapest month in which you can book a flight from Chicago to Mississauga (average of $79). Flying from Chicago to Mississauga in December is currently the most expensive (average of $210). 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 December 10, 2025.

It’s optimal to fly from Chicago to Mississauga in the morning. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight at noon.

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 December 6, 2025.

Travelers seeking maximum savings on their Chicago to Mississauga flight should consider departing on Monday mornings when fares are most often at their lowest. Monday evenings 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 December 10, 2025.

The most flights from CHI to M1S are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 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 December 10, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and Air Canada 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.
United Airlines
7.4
Good
9,092 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,047 reviews
United Airlines
7.4
Good
9,092 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Air Canada
7.1
Good
10,513 reviews
United Airlines
7.4
Good
9,092 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 1h 44m. United Airlines provides one of the quickest options available for as low as $210. Chicago and Mississauga are separated by a distance of 436 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $64 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $69 and $74, respectively.

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

    The top 3 most reliable airlines when flying from Chicago to Mississauga are Korean Air (94%), SkyWest Airlines (82%) and Japan Airlines (79%).

  • What are the cheapest flights from Chicago to Mississauga?

    Looking at all options, your cheapest flight can be booked for $94. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $166 on average, our data indicates $922 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, March is the cheapest month in which you can book a flight from Chicago to Mississauga (average of $79). Flying from Chicago to Mississauga in December is currently the most expensive (average of $210). 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 Chicago to Mississauga

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pierre Elliott Trudeau Intl flights
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Midway to Thunder Bay flights
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Bloomington to Pierre Elliott Trudeau Intl flights
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Dubuque to Pearson Intl flights
Bloomington to Ottawa flights
O'Hare Intl to Kingston flights

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 December 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$116Average$246FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$146Average$300FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$185Average$350FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$215Average$378FlexibilityNo cancel feeOn-time71%

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