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Cheap flights from Canada to Chicago from C$ 125

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
13 Dec — 20 Dec1
1 adult
1 adult, Economy, 0 bags

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 13 November 2025.

Round-trip from

C$ 240

One-way from

C$ 125

Popular in

December

Cheapest in

July

Average price

C$ 398

Good round-trip deal

C$ 346 or less

Good one-way deal

C$ 197 or less
WestJet
  • WestJet
  • 2/2-27/2
  • Nonstop
  • 7h 30m total
  • Canada to Chicago
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WestJet
  • WestJet
  • 9/5
  • Nonstop
  • 3h 28m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Canada to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Canada to Chicago (CHI).
Search Deals

Find flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

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 13 November 2025.

Fri 5/129:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Fri 12/122:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Deal found 12/11C$ 241
Thu 18/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 261
Fri 19/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 265
Wed 26/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/126:05 a.m.ORD - YYZ
1 stop4h 51mAmerican Airlines
Deal found 12/11C$ 266
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 15/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/11C$ 268
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/125:00 a.m.ORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 12/11C$ 270
Fri 28/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 30/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 272
Thu 27/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 29/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 273
Sat 6/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Sun 7/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 11/11C$ 275
Fri 5/125:35 a.m.YYC - ORD
1 stop8h 35mMultiple Airlines
Fri 12/122:20 p.m.ORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 12/11C$ 275
Thu 27/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 30/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 275
Tue 9/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Tue 16/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 10/11C$ 277

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 13 November 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

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 2/3

9:00 p.m.-10:04 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Thu 5/3

6:40 p.m.-9:28 p.m.

Nonstop1h 48m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/5

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

Nonstop1h 50m

Chicago Midway

Mon 4/5

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 14/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sat 29/11

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 30/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 18/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 6/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 2/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 4/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 279

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 30/11

1:19 p.m.-4:02 p.m.

Nonstop1h 43m

C$ 283

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/5

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 4/5

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 19/4

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 116). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 199). 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 13 November 2025.

It’s typically best to fly out from Canada to Chicago in the evening. Doing so could potentially save you 24% on the flight price compared to flying at noon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Friday afternoons 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 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 13 November 2025.

The most flights from CA0 to CHI are scheduled on a Thursday (60 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 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 13 November 2025.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andAmerican Airlines from Canada to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
United Airlines
7.4
Good
9,015 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
American Airlines
7.2
Good
11,050 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
WestJet
7.2
Good
3,159 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Air Canada
7.1
Good
10,444 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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.

  • How long is the flight from Canada to Chicago?

    A quick flight from Canada to Chicago can take about 1h 50m. United Airlines provides one of the quickest options available for as low as C$ 272. Canada and Chicago are separated by a distance of 711 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 139. United Airlines flights start at C$ 160 while deals on Delta start at C$ 179 one-way.

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

    When deciding which route to take from Canada to Chicago consider Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl, Toronto Pearson Intl - Chicago O'Hare Intl or Vancouver 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: EVA Air (94%), Egyptair (92%), ANA( 88%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 220. While the most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) can be booked for C$ 247 on average, our data indicates C$ 2,090 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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 116). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 199). 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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Pearson Intl to St. Louis flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Halifax to O'Hare Intl flights
Halifax to Midway flights
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Edmonton to Midway flights
Ottawa to Midway flights
Saskatoon to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Québec City to Midway flights
Mexico City to O'Hare Intl flights
Saskatoon to Midway flights
Edmonton to St. Louis flights
Vancouver Intl to St. Louis flights
Kelowna to O'Hare Intl flights
Kelowna to Midway flights
Seattle to O'Hare Intl flights
Ottawa to St. Louis flights
Québec City to St. Louis flights
Pearson Intl to Peoria flights
Victoria to O'Hare Intl flights
Regina to O'Hare Intl flights
Pearson Intl to Moline flights
Halifax to St. Louis flights
St. John's to O'Hare Intl flights
Victoria to Midway flights
Nanaimo to O'Hare Intl flights
Detroit to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Fort McMurray 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 629,999 searches. Data last updated 13 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 151AverageC$ 486FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 179AverageC$ 423FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 187AverageC$ 374FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 188AverageC$ 424FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 198AverageC$ 416FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 208AverageC$ 526FlexibilityNo cancel feeOn-time69%
Search United 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.

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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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