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C$ 181+ Cheap flights to Chicago

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 23/11. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

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Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 4 November 2025.

Sun 23/117:14 p.m.YYZ - ORD
1 stop5h 26mAmerican Airlines
Mon 1/125:00 a.m.ORD - YYZ
1 stop5h 03mAmerican Airlines
Deal found 2/11C$ 258
Thu 11/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 258
Thu 4/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 263
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 3/11C$ 264
Wed 19/1111:32 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Tue 25/116:06 a.m.ORD - YYZ
1 stop4h 48mAmerican Airlines
Deal found 3/11C$ 267
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 267
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 268
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Fri 12/126:04 a.m.ORD - YYZ
1 stop9h 31mAmerican Airlines
Deal found 3/11C$ 271
Sat 13/125:16 p.m.YYZ - ORD
1 stop5h 03mAmerican Airlines
Sun 14/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 2/11C$ 272
Thu 11/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Sun 14/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 2/11C$ 274
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 274
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 275

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 4 November 2025.

Round-trip from

C$ 257

One-way from

C$ 181

Popular in

October

Cheapest in

July

Average price

C$ 406

Good round-trip deal

C$ 347 or less

Good one-way deal

C$ 198 or less
Air Canada
  • Air Canada
  • 9/2-28/2
  • 1 total stop
  • 9h 39m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 23/11
  • 1 total stop
  • 7h 29m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 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 Toronto to Chicago.
Search Deals
Price to beat on a one-way flight from Toronto to Chicago.
Search Deals

Cheapflights Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 4 November 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 16/1

11:00 a.m.-12:08 p.m.

Nonstop2h 08m

Chicago O'Hare Intl

Mon 16/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/12

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

Nonstop1h 42m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 17/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Mon 16/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 15/3

9:00 a.m.-10:09 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 18/3

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

C$ 260

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Fri 12/12

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

Nonstop1h 42m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/11

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

Nonstop1h 50m

Chicago Midway

Tue 2/12

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

Nonstop1h 42m

C$ 281

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 20/11

5:30 p.m.-6:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Mon 24/11

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 284

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

3:30 p.m.-4:52 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Sun 30/11

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 284

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 23/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Tue 6/1

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 289

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 25/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Tue 6/1

4:50 p.m.-7:45 p.m.

Nonstop1h 55m

C$ 289

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 60 results
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Best time to book a flight to Chicago

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

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on 31 October 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 6 hours 0 minutes. Flights to Chicago from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 20 October 2024.

Users looking for the lowest fares to Chicago should consider flying on Sunday mornings, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday at noon, when prices are usually at their highest.

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Toronto to Chicago are Air Canada, United Airlines and Porter Airlines.

Air Canada
Air Canada
From C$ 152
United Airlines
United Airlines
From C$ 184
Porter Airlines
Porter Airlines
From C$ 192
WestJet
WestJet
From C$ 179

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, American Airlines and Air Canada.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 4 November 2025.
Read through reviews of airlines serving the United States, such as Porter Airlines,Air Transat, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Overall

8.0

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
387 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Overall

8.0

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 Transat
7.8
Good
470 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Overall

8.0

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
8,998 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Overall

8.0

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
11,038 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Overall

8.0

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
10,400 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Overall

8.0

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.

FAQs about flying to Chicago

  • What is good to know if travelling to Chicago?

    One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water and use sunscreen.

  • Can I find cheaper flights to Chicago if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Chicago?

    Based on reviews from Cheapflights users, Air Canada is rated the highest out of the airlines that fly to Chicago.

  • What is the cheapest airport to fly to in Chicago?

    Chicago O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost C$ 61, while round-trip flights cost around C$ 62.

  • How much is a round-trip flight to Chicago?

    A round-trip flight to Chicago will typically cost around C$ 328, however they can be found for as little as C$ 62.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Toronto offers the quickest one-way flight (1 hour 49 minutes).

  • Does Chicago O'Hare Intl have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl?

    Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).

See more FAQs

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