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C$ 182+ Direct flights to Chicago

This is the cheapest price on a non-stop flight to Chicago found by a Cheapflights user in the last 72 hours by searching for a flight departing on 30/3. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
13 Dec — 20 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 13 November 2025.

Thu 8/12:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sat 10/18:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 12/11C$ 258
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
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 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
Fri 28/114:15 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
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
Fri 28/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/11C$ 277
Thu 30/44:50 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sun 3/57:10 a.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 11/11C$ 279
Tue 2/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 4/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 279

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 Fare Finder

 
Use the slider to find non-stop flights to Chicago within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 629,999 searches and data was last updated on 13 November 2025.
Use the filters below to find and compare direct flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 20/3

6:30 p.m.-7:30 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 23/3

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

Nonstop1h 39m

C$ 258

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

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 29/12

4:50 p.m.-5:48 p.m.

Nonstop1h 58m

Chicago O'Hare Intl

Mon 5/1

8:30 p.m.-11:09 p.m.

Nonstop1h 39m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 19/12

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

Nonstop1h 50m

Chicago Midway

Mon 5/1

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

Nonstop1h 42m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 16/1

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

Nonstop1h 50m

Chicago Midway

Sat 17/1

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

Nonstop1h 42m

C$ 268

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/1

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

Nonstop1h 50m

Chicago Midway

Sat 17/1

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

Nonstop1h 42m

C$ 268

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 8/3

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

Nonstop1h 50m

Chicago Midway

Sun 15/3

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

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 11/1

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

Nonstop1h 50m

Chicago Midway

Tue 13/1

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

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 11/1

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/11

Showing 1-10 of 46 results
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Reviews of airlines flying non-stop to Chicago

Get insights into the airlines that provide direct flights 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.
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
389 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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
471 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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
9,017 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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
11,051 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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
10,445 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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.

Temperature and rainfall in Chicago by month

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

CHI

Temperature

-5 - 23 °C

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).

FAQ about direct flights to Chicago

Find answers to frequently asked questions about direct flights to Chicago to unlock the best deals on Cheapflights.

  • How much are direct flights to Chicago?

    On average, a one-way direct flight to Chicago will cost users approximately C$ 468. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,542.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, WestJet, American Airlines, Delta, Air Transat offer direct flights to Chicago. Air Canada is currently the most popular airline that flies direct to Chicago.

  • What is the best time of year to fly direct to Chicago?

    If you're seeking the lowest price on a direct flight to Chicago, April is worth consideration, as prices are usually at their lowest, on average. January may be most appealing to users looking for the quietest time to visit Chicago, when demand is typically at its lowest.

  • What is the most popular direct flight origin to Chicago?

    Currently, the most popular direct flight origin to Chicago is Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 2,145.

See more FAQs

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