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C$ 183+ 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 15/3. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
6 Dec — 13 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 6 November 2025.

Sat 17/112:05 p.m.YYZ - ORD
Nonstop1h 56mAir Canada
Mon 16/28:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 260
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 265
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 11/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 265
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 271
Thu 20/116:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 272
Sat 13/1211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 15/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 272
Thu 11/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Mon 15/122:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 274
Fri 9/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/11C$ 274
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 275
Thu 20/116:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Wed 26/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 5/11C$ 276
Thu 20/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 26/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/11C$ 276
Wed 19/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 22/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/11C$ 278

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 6 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

YTZ - MDW

YTZMDW

Toronto Island

Sat 13/12

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Thu 15/1

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

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/3

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

Nonstop1h 50m

Chicago Midway

Tue 17/3

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

Nonstop1h 42m

C$ 274

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 5/12

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 7/12

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

Nonstop1h 39m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 6/12

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sun 7/12

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

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 19/11

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

Nonstop1h 50m

Chicago Midway

Sat 22/11

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

Nonstop1h 42m

C$ 278

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 18/11

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

Nonstop2h 22m

Chicago O'Hare Intl

Wed 26/11

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

Nonstop1h 39m

C$ 285

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 18/11

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

Nonstop2h 22m

Chicago O'Hare Intl

Sun 23/11

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 285

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$ 285

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 28/11

11:00 a.m.-12:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 30/11

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 285

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 21/11

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$ 285

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 6 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

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

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
387 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

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
470 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

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
9,003 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

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
11,040 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

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
10,412 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

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$ 471. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,553.

  • 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$ 2,160.

See more FAQs

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