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C$ 180+ Cheap flights to Chicago

— CHI
21 Oct — 28 Oct1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Chicago

Sun 11/1010:10 a.m. -
Nonstop1h 50m
Fri 16/1011:45 a.m. -
Nonstop1h 40m
Deal found 19/9C$ 288
Sat 3/1012:15 p.m. -
Nonstop2h 10m
Sun 4/102:00 p.m. -
Nonstop1h 48m
Deal found 19/9C$ 288
Thu 8/107:00 a.m. -
Nonstop2h 00m
Sun 11/1011:05 a.m. -
1 stop5h 28m
Deal found 20/9C$ 289
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sun 4/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 289
Mon 2/118:20 a.m. -
2 stops7h 40m
Mon 9/111:55 p.m. -
Nonstop1h 47m
Deal found 18/9C$ 289
Fri 2/104:00 p.m. -
1 stop5h 12m
Sun 4/108:40 p.m. -
Nonstop1h 46m
Deal found 18/9C$ 291
Fri 4/1210:35 a.m. -
Nonstop2h 05m
Mon 7/126:20 p.m. -
Nonstop1h 46m
Deal found 19/9C$ 291
Wed 7/1012:25 p.m. -
Nonstop1h 58m
Wed 14/102:15 p.m. -
Nonstop1h 46m
Deal found 20/9C$ 292
Thu 1/1012:15 p.m. -
Nonstop2h 10m
Sun 4/102:00 p.m. -
Nonstop1h 48m
Deal found 16/9C$ 292
Thu 8/1011:00 a.m. -
Nonstop2h 00m
Sun 11/108:50 a.m. -
Nonstop1h 59m
Deal found 20/9C$ 294
Wed 7/101:45 p.m. -
Nonstop1h 50m
Sun 11/1011:45 a.m. -
Nonstop1h 40m
Deal found 16/9C$ 294
Mon 5/101:45 p.m. -
Nonstop1h 50m
Wed 7/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 295

Find flight deals to Chicago

Round-trip from

C$ 288

One-way from

C$ 180

Popular in

October

Cheapest in

February

Average price

C$ 352

Good round-trip deal

C$ 335 or less

Good one-way deal

C$ 234 or less
Porter Airlines
  • Porter Airlines
  • 11/10-16/10
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 3/11-31/12
  • Nonstop
  • 2h 05m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 1% potential increase in price (C$ 6 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Toronto to Chicago.
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Price to beat on a one-way flight from Toronto to Chicago.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 5/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 182

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 10/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 30/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 30/9

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 192

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 21/10

9:00 p.m.-10:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 16/12

12:15 p.m.-6:26 p.m.

1 stop7h 11m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 200

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 17/10

7:00 p.m.-11:21 p.m.

1 stop5h 21m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 200

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 16/10

9:40 a.m.-4:32 p.m.

1 stop7h 52m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 201

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 2/10

12:08 p.m.-6:33 p.m.

1 stop7h 25m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 201

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 10/10

7:00 p.m.-9:00 a.m.

1 stop15h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 207

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/9

Showing 1-10 of 60 resultsSorted by cheapest first
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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

Cheapflights Insights

Everything you need to know about your flight to Chicago

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 7 hours 43 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.

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Friday (78 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (40 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$ 122
United Airlines
United Airlines
From C$ 186
Porter Airlines
Porter Airlines
From C$ 221
WestJet
WestJet
From C$ 177

What are the cheapest airlines that fly to Chicago?

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

Rainfall in Chicago 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

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).

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

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 87 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.

When is the cheapest time to fly to Chicago?

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

Reviews of airlines servicing Chicago

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
462 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Transat
7.7
Good
579 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.4
Good
10,227 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,655 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
American Airlines
7.0
Good
12,077 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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$ 82, while round-trip flights cost around C$ 187.

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

    A round-trip flight to Chicago will typically cost around C$ 300, however they can be found for as little as C$ 187.

  • 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 50 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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