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C$ 182+ Cheap flights to Chicago

— CHI
12 Oct — 19 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

Fri 25/911:00 a.m. -
Nonstop2h 00m
Sun 27/99:55 a.m. -
Nonstop1h 45m
Deal found 11/9C$ 284
Thu 24/911:00 a.m. -
Nonstop2h 00m
Sun 27/97:09 a.m. -
Nonstop1h 45m
Deal found 10/9C$ 285
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 9/9C$ 285
Thu 24/910:45 a.m. -
1 stop5h 07m
Thu 1/102:00 p.m. -
Nonstop1h 48m
Deal found 10/9C$ 285
Fri 25/91:45 p.m. -
Nonstop1h 50m
Fri 2/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 287
Thu 24/97:35 p.m. -
Nonstop2h 06m
Sun 27/97:25 a.m. -
Nonstop1h 42m
Deal found 10/9C$ 287
Sat 26/96:50 p.m. -
Nonstop1h 58m
Mon 28/93:40 p.m. -
1 stop6h 38m
Deal found 10/9C$ 288
Wed 23/91:45 p.m. -
Nonstop1h 50m
Mon 28/911:45 a.m. -
Nonstop1h 40m
Deal found 9/9C$ 288
Thu 24/97:35 p.m. -
Nonstop2h 06m
Mon 28/97:25 a.m. -
Nonstop1h 42m
Deal found 10/9C$ 288
Thu 24/912:25 p.m. -
Nonstop1h 58m
Sun 27/93:40 p.m. -
1 stop6h 38m
Deal found 9/9C$ 290
Tue 20/1010:10 a.m. -
Nonstop1h 50m
Wed 21/1011:45 a.m. -
Nonstop1h 40m
Deal found 8/9C$ 290
Fri 16/102:00 p.m. -
Nonstop1h 55m
Sun 18/109:55 a.m. -
Nonstop1h 45m
Deal found 8/9C$ 291

Find flight deals to Chicago

Round-trip from

C$ 284

One-way from

C$ 182

Popular in

October

Cheapest in

February

Average price

C$ 366

Good round-trip deal

C$ 286 or less

Good one-way deal

C$ 191 or less
Air Canada
  • Air Canada
  • 25/9-27/9
  • Nonstop
  • 3h 45m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 29/10-31/12
  • 1 total stop
  • 5h 07m 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. 0% potential price decrease (C$ 4 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

Thu 1/10

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

Wed 23/9

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

Tue 20/10

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$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 29/9

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$ 184

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 16/10

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$ 184

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 22/10

2:00 p.m.-2:55 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 193

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 7/10

12:15 p.m.-1:25 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 193

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 12/10

8:50 a.m.-9:48 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 198

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 1/10

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 198

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 13/12

8:35 a.m.-9:44 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 200

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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 5 hours 26 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 Wednesday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (49 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$ 121
United Airlines
United Airlines
From C$ 184
Porter Airlines
Porter Airlines
From C$ 218
WestJet
WestJet
From C$ 175

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 Friday at noon, 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
460 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
460 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
460 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
10,208 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
7.1
Good
12,050 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
11,615 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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 Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost C$ 81, while round-trip flights cost around C$ 185.

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

    A round-trip flight to Chicago will typically cost around C$ 429, however they can be found for as little as C$ 185.

  • 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).

  • Which airport is closest to Athenaeum Center for Thought & Culture?

    If being close to Athenaeum Center for Thought & Culture is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

  • 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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