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C$ 189+ Cheap flights to Chicago

— CHI
25 Nov — 2 Dec1
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

Thu 19/1110:30 a.m. -
Nonstop2h 05m
Sat 21/1112:15 p.m. -
Nonstop1h 45m
Deal found 22/10C$ 301
Tue 1/1210:00 a.m. -
1 stop6h 02m
Wed 6/17:05 a.m. -
1 stop5h 41m
Deal found 22/10C$ 303
Fri 20/1112:05 p.m. -
Nonstop2h 15m
Fri 27/111:55 p.m. -
1 stop5h 01m
Deal found 21/10C$ 303
Tue 1/1210:30 a.m. -
Nonstop2h 05m
Wed 9/126:20 p.m. -
Nonstop1h 45m
Deal found 21/10C$ 304
Fri 20/1110:30 a.m. -
Nonstop2h 05m
Sun 22/116:20 p.m. -
Nonstop1h 45m
Deal found 21/10C$ 305
Thu 3/1210:30 a.m. -
Nonstop2h 05m
Sat 5/1212:15 p.m. -
Nonstop1h 45m
Deal found 22/10C$ 307
Wed 2/124:35 p.m. -
Nonstop2h 05m
Sun 6/1212:15 p.m. -
Nonstop1h 45m
Deal found 21/10C$ 308
Thu 12/118:20 a.m. -
Nonstop2h 03m
Sun 15/118:45 a.m. -
Nonstop1h 42m
Deal found 21/10C$ 310
Sat 5/129:45 a.m. -
1 stop6h 07m
Sat 12/126:20 p.m. -
Nonstop1h 45m
Deal found 21/10C$ 310
Tue 1/1210:30 a.m. -
Nonstop2h 05m
Tue 8/1212:15 p.m. -
Nonstop1h 45m
Deal found 21/10C$ 311
Tue 24/1110:45 a.m. -
1 stop5h 17m
Tue 8/127:20 a.m. -
Nonstop1h 47m
Deal found 22/10C$ 312
Sat 21/118:20 a.m. -
Nonstop2h 03m
Sat 28/111:55 p.m. -
1 stop6h 40m
Deal found 22/10C$ 314

Find flight deals to Chicago

Round-trip from

C$ 301

One-way from

C$ 189

Popular in

October

Cheapest in

February

Average price

C$ 443

Good round-trip deal

C$ 383 or less

Good one-way deal

C$ 186 or less
Porter Airlines
  • Porter Airlines
  • 19/11-21/11
  • Nonstop
  • 3h 50m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 9/12-31/12
  • 1 total stop
  • 5h 47m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
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Average for round-trip flights in October 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 - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 9/12

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 190

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 30/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 25/11

6:45 a.m.-11:07 a.m.

1 stop5h 22m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 22/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 26/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 16/11

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$ 196

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 1/12

10:30 a.m.-11:35 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 203

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 9/12

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 204

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

7:26 p.m.-8:48 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 207

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 5/1

5:55 p.m.-7:01 p.m.

Nonstop2h 06m

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 25/10

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 4 hours 30 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 Saturday (66 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (22 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$ 136
United Airlines
United Airlines
From C$ 189
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 Friday at noon, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday 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
467 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Entertainment

6.9

Overall

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
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Entertainment

6.9

Overall

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
584 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Entertainment

6.9

Overall

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
7.3
Good
10,440 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Entertainment

6.9

Overall

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
11,815 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Entertainment

6.9

Overall

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
7.0
Good
12,191 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Entertainment

6.9

Overall

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, Porter Airlines 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$ 82, while round-trip flights cost around C$ 198.

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

    A round-trip flight to Chicago will typically cost around C$ 198, however they can be found for as little as C$ 198.

  • 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 (2 hours 0 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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