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C$ 189+ Cheap flights to Chicago

— CHI
29 Nov — 6 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 19/114:35 p.m. -
Nonstop2h 05m
Mon 23/116:20 p.m. -
Nonstop1h 45m
Deal found 27/10C$ 298
Thu 19/114:35 p.m. -
Nonstop2h 05m
Sun 22/116:20 p.m. -
Nonstop1h 45m
Deal found 27/10C$ 299
Thu 19/1110:30 a.m. -
Nonstop2h 05m
Sat 21/116:20 p.m. -
Nonstop1h 45m
Deal found 25/10C$ 301
Fri 20/114:35 p.m. -
Nonstop2h 05m
Mon 23/116:20 p.m. -
Nonstop1h 45m
Deal found 26/10C$ 302
Mon 16/114:35 p.m. -
Nonstop2h 05m
Sun 22/116:20 p.m. -
Nonstop1h 45m
Deal found 26/10C$ 305
Fri 20/114:35 p.m. -
Nonstop2h 05m
Sun 22/116:20 p.m. -
Nonstop1h 45m
Deal found 26/10C$ 308
Fri 20/118:00 a.m. -
1 stop8h 00m
Tue 24/1110:15 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 310
Fri 11/122:35 p.m. -
Nonstop2h 03m
Mon 14/1210:05 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 312
Fri 20/114:35 p.m. -
Nonstop2h 05m
Tue 24/116:20 p.m. -
Nonstop1h 45m
Deal found 26/10C$ 312
Sun 22/1112:05 p.m. -
Nonstop2h 15m
Tue 24/111:55 p.m. -
Nonstop1h 47m
Deal found 27/10C$ 313
Fri 27/1110:30 a.m. -
Nonstop2h 05m
Wed 16/1212:15 p.m. -
Nonstop1h 45m
Deal found 25/10C$ 315
Mon 16/114:30 p.m. -
Nonstop2h 13m
Mon 16/118:40 p.m. -
Nonstop1h 43m
Deal found 26/10C$ 319

Find flight deals to Chicago

Round-trip from

C$ 298

One-way from

C$ 189

Popular in

October

Cheapest in

February

Average price

C$ 442

Good round-trip deal

C$ 382 or less

Good one-way deal

C$ 186 or less
Porter Airlines
  • Porter Airlines
  • 19/11-23/11
  • Nonstop
  • 3h 50m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 22/11-31/12
  • Nonstop
  • 2h 05m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 3% 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$ 5 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

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

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 - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 25/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 218

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 4/12

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$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 24/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 26/11

6:00 a.m.-11:25 a.m.

1 stop6h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 3/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 224

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 10/12

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$ 229

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 21/11

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$ 229

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 24/12

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$ 229

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 9 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.

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$ 135
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
468 reviews
Check prices

Entertainment

6.9

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

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
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Entertainment

6.9

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

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
468 reviews
Check prices

Entertainment

6.9

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

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
10,451 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Entertainment

6.9

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

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
11,832 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Entertainment

6.9

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

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
12,210 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Entertainment

6.9

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

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 (1 hour 55 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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