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C$ 183+ Cheap flights to Chicago

— CHI
6 Oct — 13 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

Sat 26/911:00 a.m. -
Nonstop2h 00m
Sun 27/912:59 p.m. -
Nonstop1h 47m
Deal found 5/9C$ 285
Wed 21/1012:15 p.m. -
Nonstop2h 10m
Wed 28/101:55 p.m. -
Nonstop1h 47m
Deal found 6/9C$ 285
Fri 25/98:50 a.m. -
Nonstop1h 58m
Tue 29/99:55 a.m. -
Nonstop1h 45m
Deal found 4/9C$ 286
Tue 13/101:45 p.m. -
Nonstop1h 50m
Tue 20/103:20 p.m. -
Nonstop1h 40m
Deal found 5/9C$ 286
Sat 26/91:00 p.m. -
Nonstop2h 05m
Sun 27/93:40 p.m. -
1 stop5h 13m
Deal found 5/9C$ 288
Tue 27/109:45 a.m. -
1 stop6h 07m
Wed 28/101:55 p.m. -
1 stop6h 41m
Deal found 3/9C$ 288
Fri 2/102:00 p.m. -
Nonstop1h 55m
Mon 5/1011:05 a.m. -
1 stop6h 18m
Deal found 5/9C$ 289
Mon 12/101:45 p.m. -
Nonstop1h 50m
Wed 14/103:20 p.m. -
Nonstop1h 40m
Deal found 5/9C$ 289
Sun 1/114:35 p.m. -
Nonstop2h 05m
Thu 5/116:20 p.m. -
Nonstop1h 46m
Deal found 4/9C$ 289
Fri 25/94:00 p.m. -
Nonstop1h 58m
Sun 27/98:40 p.m. -
Nonstop1h 46m
Deal found 4/9C$ 291
Wed 4/1110:45 a.m. -
1 stop5h 07m
Mon 9/111:55 p.m. -
Nonstop1h 47m
Deal found 4/9C$ 291
Fri 25/91:00 p.m. -
Nonstop2h 05m
Sun 27/93:40 p.m. -
1 stop6h 38m
Deal found 2/9C$ 292

Find flight deals to Chicago

Round-trip from

C$ 285

One-way from

C$ 183

Popular in

October

Cheapest in

February

Average price

C$ 365

Good round-trip deal

C$ 285 or less

Good one-way deal

C$ 191 or less
Lufthansa
  • Lufthansa
  • 26/9-27/9
  • Nonstop
  • 3h 47m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 14/10-31/12
  • Nonstop
  • 1h 58m 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$ 3 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

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 13/10

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$ 184

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 2/10

12:08 p.m.-6:26 p.m.

1 stop7h 18m

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 30/9

9:45 a.m.-4:13 p.m.

1 stop7h 28m

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

Sat 28/11

12:15 p.m.-6:30 p.m.

1 stop7h 15m

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 30/9

12:05 p.m.-8:12 p.m.

2 stops9h 07m

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

Wed 30/9

12:45 p.m.-6:41 p.m.

1 stop6h 56m

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

Fri 6/11

9:44 a.m.-3:13 p.m.

1 stop6h 29m

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

Mon 5/10

2:24 p.m.-8:30 p.m.

1 stop7h 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 - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/9

2:24 p.m.-6:33 p.m.

1 stop5h 09m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 12/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 199

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

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 24 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 (75 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (32 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
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Transat
7.8
Good
576 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,173 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
American Airlines
7.1
Good
12,041 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,593 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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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