Find flights
Deals
Airlines

C$ 183+ Cheap flights to Chicago

— CHI
21 Sep — 28 Sep1
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 24/910:30 a.m. -
1 stop5h 22m
Mon 28/99:55 a.m. -
Nonstop1h 45m
Deal found 18/8C$ 277
Wed 9/910:10 a.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 18/8C$ 278
Thu 24/97:35 p.m. -
Nonstop2h 06m
Mon 28/97:25 a.m. -
Nonstop1h 42m
Deal found 17/8C$ 278
Thu 10/92:00 p.m. -
Nonstop1h 55m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 19/8C$ 279
Thu 17/910:10 a.m. -
Nonstop1h 50m
Sat 19/93:20 p.m. -
Nonstop1h 40m
Deal found 21/8C$ 279
Fri 25/912:15 p.m. -
Nonstop2h 06m
Mon 28/97:25 a.m. -
Nonstop1h 42m
Deal found 18/8C$ 279
Fri 11/92:00 p.m. -
Nonstop1h 55m
Sun 27/99:55 a.m. -
Nonstop1h 45m
Deal found 19/8C$ 281
Thu 10/912:15 p.m. -
Nonstop2h 06m
Sun 13/97:25 a.m. -
Nonstop1h 42m
Deal found 17/8C$ 281
Thu 10/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 18/8C$ 282
Fri 11/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 17/8C$ 283
Fri 18/910:10 a.m. -
Nonstop1h 50m
Tue 22/911:45 a.m. -
Nonstop1h 40m
Deal found 17/8C$ 285
Fri 11/99:00 a.m. -
1 stop6h 52m
Mon 28/95:35 p.m. -
Nonstop1h 43m
Deal found 19/8C$ 286

Find flight deals to Chicago

Round-trip from

C$ 277

One-way from

C$ 183

Popular in

July

Cheapest in

February

Average price

C$ 359

Good round-trip deal

C$ 281 or less

Good one-way deal

C$ 191 or less
Air Canada
  • Air Canada
  • 24/9-28/9
  • 1 total stop
  • 7h 07m total
  • Toronto to Chicago
Search Deals
United Airlines
  • United Airlines
  • 18/9
  • Nonstop
  • 2h 03m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Toronto to Chicago.
Search Deals
Price to beat on a one-way flight from Toronto to Chicago.
Search Deals

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

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 24/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Sun 27/9

10:43 a.m.-1:42 p.m.

Nonstop1h 59m

C$ 292

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 13/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Sat 26/9

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 292
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

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

Nonstop1h 50m

Chicago Midway

Mon 21/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 318

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 12/9

7:00 p.m.-12:28 a.m.

1 stop6h 28m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-11:18 p.m.

1 stop6h 38m

C$ 325

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

2:45 p.m.-3:51 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sat 19/9

6:00 a.m.-1:47 p.m.

1 stop6h 47m

C$ 330

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 25/9

10:15 a.m.-11:21 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Tue 29/9

8:50 a.m.-2:19 p.m.

1 stop4h 29m

C$ 330

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 21/9

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Thu 24/9

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 27/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Wed 30/9

5:00 a.m.-11:43 a.m.

1 stop5h 43m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 19/9

1:00 p.m.-2:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 26/9

7:30 a.m.-1:47 p.m.

1 stop5h 17m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 20/9

6:00 a.m.-10:37 a.m.

1 stop5h 37m

Chicago O'Hare Intl

Thu 24/9

8:55 a.m.-1:34 p.m.

1 stop3h 39m

C$ 339

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/8

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 6 hours 25 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 Saturday, which is when the least amount of flights are scheduled (33 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$ 120
United Airlines
United Airlines
From C$ 183
WestJet
WestJet
From C$ 174
Porter Airlines
Porter Airlines
From C$ 217

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
457 reviews
Check prices

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

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
457 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

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
573 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

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
10,113 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

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
11,990 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

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
11,517 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

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$ 142, while round-trip flights cost around C$ 204.

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

    A round-trip flight to Chicago will typically cost around C$ 858, however they can be found for as little as C$ 93.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Fly with Cheapflights

How does Cheapflights help users find flights to Chicago?

Cheapflights makes it easy to find Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights to Chicago.

Can Cheapflights find flights to Chicago with no change fees?

Yes, we can. To see specific flights to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Chicago flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.