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C$ 168+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 23/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
29 Mar — 5 Apr1
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
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 27 February 2026.

Sat 6/68:05 a.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Wed 10/68:20 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 26/2C$ 259
Sat 21/311:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 25/2C$ 259
Fri 10/48:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 12/49:20 p.m.
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 27/2C$ 260
Wed 18/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 25/2C$ 260
Tue 7/410:15 a.m.
YYZ
-
ORD
Nonstop2h 03m
United Airlines
Tue 7/44:43 p.m.
ORD
-
YYZ
Nonstop1h 54m
United Airlines
Deal found 24/2C$ 261
Wed 11/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 13/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 24/2C$ 261
Fri 5/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Mon 8/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 24/2C$ 261
Mon 9/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 11/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 23/2C$ 263
Thu 26/37:00 a.m.
YYZ
-
ORD
1 stop5h 18m
Air Canada
Sun 29/38:20 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 23/2C$ 264
Sat 28/311:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 23/2C$ 264
Sun 12/46:45 a.m.
YTZ
-
ORD
1 stop5h 08m
Air Canada
Sun 19/412:50 p.m.
ORD
-
YTZ
1 stop6h 02m
Air Canada
Deal found 26/2C$ 264
Thu 9/42:15 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Mon 13/43:45 p.m.
ORD
-
YYZ
1 stop7h 09m
Air Canada
Deal found 24/2C$ 265

Find flight deals to Chicago

Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 27 February 2026.

Round-trip from

C$ 259

One-way from

C$ 168

Popular in

February

Cheapest in

July

Average price

C$ 395

Good round-trip deal

C$ 285 or less

Good one-way deal

C$ 270 or less
Air Canada
  • Air Canada
  • 6/6-10/6
  • Nonstop
  • 3h 43m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 14/4
  • Nonstop
  • 1h 55m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 27 February 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 12/4

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

Nonstop1h 39m

C$ 272

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 8/6

10:45 a.m.-2:53 p.m.

1 stop5h 08m

Chicago O'Hare Intl

Wed 10/6

2:00 p.m.-4:41 p.m.

Nonstop1h 41m

C$ 293

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/3

12:45 p.m.-5:01 p.m.

1 stop5h 16m

Chicago O'Hare Intl

Sun 15/3

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Tue 7/4

3:35 p.m.-10:23 p.m.

1 stop5h 48m

C$ 300

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 30/3

11:00 a.m.-12:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Mon 6/4

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

Nonstop1h 39m

C$ 300

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 5/4

8:00 a.m.-7:02 p.m.

1 stop10h 02m

C$ 300

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/3

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Fri 3/4

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

1 stop6h 47m

C$ 300

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 23/4

11:00 a.m.-12:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 26/4

4:43 p.m.-7:37 p.m.

Nonstop1h 54m

C$ 300

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 18/3

10:05 a.m.-12:29 p.m.

1 stop3h 24m

Chicago Midway

Mon 30/3

6:34 p.m.-10:39 p.m.

1 stop3h 05m

C$ 301

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/3

3:59 p.m.-8:17 p.m.

1 stop5h 18m

Chicago O'Hare Intl

Fri 3/4

5:40 p.m.-10:39 p.m.

1 stop3h 59m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on 20 February 2026.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 78 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.

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 5 hours 14 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.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 21 February 2026.

Users looking for the lowest fares to Chicago should consider flying on Monday mornings, when prices are typically cheapest. Budget-minded travellers will want to avoid Saturday evenings, when prices are usually at their highest.

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (62 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$ 148
Porter Airlines
Porter Airlines
From C$ 112
WestJet
WestJet
From C$ 173

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, American Airlines and Air Canada.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals 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

Plan your trip to Chicago by taking into account the average temperature totals 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).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 27 February 2026.
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
419 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
419 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Transat
7.7
Good
514 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
United Airlines
7.4
Good
9,352 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
American Airlines
7.2
Good
11,359 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Canada
7.1
Good
10,750 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost C$ 67, while round-trip flights cost around C$ 114.

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

    A round-trip flight to Chicago will typically cost around C$ 239, however they can be found for as little as C$ 114.

  • 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

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