Find flights
Deals
Airlines

C$ 179+ 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 16/7. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
4 Jul — 11 Jul1
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 4 June 2026.

Thu 16/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 19/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/5C$ 280
Sat 13/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 14/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/5C$ 282
Tue 1/910:05 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 6/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 31/5C$ 282
Mon 15/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 23/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 1/6C$ 284
Thu 25/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 28/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/6C$ 286
Fri 4/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 6/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/6C$ 286
Wed 24/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 27/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/6C$ 287
Tue 1/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Tue 8/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/5C$ 287
Sun 14/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 17/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/5C$ 288
Thu 10/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 13/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/6C$ 288
Thu 3/910:05 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 6/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 31/5C$ 290
Sat 5/910:05 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sat 5/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/6C$ 291

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 4 June 2026.

Round-trip from

C$ 280

One-way from

C$ 179

Popular in

May

Cheapest in

July

Average price

C$ 338

Good round-trip deal

C$ 294 or less

Good one-way deal

C$ 203 or less
Porter Airlines
  • Porter Airlines
  • 16/7-19/7
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 2/7
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 4 June 2026.
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 - MDW

YTZMDW

Toronto Island

Sat 13/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

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

Nonstop1h 40m

C$ 287

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 20/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 30/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Thu 2/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 298

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 8/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 305

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 305

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 25/6

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 28/6

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 318

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 30/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Fri 3/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 318

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Wed 1/7

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

Nonstop1h 40m

C$ 341

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 17/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

Chicago Midway

Sat 20/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 365

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 18/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

Chicago Midway

Sun 21/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 365

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/5

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
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

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 6 hours 10 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 Monday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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$ 150
Porter Airlines
Porter Airlines
From C$ 114
WestJet
WestJet
From C$ 176

What are the cheapest airlines that fly to Chicago?

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

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).

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?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 30 May 2026.

Users looking for the lowest fares to Chicago should consider flying on Wednesday afternoons, 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

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 4 June 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
440 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
440 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Transat
7.8
Good
554 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
United Airlines
7.4
Good
9,774 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
American Airlines
7.1
Good
11,642 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,126 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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$ 81, while round-trip flights cost around C$ 162.

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

    A round-trip flight to Chicago will typically cost around C$ 549, however they can be found for as little as C$ 162.

  • 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 Wrigley Field?

    If being close to Wrigley Field 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.