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C$ 175+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
19 Nov — 26 Nov1
1 adult
1 adult, Economy

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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 20 October 2025.

Sat 8/1110:57 a.m.YYZ - ORD
1 stop9h 32mAmerican Airlines
Fri 14/115:00 a.m.ORD - YYZ
1 stop5h 14mAmerican Airlines
Deal found 19/10C$ 257
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/122:55 p.m.ORD - YYZ
Nonstop1h 49mAmerican Airlines
Deal found 18/10C$ 264
Thu 4/1211:36 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Mon 8/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 20/10C$ 265
Tue 18/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Tue 25/116:06 a.m.ORD - YYZ
1 stop4h 48mAmerican Airlines
Deal found 19/10C$ 271
Tue 2/1211:59 a.m.YYZ - ORD
1 stop4h 57mAmerican Airlines
Tue 9/121:11 p.m.ORD - YYZ
1 stop4h 50mAmerican Airlines
Deal found 18/10C$ 273
Tue 2/125:15 p.m.YYZ - ORD
1 stop4h 50mAmerican Airlines
Thu 4/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 20/10C$ 279
Tue 25/116:05 a.m.YYZ - ORD
1 stop4h 56mDelta
Fri 28/116:45 a.m.ORD - YYZ
1 stop3h 39mDelta
Deal found 18/10C$ 282
Tue 25/119:52 a.m.YYZ - MDW
1 stop3h 42mDelta
Fri 28/119:41 a.m.MDW - YYZ
1 stop5h 21mDelta
Deal found 18/10C$ 282
Mon 10/115:15 p.m.YYZ - ORD
1 stop5h 08mAmerican Airlines
Thu 13/117:10 a.m.ORD - YYZ
1 stop7h 47mAmerican Airlines
Deal found 19/10C$ 285
Thu 4/126:05 a.m.YYZ - MDW
1 stop3h 49mKLM
Mon 8/126:40 p.m.MDW - YYZ
1 stop3h 31mKLM
Deal found 20/10C$ 285
Mon 24/114:30 p.m.YYZ - ORD
1 stop8h 07mAmerican Airlines
Fri 28/115:00 a.m.ORD - YYZ
1 stop5h 03mAmerican Airlines
Deal found 18/10C$ 286
Thu 18/129:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 7/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 19/10C$ 287

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, 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 20 October 2025.

Round-trip from

C$ 242

One-way from

C$ 175

Popular in

October

Cheapest in

July

Average price

C$ 408

Good round-trip deal

C$ 296 or less

Good one-way deal

C$ 149 or less
American Airlines
  • American Airlines
  • 24/3-31/3
  • 1 total stop
  • 9h 33m total
  • Toronto to Chicago
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American Airlines
  • American Airlines
  • 3/12
  • 1 total stop
  • 5h 36m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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

 
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 20 October 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 25/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 245

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 8/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sat 11/4

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 250

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 15/3

9:00 a.m.-10:09 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 18/3

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 276

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 25/11

6:05 a.m.-10:01 a.m.

1 stop4h 56m

Chicago O'Hare Intl

Fri 28/11

6:45 a.m.-11:24 a.m.

1 stop3h 39m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 9/11

6:05 a.m.-10:01 a.m.

1 stop4h 56m

Chicago O'Hare Intl

Sat 15/11

10:46 a.m.-5:15 p.m.

1 stop5h 29m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 20/11

6:05 a.m.-10:01 a.m.

1 stop4h 56m

Chicago O'Hare Intl

Sat 29/11

6:45 a.m.-11:24 a.m.

1 stop3h 39m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/11

6:05 p.m.-8:29 p.m.

1 stop3h 24m

Chicago O'Hare Intl

Mon 17/11

2:35 p.m.-11:05 p.m.

1 stop7h 30m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 9/11

6:05 a.m.-10:01 a.m.

1 stop4h 56m

Chicago O'Hare Intl

Fri 14/11

5:08 p.m.-11:05 p.m.

1 stop4h 57m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 8/11

6:15 a.m.-9:12 a.m.

1 stop3h 57m

Chicago O'Hare Intl

Mon 17/11

2:35 p.m.-11:05 p.m.

1 stop7h 30m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/10

Showing 1-10 of 60 results
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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
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 17 October 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 77 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 6 hours 31 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 20 October 2024.

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

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (68 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (58 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$ 151
United Airlines
United Airlines
From C$ 184
Porter Airlines
Porter Airlines
From C$ 192
WestJet
WestJet
From C$ 179

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).

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 20 October 2025.
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
381 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
381 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Transat
7.8
Good
466 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,991 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,026 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,334 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Food

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost C$ 62, while round-trip flights cost around C$ 62.

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

    A round-trip flight to Chicago will typically cost around C$ 99, however they can be found for as little as C$ 44.

  • 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

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