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C$ 141+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
22 abr. — 29 abr.1
1 adult

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 17 abril 2025.

Round-trip from

C$ 270

One-way from

C$ 171

Popular in

December

Cheapest in

April

Average price

C$ 345

Good round-trip deal

C$ 266 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 10/5-5/9
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 6/5
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 25 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in April 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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Find flight deals to Chicago

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 17 abril 2025.

sáb. 10/57:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
vie. 5/99:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/4C$ 270
dom. 1/62:10 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
dom. 8/610:00 a.m.ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 17/4C$ 279
jue. 22/59:00 p.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
lun. 26/58:25 p.m.ORD - YYZ
Nonstop1h 42mMultiple Airlines
Deal found 17/4C$ 283
jue. 22/57:25 a.m.YTZ - ORD
1 stop4h 59mAir Canada
jue. 29/52:16 p.m.ORD - YTZ
1 stop5h 21mAir Canada
Deal found 17/4C$ 290
sáb. 10/57:55 a.m.YYZ - ORD
Nonstop1h 55mUnited Airlines
vie. 5/99:12 p.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 17/4C$ 298
sáb. 31/57:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
sáb. 7/69:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 16/4C$ 302
mar. 6/53:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
mié. 14/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/4C$ 305
sáb. 31/59:49 a.m.YYZ - MDW
1 stop3h 39mDelta
sáb. 7/65:25 p.m.MDW - YYZ
1 stop4h 33mDelta
Deal found 16/4C$ 326
mar. 6/56:08 p.m.YYZ - ORD
1 stop3h 37mDelta
dom. 11/56:24 a.m.ORD - YYZ
1 stop4h 16mDelta
Deal found 17/4C$ 327
jue. 22/56:30 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
sáb. 31/512:08 p.m.ORD - YYZ
1 stop5h 27mAmerican Airlines
Deal found 16/4C$ 347
sáb. 17/56:20 p.m.YYZ - ORD
Nonstop1h 55mBritish Airways
sáb. 24/53:00 p.m.ORD - YYZ
Nonstop1h 35mBritish Airways
Deal found 17/4C$ 367
vie. 2/511:00 a.m.YYZ - ORD
Nonstop2h 03mLufthansa
dom. 4/56:01 p.m.ORD - YYZ
Nonstop1h 43mLufthansa
Deal found 17/4C$ 376

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 17 abril 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

sáb. 10/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

vie. 5/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 270

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 1/6

2:10 p.m.-3:05 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

dom. 8/6

10:00 a.m.-12:42 p.m.

Nonstop1h 42m

C$ 279

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 22/5

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

Nonstop2h 05m

Chicago O'Hare Intl

lun. 26/5

8:25 p.m.-11:07 p.m.

Nonstop1h 42m

C$ 283

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

jue. 22/5

7:25 a.m.-11:24 a.m.

1 stop4h 59m

Chicago O'Hare Intl

jue. 29/5

2:16 p.m.-8:37 p.m.

1 stop5h 21m

C$ 290

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

sáb. 10/5

7:55 a.m.-8:50 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

vie. 5/9

9:12 p.m.-11:58 p.m.

Nonstop1h 46m

C$ 298

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 31/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

sáb. 7/6

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 302

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 6/5

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

mié. 14/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 305

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 31/5

12:15 p.m.-4:21 p.m.

1 stop5h 06m

Chicago Midway

sáb. 7/6

5:25 p.m.-10:58 p.m.

1 stop4h 33m

C$ 326

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 6/5

6:08 p.m.-8:45 p.m.

1 stop3h 37m

Chicago O'Hare Intl

dom. 11/5

6:24 a.m.-11:40 a.m.

1 stop4h 16m

C$ 327

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 22/5

6:30 a.m.-7:25 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

mar. 27/5

7:00 a.m.-5:20 p.m.

1 stop9h 20m

C$ 347

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/4

Showing 1-10 of 42 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 11 April 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 81 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 52 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 30 June 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 Thursday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 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$ 218

United Airlines

United Airlines

From C$ 239

Porter Airlines

Porter Airlines

From C$ 188

American Airlines

American Airlines

From C$ 230

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 17 abril 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and Air Transat to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
281 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,916 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,667 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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, Delta 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$ 94, while round-trip flights cost around C$ 96.

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

    A round-trip flight to Chicago will typically cost around C$ 118, however they can be found for as little as C$ 69.

  • 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 49 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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