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C$ 188+ 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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
25 Feb — 4 Mar1
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 20 February 2025.

Round-trip from

C$ 290

One-way from

C$ 188

Popular in

December

Cheapest in

April

Average price

C$ 405

Good round-trip deal

C$ 282 or less

Good one-way deal

C$ 175 or less
Porter Airlines
  • Porter Airlines
  • 20/3-24/3
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 29/4
  • 1 total stop
  • 5h 22m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in February 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 20 February 2025.

Thu 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/35:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/2C$ 290
Fri 30/57:25 a.m.YTZ - ORD
1 stop4h 59mAir Canada
Mon 2/610:40 a.m.ORD - YTZ
1 stop6h 10mAir Canada
Deal found 18/2C$ 296
Fri 6/62:00 p.m.YYZ - ORD
1 stop5h 53mAir Canada
Sun 8/610:40 a.m.ORD - YYZ
1 stop6h 18mAir Canada
Deal found 19/2C$ 304
Sat 22/37:55 p.m.YYZ - ORD
1 stop13h 40mMultiple Airlines
Tue 25/36:25 p.m.ORD - YYZ
2 stops28h 30mMultiple Airlines
Deal found 19/2C$ 318
Mon 17/39:30 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Thu 20/35:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 19/2C$ 325
Sat 12/46:30 a.m.YYZ - MDW
1 stop13h 03mWestJet
Sun 20/410:20 a.m.MDW - YYZ
1 stop24h 14mWestJet
Deal found 20/2C$ 347
Sun 4/58:15 a.m.YYZ - ORD
Nonstop1h 55mUnited Airlines
Sun 4/58:25 p.m.ORD - YYZ
Nonstop1h 42mUnited Airlines
Deal found 19/2C$ 351
Thu 20/310:20 a.m.YYZ - MDW
1 stop3h 16mDelta
Mon 24/32:55 p.m.MDW - YYZ
1 stop6h 43mDelta
Deal found 19/2C$ 351
Fri 18/49:45 a.m.YYZ - ORD
1 stop7h 23mDelta
Sat 19/45:00 p.m.ORD - YYZ
1 stop4h 55mDelta
Deal found 20/2C$ 359
Fri 18/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 19/412:55 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 20/2C$ 361
Sat 3/51:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 10/59:45 a.m.ORD - YYZ
1 stop6h 35mAmerican Airlines
Deal found 19/2C$ 367
Sun 16/36:30 a.m.YYZ - ORD
1 stop16h 17mWestJet
Sat 22/37:10 p.m.ORD - YYZ
1 stop17h 23mWestJet
Deal found 18/2C$ 378

Find flights to Chicago within your budget

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 February 2025.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/3

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

Mon 24/3

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 30/5

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

1 stop4h 59m

Chicago O'Hare Intl

Mon 2/6

10:40 a.m.-5:50 p.m.

1 stop6h 10m

C$ 296

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/6

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Sun 8/6

10:40 a.m.-5:58 p.m.

1 stop6h 18m

C$ 304

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 22/3

7:55 p.m.-8:35 a.m.

1 stop13h 40m

Chicago O'Hare Intl

Tue 25/3

6:25 p.m.-11:55 p.m.

2 stops28h 30m

C$ 318

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/3

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Thu 20/3

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 325

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/4

6:30 a.m.-6:33 p.m.

1 stop13h 03m

Chicago Midway

Sun 20/4

10:20 a.m.-11:34 a.m.

1 stop24h 14m

C$ 347

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 4/5

8:15 a.m.-9:10 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 5/5

1:00 p.m.-3:46 p.m.

Nonstop1h 46m

C$ 351

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

Chicago Midway

Mon 24/3

2:55 p.m.-10:38 p.m.

1 stop6h 43m

C$ 351

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

9:45 a.m.-4:08 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Sat 19/4

5:00 p.m.-10:55 p.m.

1 stop4h 55m

C$ 359

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 18/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Sat 19/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

C$ 361

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/2

Showing 1-10 of 36 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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 14 February 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 5 hours 36 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 (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 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$ 221

United Airlines

United Airlines

From C$ 246

Porter Airlines

Porter Airlines

From C$ 188

American Airlines

American Airlines

From C$ 249

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, Air Canada and United 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 February 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines 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.
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,227 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
380 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,768 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

  • 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, WestJet 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$ 52, while round-trip flights cost around C$ 27.

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

    A round-trip flight to Chicago will typically cost around C$ 671, however they can be found for as little as C$ 19.

  • 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).

  • 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).

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