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C$ 148+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 220

One-way from

C$ 148

Popular in

December

Cheapest in

April

Average price

C$ 346

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 26/6-29/6
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/7
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 40 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 June 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 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 29/69:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/6C$ 220
Wed 10/98:15 a.m.YYZ - ORD
Nonstop1h 53mAir Canada
Fri 12/96:20 p.m.ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 12/6C$ 226
Thu 4/92:30 p.m.YYZ - ORD
1 stop6h 18mUnited Airlines
Wed 10/97:15 a.m.ORD - YYZ
1 stop5h 32mUnited Airlines
Deal found 10/6C$ 235
Sat 30/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 12/99:15 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/6C$ 254
Tue 30/93:45 p.m.YYZ - ORD
1 stop5h 42mAmerican Airlines
Thu 2/109:48 a.m.ORD - YYZ
1 stop6h 27mAmerican Airlines
Deal found 10/6C$ 261
Mon 18/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 19/85:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 11/6C$ 280
Sat 4/1010:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Wed 15/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 12/6C$ 283
Thu 3/77:00 a.m.YYZ - ORD
Nonstop1h 59mLufthansa
Mon 7/79:14 p.m.ORD - YYZ
Nonstop1h 44mLufthansa
Deal found 11/6C$ 286
Sun 12/1012:15 p.m.YYZ - ORD
1 stop7h 23mDelta
Sat 18/105:45 p.m.ORD - YYZ
1 stop4h 13mDelta
Deal found 11/6C$ 291
Sat 4/1012:15 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/109:30 a.m.MDW - YYZ
1 stop6h 53mDelta
Deal found 11/6C$ 291
Fri 25/74:00 p.m.YYZ - ORD
1 stop6h 30mMultiple Airlines
Fri 1/86:20 p.m.ORD - YYZ
Nonstop1h 44mMultiple Airlines
Deal found 10/6C$ 340
Mon 21/77:25 p.m.YYZ - ORD
1 stop12h 58mPorter Airlines
Sun 27/75:55 p.m.ORD - YYZ
Nonstop1h 49mPorter Airlines
Deal found 12/6C$ 358

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 12 June 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

Thu 26/6

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

Nonstop1h 50m

Chicago Midway

Sun 29/6

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

Nonstop1h 42m

C$ 220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/9

8:15 a.m.-9:08 a.m.

Nonstop1h 53m

Chicago O'Hare Intl

Fri 12/9

6:20 p.m.-9:02 p.m.

Nonstop1h 42m

C$ 226

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/9

2:30 p.m.-7:48 p.m.

1 stop6h 18m

Chicago O'Hare Intl

Wed 10/9

7:15 a.m.-1:47 p.m.

1 stop5h 32m

C$ 235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/9

3:45 p.m.-8:27 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Thu 2/10

9:48 a.m.-5:15 p.m.

1 stop6h 27m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

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

Nonstop1h 50m

Chicago Midway

Mon 30/6

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/8

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

Nonstop1h 50m

Chicago Midway

Tue 19/8

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

10:25 a.m.-2:55 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Wed 15/10

10:40 a.m.-4:45 p.m.

1 stop5h 05m

C$ 283

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 3/7

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

Nonstop1h 59m

Chicago O'Hare Intl

Mon 7/7

9:14 p.m.-11:58 p.m.

Nonstop1h 44m

C$ 286

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

12:15 p.m.-6:38 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Sat 18/10

5:45 p.m.-10:58 p.m.

1 stop4h 13m

C$ 291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 291

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 40 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 9 June 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 52 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 44 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 (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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$ 207
United Airlines
United Airlines
From C$ 221
Porter Airlines
Porter Airlines
From C$ 170
American Airlines
American Airlines
From C$ 203

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 12 June 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and KLM 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
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
KLM
7.8
Good
1,358 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
396 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost C$ 66, while round-trip flights cost around C$ 94.

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

    A round-trip flight to Chicago will typically cost around C$ 226, 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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