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C$ 200+ 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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
26 Nov — 3 Dec1
1 adult

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 645,034 searches and data was last updated on 21 November 2024.

Fly from

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

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

Nonstop1h 50m

Chicago Midway

Mon 16/12

12:05 p.m.-2:47 p.m.

Nonstop1h 42m

C$ 319

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

2:00 p.m.-2:51 p.m.

Nonstop1h 51m

Chicago O'Hare Intl

Sun 15/12

7:19 a.m.-9:58 a.m.

Nonstop1h 39m

C$ 342

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

6:25 a.m.-10:54 a.m.

1 stop5h 29m

Chicago O'Hare Intl

Mon 16/12

9:50 a.m.-12:31 p.m.

Nonstop1h 41m

C$ 349

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/12

2:05 p.m.-6:36 p.m.

1 stop5h 31m

Chicago O'Hare Intl

Tue 17/12

6:38 p.m.-9:25 p.m.

Nonstop1h 47m

C$ 362

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 12/12

10:25 a.m.-2:45 p.m.

1 stop5h 20m

Chicago O'Hare Intl

Sun 15/12

2:01 p.m.-7:50 p.m.

1 stop4h 49m

C$ 365

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 a.m.-10:30 a.m.

Nonstop1h 50m

Chicago Midway

Sun 15/12

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 366

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

6:52 a.m.-8:05 a.m.

Nonstop2h 13m

Chicago O'Hare Intl

Sun 15/12

7:19 a.m.-9:58 a.m.

Nonstop1h 39m

C$ 372

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/12

6:30 a.m.-6:32 p.m.

1 stop13h 02m

Chicago Midway

Mon 16/12

9:38 a.m.-11:34 p.m.

1 stop12h 56m

C$ 373

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 31/12

6:30 a.m.-2:38 p.m.

1 stop9h 08m

Chicago O'Hare Intl

Thu 16/1

12:35 p.m.-8:31 p.m.

1 stop6h 56m

C$ 398

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 8/12

6:00 a.m.-12:30 p.m.

1 stop7h 30m

Chicago O'Hare Intl

Wed 11/12

6:00 a.m.-11:56 a.m.

1 stop4h 56m

C$ 405

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/11

Showing 1-10 of 39 results
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Flights to Chicago in 2024

Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 645,034 searches and data was last updated on 21 November 2024.

Round-trip from

C$ 319

One-way from

C$ 200

Popular in

November

Cheapest in

April

Average price

C$ 429
Porter Airlines
  • Porter Airlines
  • 12/12-26/12
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 14/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
High demand for flights, 4% potential price rise
Search Deals
Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in November 2024
Search Deals

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 21 November 2024.

Thu 12/123:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 16/1212:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 319
Thu 12/122:00 p.m.YYZ - ORD
Nonstop1h 51mUnited Airlines
Sun 15/127:19 a.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 20/11C$ 342
Thu 12/126:25 a.m.YYZ - ORD
1 stop5h 29mAir Canada
Mon 16/129:50 a.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 19/11C$ 349
Fri 13/122:05 p.m.YYZ - ORD
1 stop5h 31mMultiple Airlines
Tue 17/126:38 p.m.ORD - YYZ
Nonstop1h 47mMultiple Airlines
Deal found 20/11C$ 362
Thu 12/1210:25 a.m.YTZ - ORD
1 stop5h 20mAir Canada
Sun 15/122:01 p.m.ORD - YTZ
1 stop4h 49mAir Canada
Deal found 19/11C$ 365
Thu 12/129:40 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 15/1211:15 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 20/11C$ 366
Thu 12/126:52 a.m.YYZ - ORD
Nonstop2h 13mLufthansa
Sun 15/127:19 a.m.ORD - YYZ
Nonstop1h 39mLufthansa
Deal found 20/11C$ 372
Thu 12/126:30 a.m.YYZ - MDW
1 stop13h 02mWestJet
Mon 16/129:38 a.m.MDW - YYZ
1 stop12h 56mWestJet
Deal found 20/11C$ 373
Tue 31/126:30 a.m.YYZ - ORD
1 stop9h 08mDelta
Thu 16/112:35 p.m.ORD - YYZ
1 stop6h 56mDelta
Deal found 19/11C$ 398
Sun 8/126:00 a.m.YYZ - ORD
1 stop7h 30mAmerican Airlines
Wed 11/126:00 a.m.ORD - YYZ
1 stop4h 56mAmerican Airlines
Deal found 20/11C$ 405
Thu 12/1210:05 a.m.YYZ - MDW
1 stop7h 56mDelta
Mon 16/121:30 p.m.MDW - YYZ
1 stop8h 06mDelta
Deal found 20/11C$ 411
Tue 31/126:15 a.m.YYZ - ORD
Nonstop2h 15mBritish Airways
Tue 7/16:35 p.m.ORD - YYZ
Nonstop1h 45mBritish Airways
Deal found 20/11C$ 415

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 15 November 2024.

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.

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 10 hours 4 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 Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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$ 217

United Airlines

United Airlines

From C$ 249

Porter Airlines

Porter Airlines

From C$ 194

American Airlines

American Airlines

From C$ 250

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 21 November 2024.
Get a feel of what it's like to fly with Lufthansa, American Airlines and Air Canada 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
8,758 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,758 reviews
Delta
8.0
Very good
8,758 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

Porter Airlines
7.8
Good
286 reviews
Delta
8.0
Very good
8,758 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

Air Transat
7.8
Good
389 reviews
Delta
8.0
Very good
8,758 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,172 reviews
Delta
8.0
Very good
8,758 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

WestJet
7.3
Good
2,810 reviews
Delta
8.0
Very good
8,758 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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, American 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$ 89, while round-trip flights cost around C$ 93.

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

    A round-trip flight to Chicago will typically cost around C$ 150, however they can be found for as little as C$ 79.

  • 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).

  • 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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Fly your favourite airline to Chicago

Fly your favourite airline to Chicago. Flight routes are based on user searches made on Cheapflights and were last updated on 21 November 2024.
Air Canada flights from Pearson Intl to O'Hare Intl
United Airlines flights from Pearson Intl to O'Hare Intl
American Airlines flights from Pearson Intl to O'Hare Intl

Fly with Cheapflights

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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.

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