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C$ 130+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
9 Nov — 16 Nov1
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 503,521 searches and data was last updated on 4 November 2024.

Fly from

Any airport

Route

Depart

Return

Price

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 27/12

5:35 p.m.-10:13 p.m.

1 stop5h 38m

C$ 190

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/12

10:00 a.m.-9:07 p.m.

1 stop12h 07m

C$ 195

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/12

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

Nonstop1h 50m

C$ 195

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/12

3:30 p.m.-4:29 p.m.

Nonstop1h 59m

C$ 201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 8/12

6:30 a.m.-11:39 a.m.

1 stop6h 09m

C$ 225

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 4/2

11:10 a.m.-12:00 p.m.

Nonstop1h 50m

C$ 226

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 22/11

6:15 a.m.-7:30 a.m.

Nonstop2h 15m

C$ 229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 11/2

6:20 p.m.-7:20 p.m.

Nonstop2h 00m

C$ 241

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/12

2:55 p.m.-10:14 p.m.

1 stop8h 19m

C$ 248

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 11/2

3:00 p.m.-10:55 p.m.

1 stop8h 55m

C$ 197

Flights are sorted by cheapest first

Deals found on 4/11

Showing 1-10 of 37 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 503,521 searches and data was last updated on 4 November 2024.

Round-trip from

C$ 290

One-way from

C$ 130

Popular in

November

Cheapest in

April

Average price

C$ 421
Porter Airlines
  • Porter Airlines
  • 25/12-25/1
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 12/2
  • 1 total stop
  • 5h 45m total
  • Toronto to Chicago
Search Deals
High demand for flights, 5% potential price rise
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Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in November 2024
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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 4 November 2024.

Thu 28/113:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 2/125:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 314
Thu 28/113:30 p.m.YYZ - ORD
Nonstop1h 59mUnited Airlines
Mon 2/128:25 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 3/11C$ 333
Fri 29/112:05 p.m.YYZ - ORD
1 stop5h 31mAir Canada
Sun 1/127:19 a.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 3/11C$ 340
Sat 23/118:50 a.m.YTZ - ORD
1 stop5h 08mAir Canada
Sat 30/112:00 p.m.ORD - YTZ
1 stop5h 43mAir Canada
Deal found 2/11C$ 340
Thu 28/119:30 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Mon 2/125:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 3/11C$ 347
Thu 28/115:30 p.m.YYZ - ORD
Nonstop2h 07mLufthansa
Mon 2/128:25 p.m.ORD - YYZ
Nonstop1h 41mLufthansa
Deal found 3/11C$ 351
Wed 4/124:30 p.m.YTZ - ORD
1 stop9h 04mMultiple Airlines
Wed 11/124:19 p.m.ORD - YTZ
1 stop15h 11mMultiple Airlines
Deal found 4/11C$ 364
Sat 23/119:00 a.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
Wed 25/121:55 p.m.ORD - YYZ
1 stop6h 40mMultiple Airlines
Deal found 3/11C$ 368
Tue 3/1212:15 p.m.YYZ - MDW
1 stop5h 47mDelta
Tue 10/129:30 a.m.MDW - YYZ
1 stop6h 07mDelta
Deal found 4/11C$ 374
Wed 27/116:15 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Tue 3/125:00 a.m.ORD - YYZ
1 stop5h 00mAmerican Airlines
Deal found 4/11C$ 388
Tue 3/126:30 a.m.YYZ - MDW
1 stop8h 05mWestJet
Tue 10/122:15 p.m.MDW - YYZ
1 stop8h 19mWestJet
Deal found 3/11C$ 423
Sat 14/126:00 a.m.YYZ - ORD
1 stop11h 35mWestJet
Sun 15/127:05 a.m.ORD - YYZ
1 stop3h 22mWestJet
Deal found 4/11C$ 428

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 1 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.

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How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 11 hours 5 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.

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Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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$ 249

Porter Airlines

Porter Airlines

From C$ 194

American Airlines

American Airlines

From C$ 257

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 4 November 2024.
Get a feel of what it's like to fly with Air Canada, Lufthansa and Delta 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
8,829 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

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
8,829 reviews
Delta
8.0
Very good
8,829 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

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
387 reviews
Delta
8.0
Very good
8,829 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

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

Porter Airlines
7.7
Good
293 reviews
Delta
8.0
Very good
8,829 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

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
9,226 reviews
Delta
8.0
Very good
8,829 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

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
2,803 reviews
Delta
8.0
Very good
8,829 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

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

  • When is the best time to fly to Chicago?

    Peak Season: Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the Lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighbourhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals. Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavours accompanied by live music. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers. September can be the most enjoyable and mild month of the year but there’s less going on during this period. Off-peak Season: January to March is when Chicago is least busy, making cheap flights to Chicago and hotel deals more attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.

  • 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$ 57, while round-trip flights cost around C$ 87.

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

    A round-trip flight to Chicago will typically cost around C$ 222, however they can be found for as little as C$ 72.

  • 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).

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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 4 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

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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.

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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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