What is the cheapest month to fly to Chicago?

Currently, January is the cheapest month in which you can book a flight to Chicago . Flying to Chicago in August will prove the most costly. There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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.

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, Porter Airlines 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 Airport is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl Airport typically cost C$ 33, while round-trip flights cost around C$ 70.

How much is a round-trip flight to Chicago?

A round-trip flight to Chicago will typically cost around C$ 144, however they can be found for as little as C$ 51.

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 47 minutes).

Does Chicago O'Hare Intl Airport have rental cars?

Yes. Those touching down at Chicago O'Hare Intl Airport can take advantage of the rental car services offered upon their arrival.

Are there hotels close to Chicago O'Hare Intl Airport?

Yes. Chicago O'Hare Intl Airport has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl Airport (0.0 km away from Chicago O'Hare Intl Airport).

ORD stands for Chicago O'Hare Intl Airport. Codes like this one are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight destination and their unique identifiers/IATA codes.

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.

Cheap Flights to Chicago from C$ 150

Flights to Chicago in 2024

Popular in	July
Cheapest in	January
Average price	C$ 353
Round-trip from	C$ 305
One-way from	C$ 150

High demand for flights, 13% potential price rise

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Best time to find cheap flights, 1% potential price drop

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Average for round-trip flights in April 2024

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From Toronto to Chicago

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One-way flight from Toronto to Chicago

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Cheap flights to Chicago in April & May 2024

The below flights offer some of the lowest fares to Chicago in April and May 2024. Be sure to check back soon as deals update often.

Wed 15/56:30 a.m.YYZ - ORD

1 stop11h 05mMultiple Airlines

Thu 16/511:48 a.m.ORD - YYZ

1 stop6h 47mMultiple Airlines

Deal found 25/4C$ 305

Tue 7/56:30 a.m.YYZ - ORD

1 stop12h 16mMultiple Airlines

Tue 14/57:00 a.m.ORD - YYZ

2 stops22h 35mMultiple Airlines

Deal found 26/4C$ 311

Wed 8/56:30 a.m.YYZ - ORD

1 stop11h 05mMultiple Airlines

Tue 14/56:40 p.m.ORD - YYZ

1 stop26h 55mMultiple Airlines

Deal found 25/4C$ 313

Thu 23/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 30/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 313

Thu 23/53:30 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 26/58:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 315

Fri 24/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 27/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 316

Thu 23/53:30 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 30/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 317

Tue 21/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Wed 22/511:05 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 322

Fri 24/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 27/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 326

Chicago 2024 flight deals

Listed are some of the best fares we've found on flights departing to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.

Wed 15/56:30 a.m.YYZ - ORD

1 stop11h 05mMultiple Airlines

Thu 16/511:48 a.m.ORD - YYZ

1 stop6h 47mMultiple Airlines

Deal found 25/4C$ 305

Tue 7/56:30 a.m.YYZ - ORD

1 stop12h 16mMultiple Airlines

Tue 14/57:00 a.m.ORD - YYZ

2 stops22h 35mMultiple Airlines

Deal found 26/4C$ 311

Wed 8/56:30 a.m.YYZ - ORD

1 stop11h 05mMultiple Airlines

Tue 14/56:40 p.m.ORD - YYZ

1 stop26h 55mMultiple Airlines

Deal found 25/4C$ 313

Thu 23/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 30/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 313

Thu 23/53:30 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 26/58:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 315

Fri 24/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 27/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 316

Thu 23/53:30 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 30/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 317

Tue 21/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Wed 22/511:05 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 322

Fri 24/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 27/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 326

Flights to Chicago departing soon

Browse some of the best deals on flights leaving last minute to Chicago. Tip: double check your flight details before making your reservation.

Sat 4/512:35 p.m.YYZ - ORD

1 stop12h 45mMultiple Airlines

Sat 11/56:10 a.m.ORD - YYZ

2 stops11h 45mMultiple Airlines

Deal found 25/4C$ 380

Sun 5/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 12/58:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 384

Sat 4/56:15 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 12/58:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 386

Sat 4/512:35 p.m.YYZ - ORD

1 stop12h 45mMultiple Airlines

Mon 6/54:30 p.m.ORD - YYZ

2 stops26h 05mMultiple Airlines

Deal found 25/4C$ 406

Sun 5/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Fri 10/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 415

Thu 2/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 9/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 416

Sat 4/512:35 p.m.YYZ - ORD

1 stop12h 45mMultiple Airlines

Mon 6/57:45 a.m.ORD - YYZ

3 stops34h 50mMultiple Airlines

Deal found 25/4C$ 432

Fri 3/59:20 a.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Fri 10/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 432

Sun 5/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 13/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 443

One-way flights to Chicago

Take a look at some of the one-way flights departing to Chicago in the near future. Reserve a round-trip flight to Chicago instead by utilizing the search form above.

Tue 7/56:30 a.m.YYZ - ORD

1 stop12h 16mMultiple Airlines

Deal found 25/4C$ 150

Tue 7/56:30 a.m.YYZ - ORD

1 stop12h 16mMultiple Airlines

Deal found 25/4C$ 155

Wed 29/57:45 a.m.YYZ - ORD

1 stop15h 01mMultiple Airlines

Deal found 25/4C$ 167

Tue 7/56:30 a.m.YYZ - ORD

1 stop12h 16mMultiple Airlines

Deal found 24/4C$ 170

Tue 7/56:30 a.m.YYZ - ORD

1 stop18h 50mMultiple Airlines

Deal found 25/4C$ 171

Tue 21/56:30 a.m.YYZ - ORD

1 stop12h 10mMultiple Airlines

Deal found 25/4C$ 175

Tue 7/56:30 a.m.YYZ - ORD

2 stops15h 15mMultiple Airlines

Deal found 25/4C$ 176

Tue 7/56:30 a.m.YYZ - ORD

2 stops15h 15mMultiple Airlines

Deal found 25/4C$ 179

Sat 25/56:30 a.m.YYZ - ORD

1 stop12h 10mMultiple Airlines

Deal found 25/4C$ 183

Direct flights to Chicago

Thu 23/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 30/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 313

Thu 23/53:30 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 26/58:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 315

Fri 24/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 27/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 316

Thu 23/53:30 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Thu 30/55:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 317

Tue 21/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Wed 22/511:05 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 24/4C$ 322

Fri 24/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Mon 27/58:00 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 326

Thu 23/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 26/512:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 327

Thu 23/58:50 p.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 26/58:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 26/4C$ 328

Thu 23/59:20 a.m.YTZ - MDW

Nonstop1h 47mPorter Airlines

Sun 26/512:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 25/4C$ 331

Average price of flights to Chicago by month

Currently, January is the cheapest month in which you can book a flight to Chicago (average of C$ 261). Flying to Chicago in August will prove the most costly (average of C$ 452). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

January

C$ 357

February

C$ 416

March

C$ 443

April

C$ 456

May

C$ 536

June

C$ 561

July

C$ 606

August

C$ 618

September

C$ 473

October

C$ 509

November

C$ 462

December

C$ 478

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.

Temperature and rainfall in Chicago by month

CHI Temperature	-5 - 23 °C

CHI

Temperature

-5 - 23 °C

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).

When is the best time to book a flight to Chicago?

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 78 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.

Search Deals

When is the cheapest time to fly to Chicago?

Morning

Noon

Afternoon

Evening

All times are departure.

Users looking for the lowest fares to Chicago should consider flying on Saturday evenings, 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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Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Air Canada, American Airlines and United Airlines 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

8.1

Very good

10,966 reviews

Check prices

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta

8.1

Very good

10,966 reviews

Delta

8.1

Very good

10,966 reviews

Check prices

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

KLM

7.9

Good

1,626 reviews

Delta

8.1

Very good

10,966 reviews

Check prices

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

WestJet

7.5

Good

2,981 reviews

Delta

8.1

Very good

10,966 reviews

Check prices

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Porter Airlines

7.4

Good

438 reviews

Delta

8.1

Very good

10,966 reviews

Check prices

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

United Airlines

7.4

Good

11,228 reviews

Delta

8.1

Very good

10,966 reviews

Check prices

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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.
What does ORD mean?
ORD stands for Chicago O'Hare Intl Airport. Codes like this one are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight destination and their unique identifiers/IATA codes.
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, Porter Airlines 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 Airport is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl Airport typically cost C$ 33, while round-trip flights cost around C$ 70.
How much is a round-trip flight to Chicago?
A round-trip flight to Chicago will typically cost around C$ 144, however they can be found for as little as C$ 51.
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 47 minutes).
Does Chicago O'Hare Intl Airport have rental cars?
Yes. Those touching down at Chicago O'Hare Intl Airport can take advantage of the rental car services offered upon their arrival.
Are there hotels close to Chicago O'Hare Intl Airport?
Yes. Chicago O'Hare Intl Airport has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl Airport (0.0 km away from Chicago O'Hare Intl Airport).

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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 26 April 2024.

Air Canada flights from Pearson Intl to O'Hare Intl

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Some of the lowest fares we’ve come across for flights from Chicago.

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Search flights to Chicago by cabin class

First Classfrom C$ 445/person

Business Classfrom C$ 411/person

Prem Econ Classfrom C$ 826/person

Economy Classfrom C$ 173/person

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Cheap flights to Chicago from C$ 150

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 7/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.

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 508,915 searches and data was last updated on 26 April 2024.

Popular in

Cheapest in

Average price

Round-trip from

One-way from

Cheap flights to Chicago in April & May 2024

Discover affordable flights and deals to Chicago in April and May 2024. In the last 7 days, Cheapflights users made a total of 508,915 searches and data was last updated on 26 April 2024.

The below flights offer some of the lowest fares to Chicago in April and May 2024. Be sure to check back soon as deals update often.

Chicago 2024 flight deals

Explore flight deals for Chicago in 2024, offering the best prices and options to suit your preferences. In the last 7 days, Cheapflights users made a total of 508,915 searches and data were last updated on 26 April 2024.

Listed are some of the best fares we've found on flights departing to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.

Flights to Chicago departing soon

Discover available last-minute flight options to Chicago, providing immediate availability and potentially lower prices. In the last 7 days, Cheapflights users made a total of 508,915 searches and data was last updated on 26 April 2024.

Browse some of the best deals on flights leaving last minute to Chicago. Tip: double check your flight details before making your reservation.

One-way flights to Chicago

Explore one-way flight options to Chicago for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 508,915 searches and data was last updated on 26 April 2024.

Take a look at some of the one-way flights departing to Chicago in the near future. Reserve a round-trip flight to Chicago instead by utilizing the search form above.

Direct flights to Chicago

Average price of flights to Chicago by month

Plan your trip to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight to Chicago is currently C$ 170 while a round-trip flight costs C$ 385. Price data was last updated on 21 April 2024.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

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 to Chicago. Price data was last updated on 28 January 2024.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 78 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.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip to Chicago. Price data was last updated on 21 April 2024.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Air Canada, American Airlines and United Airlines 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.

What is good to know if travelling to Chicago?

What does ORD mean?

Can I find cheaper flights to Chicago if I am willing to have layovers?

What is the best airline to fly to Chicago?

What is the cheapest airport to fly to in Chicago?

How much is a round-trip flight to Chicago?

Where does the fastest flight to Chicago depart from?

Does Chicago O'Hare Intl Airport have rental cars?

Are there hotels close to Chicago O'Hare Intl Airport?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly your favourite airline to ChicagoFly your favourite airline to Chicago. Flight routes are based on user searches made on Cheapflights and were last updated on 26 April 2024.

Fly your favourite airline to Chicago. Flight routes are based on user searches made on Cheapflights and were last updated on 26 April 2024.

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User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations

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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 26 April 2024.