How popular are flights to Chicago this year?

Chicago flights are currently seeing a 102% increase in searches when contrasted with this time last year.

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.

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 does offer price alerts on Chicago flights so you can book your travels when it’s right. The Price Alert feature is available after a flight search is performed above.

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$ 203

Q: 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.

Flights to Chicago in 2023

Popular in	March
Cheapest in	June
Average price	C$ 326
Round-trip from	C$ 352
One-way from	C$ 203

High demand for flights, 7% 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 May 2023

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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 May, June 2023

The below flights offer some of the lowest fares to Chicago in May and June 2023. Be sure to check back soon as deals update often.

20 Jun. - 22 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 352

Porter Airlines

Deal found 30/5

20 Jun. - 22 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 355

Porter Airlines

Deal found 29/5

29 Jun. - 3 Jul.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 367

Porter Airlines

Deal found 30/5

21 Jun. - 21 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 374

Porter Airlines

Deal found 30/5

17 Jun. - 20 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 378

Porter Airlines

Deal found 30/5

29 Jun. - 3 Jul.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 379

Porter Airlines

Deal found 30/5

29 Jun. - 3 Jul.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 381

Porter Airlines

Deal found 30/5

17 Jun. - 20 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 382

Porter Airlines

Deal found 29/5

24 Jun. - 27 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 387

Porter Airlines

Deal found 30/5

Chicago 2023 flight deals

Listed are some of the best fares we've found on flights departing to Chicago in 2023. If these deals don't appeal to you, be sure to come back soon for more options.

20 Jun. - 22 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 352

Porter Airlines

Deal found 30/5

20 Jun. - 22 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 355

Porter Airlines

Deal found 29/5

29 Jun. - 3 Jul.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 367

Porter Airlines

Deal found 30/5

10 Nov. - 15 Nov.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 01m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 30m

C$ 371

American Airlines

Deal found 29/5

21 Jun. - 21 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 374

Porter Airlines

Deal found 30/5

17 Jun. - 20 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 378

Porter Airlines

Deal found 30/5

29 Jun. - 3 Jul.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 379

Porter Airlines

Deal found 30/5

29 Jun. - 3 Jul.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m

C$ 381

Porter Airlines

Deal found 30/5

10 Nov. - 15 Nov.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 01m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

7h 30m

C$ 382

American Airlines

Deal found 29/5

Last minute flights to Chicago

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

7 Jun. - 14 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

9h 46m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

2 stops

24h 30m

C$ 480

Multiple Airlines

Deal found 29/5

7 Jun. - 14 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

9h 46m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

3 stops

28h 25m

C$ 488

Multiple Airlines

Deal found 29/5

5 Jun. - 7 Jun.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

2 stops

34h 28m

MDW

Chicago Midway

YYZ

Toronto Pearson Intl

2 stops

29h 30m

C$ 488

Multiple Airlines

Deal found 30/5

6 Jun. - 13 Jun.

YHM

Hamilton

ORD

Chicago O'Hare Intl

1 stop

9h 56m

ORD

Chicago O'Hare Intl

YHM

Hamilton

1 stop

7h 42m

C$ 517

Multiple Airlines

Deal found 30/5

10 Jun. - 13 Jun.

YHM

Hamilton

ORD

Chicago O'Hare Intl

1 stop

10h 05m

ORD

Chicago O'Hare Intl

YHM

Hamilton

1 stop

7h 42m

C$ 518

Multiple Airlines

Deal found 30/5

10 Jun. - 13 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

11h 35m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

2 stops

20h 07m

C$ 530

Multiple Airlines

Deal found 30/5

10 Jun. - 14 Jun.

YHM

Hamilton

ORD

Chicago O'Hare Intl

1 stop

12h 41m

ORD

Chicago O'Hare Intl

YHM

Hamilton

1 stop

14h 43m

C$ 530

Multiple Airlines

Deal found 30/5

5 Jun. - 8 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

9h 22m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

8h 32m

C$ 533

Multiple Airlines

Deal found 30/5

8 Jun. - 11 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

8h 15m

ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

20h 50m

C$ 538

Multiple Airlines

Deal found 29/5

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.

28 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

C$ 203

Porter Airlines

Deal found 31/5

13 Jun.

YHM

Hamilton

ORD

Chicago O'Hare Intl

2 stops

26h 42m

C$ 209

Multiple Airlines

Deal found 30/5

20 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

C$ 215

Porter Airlines

Deal found 30/5

13 Sep.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 57m

C$ 216

American Airlines

Deal found 30/5

13 Sep.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 57m

C$ 217

American Airlines

Deal found 31/5

28 Jun.

YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m

C$ 217

Porter Airlines

Deal found 30/5

30 Aug.

YYZ

Toronto Pearson Intl

MDW

Chicago Midway

2 stops

15h 23m

C$ 220

Multiple Airlines

Deal found 30/5

21 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m

C$ 222

Air Canada

Deal found 30/5

20 Jun.

YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 55m

C$ 227

Air Canada

Deal found 30/5

Find flights to Chicago within your budget

Fly from

Budget

C$ 352 - C$ 555

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Tue 20/6

Nonstop1h 47m

Chicago Midway

Thu 22/6

Nonstop1h 42m

C$ 352

Pick Dates

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Tue 20/6

Nonstop1h 47m

Chicago Midway

Thu 22/6

Nonstop1h 42m

C$ 355

Pick Dates

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/11

Nonstop2h 01m

Chicago O'Hare Intl

Wed 15/11

Nonstop1h 30m

C$ 371

Pick Dates

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/11

Nonstop2h 01m

Chicago O'Hare Intl

Wed 15/11

1 stop7h 30m

C$ 382

Pick Dates

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 30/8

1 stop9h 04m

Chicago O'Hare Intl

Wed 6/9

1 stop9h 49m

C$ 402

Pick Dates

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 21/6

1 stop9h 35m

Chicago O'Hare Intl

Mon 26/6

1 stop10h 55m

C$ 408

Pick Dates

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 21/6

Nonstop1h 55m

Chicago O'Hare Intl

Fri 23/6

Nonstop1h 43m

C$ 432

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 1/8

1 stop12h 24m

Chicago Midway

Tue 8/8

1 stop15h 19m

C$ 526

Pick Dates

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 27/7

1 stop7h 40m

Chicago Midway

Tue 8/8

1 stop8h 05m

C$ 555

Pick Dates

Flights are sorted by cheapest first

Deals found on 30/5

What is the cheapest month to fly to Chicago?

January

C$ 396

February

C$ 431

March

C$ 477

April

C$ 477

May

C$ 416

June

C$ 449

July

C$ 438

August

C$ 499

September

C$ 438

October

C$ 396

November

C$ 397

December

C$ 401

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.

When is the best time to fly to Chicago?

YTO - CHI Price	C$ 350 - C$ 494
CHI Temperature	-5 - 23 °C
CHI Rainfall	43 - 125 mm

YTO - CHI

Price

C$ 350 - C$ 494

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

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 59 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

Which day is cheapest to fly to Chicago?

The cheapest day to fly to Chicago is usually Thursday. At the moment, Sunday is the most expensive.

Search Deals

What time of day is cheapest to fly to Chicago?

Flights at noon are typically the cheapest time of the day to fly to Chicago. Flights in the morning are usually the most expensive.

Search Deals

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.

Toronto Island to Midway flightsfrom C$ 354 pp

Pearson Intl to O'Hare Intl flightsfrom C$ 454 pp

Ottawa to O'Hare Intl flightsfrom C$ 478 pp

Calgary to O'Hare Intl flightsfrom C$ 546 pp

Québec City to O'Hare Intl flightsfrom C$ 565 pp

Other local departures to Chicago from Canada

Chicago, Illinois airports

Flights to Midway

Flights to O'Hare Intl

Pearson Intl to Fort Lauderdale flightsfrom C$ 154 pp

Calgary to Los Angeles flightsfrom C$ 173 pp

Pearson Intl to Orlando flightsfrom C$ 208 pp

Pearson Intl to Las Vegas flightsfrom C$ 220 pp

Toronto Island to Newark flightsfrom C$ 229 pp

Pearson Intl to John F Kennedy Intl flightsfrom C$ 261 pp

Pearson Intl to LaGuardia flightsfrom C$ 262 pp

Ottawa to Newark flightsfrom C$ 275 pp

Pearson Intl to Newark flightsfrom C$ 323 pp

Pearson Intl to Los Angeles flightsfrom C$ 343 pp

Pearson Intl to Miami flightsfrom C$ 346 pp

Pearson Intl to Atlanta flightsfrom C$ 376 pp

Pearson Intl to Detroit flightsfrom C$ 392 pp

Pearson Intl to Dulles Intl flightsfrom C$ 394 pp

Pearson Intl to O'Hare Intl flightsfrom C$ 454 pp

Pearson Intl to San Francisco flightsfrom C$ 537 pp

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Search flights to Chicago by cabin class

First Classfrom C$ 1,179/person

Business Classfrom C$ 562/person

Prem Economyfrom C$ 503/person

Economyfrom C$ 179/person

Fly your favourite airline to Chicago

Air Canada flights from Pearson Intl to O'Hare Intl

American Airlines flights from Pearson Intl to O'Hare Intl

Cheap flights to Chicago

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Flights to Chicago in 2023

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.

Popular in

Cheapest in

Average price

Round-trip from

One-way from

Cheap flights to Chicago in May, June 2023

The best prices found for CHI flights for May, June

The below flights offer some of the lowest fares to Chicago in May and June 2023. Be sure to check back soon as deals update often.

Chicago 2023 flight deals

Cheap flights to Chicago found for this year

Listed are some of the best fares we've found on flights departing to Chicago in 2023. If these deals don't appeal to you, be sure to come back soon for more options.

Last minute flights to Chicago

Late deals on round-trip flights to Chicago, departing today and this week

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

The cheapest 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.

Find flights to Chicago within your budget

Use the slider to find flights to Chicago that fit your budget.

What is the cheapest month to fly to Chicago?

The cheapest ticket to Chicago found for each month in 2023 based on historical flight searches by Cheapflights users.

When is the best time to fly to Chicago?

Average Chicago flight ticket prices and weather conditions for 2023 and 2024 by month

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 59 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.

Which day is cheapest to fly to Chicago?

The cheapest day to fly to Chicago is usually Thursday. At the moment, Sunday is the most expensive.

What time of day is cheapest to fly to Chicago?

Flights at noon are typically the cheapest time of the day to fly to Chicago. Flights in the morning are usually the most expensive.

When is the best time to fly?

What is good to know if travelling to Chicago?

How popular are flights to Chicago this year?

What does ORD mean?

Find the best Chicago flight deals for you

Cheap tickets to Chicago found by our users in Canada as recently as 31 May 2023.

Other local departures to Chicago from Canada

Chicago, Illinois airports

See all airports in Chicago, select one to find and compare flight prices.

Cheapest flights to the United States

Not set on Chicago? See the cheapest flights to the United States. Airfare prices updated on 31 May 2023.

Popular flight searches

Check out other popular destinations found by fellow travellers in 2023

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