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Flights to Chicago, Illinois

Find cheap flights to Chicago, Illinois in 2024/2025 from C$252 This is the cheapest return flight found to Chicago, Illinois from Canada on FlightsFinder on July 24th 2024 at 15:58. This offer may no longer be available. Click the offer to check live prices & dates of travel.

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Our Flight Finder compares the cheapest flights to Chicago, Illinois from the most established flight comparison sites.
Fly to Chicago, Illinois and visit sites like Willis Tower, Navy Pier, Millennium Park & Cloud Gate.

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2. Compare the best Chicago, Illinois deals from top comparison engines

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What are the cheapest return flights to Chicago, Illinois in 2024/2025?

These economy flights were found on FlightsFinder from Canada to Chicago, Illinois in the last few days. Prices subject to availability.

What are the cheapest one-way flights to Chicago, Illinois in 2024/2025?

These economy flights were found on FlightsFinder from Canada to Chicago, Illinois in the last few days. Prices subject to availability.

When are flights to Chicago, Illinois cheapest?

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The month of October

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According to our data, October is on average the cheapest time to book flights to Chicago, Illinois.
You can get flights from C$252 return.

When is the most expensive time to fly to Chicago, Illinois?

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The month of June

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According to our data, June is on average the most expensive time to book flights to Chicago, Illinois.
A return flight could set you back more than C$597.

Why fly to Chicago, Illinois?

Chicago, Illinois, fondly known as the "Windy City," is a vibrant metropolis that seamlessly blends tradition with innovation. From its iconic architecture showcasing the birthplace of the skyscraper to its rich cultural scene encompassing world-class museums, theaters, and music venues, Chicago offers a dynamic urban experience like no other. The city's diverse neighborhoods each have their own distinct character, from the historic charm of the Loop to the trendy vibes of Wicker Park. Renowned for its deep-dish pizza, passionate sports fans, and stunning waterfront views along Lake Michigan, Chicago invites visitors to explore its unique blend of history, culture, and modernity.

Frequently asked questions about Flights to Chicago, Illinois

What is considered a good price to Chicago, Illinois?

A good price for a flight to Chicago is C$227 - C$277.

Which popular airports are close to Chicago, Illinois?

The popular airports near Chicago, Illinois are O'Hare International Airport (ORD), Midway International Airport (MDW), and Chicago Rockford International Airport (RFD).

How long does it take to fly to Chicago, Illinois?

The flight to Chicago, Illinois (CHI) is roughly 1 hour 28 minutes and 435 miles (701 kilometres) from Toronto, Canada - Airport Lester B. Pearson International (YYZ).

How do I find the cheapest possible flights to Chicago, Illinois?

The best way is to compare flights to Chicago, Illinois from leading comparison sites using our search engine dashboard.

Are there direct flights to Chicago, Illinois?

Yes, there are direct flights to Chicago, Illinois.

What is the weather like in Chicago, Illinois?

Here is the average weather forecast in Chicago, Illinois by month:

• Jan: -0°C
• Feb: 2°C
• Mar: 8°C
• Apr: 15°C
• May: 21°C
• Jun: 27°C
• Jul: 29°C
• Aug: 28°C
• Sep: 24°C
• Oct: 17°C
• Nov: 9°C
• Dec: 2°C

How far is the main airport in Chicago, Illinois from the city centre?

The main airport in Chicago, Illinois, O'Hare International Airport, is approximately 17 miles from the city center.

How far in advance should I book my flight to Chicago, Illinois?

Typically, flights are cheapest to Chicago, Illinois 2 months before departure.

Which day is cheapest to fly to Chicago, Illinois?

Studies show flights to Chicago, Illinois are typically cheaper on Tuesdays and Wednesdays.

Weather in Chicago, Illinois

Clear
Clear

24.5 °C

Sat, 27 Jul 2024

Average Temperature

-0°C

Jan

2°C

Feb

8°C

Mar

15°C

Apr

21°C

May

27°C

Jun

29°C

Jul

28°C

Aug

24°C

Sep

17°C

Oct

9°C

Nov

2°C

Dec

Chicago, Illinois

Famously referred to the world over as the windy city, this metropolis lies adjacent to lake Michigan and is a vibrant and popular place.

Originally named the windy city after a commentary once made about it, the actual origin of the term is largely unknown and most believe it acquired its name because of the severe gales which swoop in from the surrounding lake.

Also sometimes refferred to as the 'second city' this land is one of the most populated in the whole of the United States of America. This is the reason it has acquired that name, as it was widely known as the second most populous area after New York.

Another explanation is that it was named the second city after it was rebuilt after the great fire of Chicago destroyed the entire location forcing the people to rebuild the entire area. This is conjectural however and the majority of people prefer the explanation given above.

The most popular tourist attraction in the city is Sears tower.

The amazing city of Chicago has practically something for every type of person – Whether you are into designer shopping, museums, cheap and cheerful unique neighbourhoods, art galleries or historical places of interest, Chicago will not disappoint.

Right adjacent to the lakefront, stretching from Oak Street Beach to the Gold Coast , the city is brimming with activities for one to do. Moreover there are numerous amusement parks, live concerts and riverboat casinos to select from.

It is near impossible to typecaste the people of this city. Whilst before it was infamous as a gangsters haven today it is home to first class theatres, amazing architecture and it is widely known for their abundance of sports enthusiasts.

Chicago has changed quite drastically over the last 50 or so years. Known nowadays as simply one of the finest cities of America, 3 million residents are know settled in what is now mostly known for the art and culture prevalent in the city.

Not fit to be known as the second city anymore, it is a popular place to hold opening events of major cultural occasions.

So what are you waiting for? find your cheap flights to Chicago now!

Happy Searching!

Cheap Flights Finder - Chicago Flights

Flight Distance and Flying Time to Chicago, Illinois

Toronto, Canada - Airport Lester B. Pearson International (YYZ) to Chicago, Illinois (CHI)

Distance:
435 miles (701 kilometres)

Average flight time (direct 1 hour 28 minutes)

Montreal, Canada - International Airport Pierre E.Trudeau (YUL) to Chicago, Illinois (CHI)

Distance:
746 miles (1,201 kilometres)

Average flight time (direct 2 hours 9 minutes)

Vancouver, Canada - British Columbia, Vancouver International Airport (YVR) to Chicago, Illinois (CHI)

Distance:
1,759 miles (2,831 kilometres)

Average flight time (direct 4 hours 24 minutes)

Calgary, Canada - Calgary International Airport (YYC) to Chicago, Illinois (CHI)

Distance:
1,382 miles (2,224 kilometres)

Average flight time (direct 3 hours 34 minutes)

Edmonton, Canada - Edmonton International Airport (YEG) to Chicago, Illinois (CHI)

Distance:
1,417 miles (2,280 kilometres)

Average flight time (direct 3 hours 38 minutes)

Halifax, Canada - Metropolitan Area Airport (YHZ) to Chicago, Illinois (CHI)

Distance:
1,236 miles (1,989 kilometres)

Average flight time (direct 3 hours 14 minutes)

Ottawa, Canada - Macdonald-Cartier International Airport (YOW) to Chicago, Illinois (CHI)

Distance:
653 miles (1,051 kilometres)

Average flight time (direct 1 hour 57 minutes)

Quebec, Canada - Québec City Jean Lesage International Airport (YQB) to Chicago, Illinois (CHI)

Distance:
879 miles (1,414 kilometres)

Average flight time (direct 2 hours 27 minutes)

Yellowknife, Canada - Yellowknife Airport (YZF) to Chicago, Illinois (CHI)

Distance:
1,781 miles (2,866 kilometres)

Average flight time (direct 4 hours 27 minutes)

Winnipeg, Canada - J.A. Richardson International Airport (YWG) to Chicago, Illinois (CHI)

Distance:
707 miles (1,138 kilometres)

Average flight time (direct 2 hours 4 minutes)

St John's, Canada - St Johns International Airport (YYT) to Chicago, Illinois (CHI)

Distance:
1,751 miles (2,818 kilometres)

Average flight time (direct 4 hours 23 minutes)

Kelowna, Canada - Kelowna International Airport (YLW) to Chicago, Illinois (CHI)

Distance:
1,595 miles (2,566 kilometres)

Average flight time (direct 4 hours 2 minutes)

Sept-Iles, Canada - Sept-Iles Airport (YZV) to Chicago, Illinois (CHI)

Distance:
1,177 miles (1,894 kilometres)

Average flight time (direct 3 hours 6 minutes)

Moncton, Canada - Greater Moncton International Airport (YQM) to Chicago, Illinois (CHI)

Distance:
1,184 miles (1,905 kilometres)

Average flight time (direct 3 hours 7 minutes)

Thunder Bay, Canada - Thunder Bay International Airport (YQT) to Chicago, Illinois (CHI)

Distance:
447 miles (720 kilometres)

Average flight time (direct 1 hour 29 minutes)

Wabush, Canada - Wabush Airport (YWK) to Chicago, Illinois (CHI)

Distance:
1,233 miles (1,984 kilometres)

Average flight time (direct 3 hours 14 minutes)

Victoria Airport, Canada - Victoria International Airport (YYJ) to Chicago, Illinois (CHI)

Distance:
1,769 miles (2,847 kilometres)

Average flight time (direct 4 hours 25 minutes)

Fort McMurray, Canada - Fort McMurray Airport (YMM) to Chicago, Illinois (CHI)

Distance:
1,446 miles (2,328 kilometres)

Average flight time (direct 3 hours 42 minutes)

Comox, Canada - Comox Airport (YQQ) to Chicago, Illinois (CHI)

Distance:
1,838 miles (2,957 kilometres)

Average flight time (direct 4 hours 35 minutes)

Regina, Canada - Regina International Airport (YQR) to Chicago, Illinois (CHI)

Distance:
988 miles (1,590 kilometres)

Average flight time (direct 2 hours 41 minutes)

Timmins, Canada - Victor M. Power Airport (YTS) to Chicago, Illinois (CHI)

Distance:
555 miles (893 kilometres)

Average flight time (direct 1 hour 43 minutes)

Saskatoon, Canada - J.G. Diefenbaker Intl Airport (YXE) to Chicago, Illinois (CHI)

Distance:
1,125 miles (1,810 kilometres)

Average flight time (direct 2 hours 59 minutes)

Map of Chicago, Illinois

Travel Videos About Chicago, Illinois

Cheapest flight routes found to Chicago, Illinois

From Vancouver

From Vancouver (YVR), Canada to Chicago, United States (MDW): C$252

Depart: 22 Oct 2024 · Return: 26 Oct 2024 Price found 24 Jul 2024, 15:58

From Calgary

From Calgary (YYC), Canada to Chicago, United States (ORD): C$263

Depart: 28 Sep 2024 · Return: 06 Oct 2024 Price found 26 Jul 2024, 14:56

From Edmonton

From Edmonton (YEG), Canada to Chicago, United States (MDW): C$269

Depart: 09 Oct 2024 · Return: 23 Oct 2024 Price found 26 Jul 2024, 09:23

From Montreal

From Montreal (YUL), Canada to Chicago, United States (MDW): C$283

Depart: 01 Sep 2024 · Return: 11 Sep 2024 Price found 26 Jul 2024, 07:11

From Winnipeg

From Winnipeg (YWG), Canada to Chicago, United States (ORD): C$285

Depart: 06 Sep 2024 · Return: 08 Sep 2024 Price found 24 Jul 2024, 10:33

From Halifax

From Halifax (YHZ), Canada to Chicago, United States (MDW): C$317

Depart: 28 Aug 2024 · Return: 04 Sep 2024 Price found 26 Jul 2024, 05:56

From Regina

From Regina (YQR), Canada to Chicago, United States (ORD): C$341

Depart: 21 Sep 2024 · Return: 22 Sep 2024 Price found 25 Jul 2024, 19:17

From Kelowna

From Kelowna (YLW), Canada to Chicago, United States (ORD): C$376

Depart: 11 Sep 2024 · Return: 18 Sep 2024 Price found 27 Jul 2024, 03:27

From Victoria

From Victoria (YYJ), Canada to Chicago, United States (ORD): C$394

Depart: 07 Sep 2024 · Return: 09 Sep 2024 Price found 26 Jul 2024, 03:43

From Thunder Bay

From Thunder Bay (YQT), Canada to Chicago, United States (MDW): C$405

Depart: 17 Oct 2024 · Return: 21 Oct 2024 Price found 26 Jul 2024, 17:11

From Quebec

From Quebec (YQB), Canada to Chicago, United States (MDW): C$420

Depart: 03 Sep 2024 · Return: 06 Sep 2024 Price found 24 Jul 2024, 23:50

From Saskatoon

From Saskatoon (YXE), Canada to Chicago, United States (ORD): C$429

Depart: 03 Sep 2024 · Return: 06 Sep 2024 Price found 25 Jul 2024, 23:39

From Ottawa

From Ottawa (YOW), Canada to Chicago, United States (ORD): C$435

Depart: 06 Sep 2024 · Return: 10 Sep 2024 Price found 24 Jul 2024, 22:06

From Moncton

From Moncton (YQM), Canada to Chicago, United States (MDW): C$488

Depart: 12 Sep 2024 · Return: 16 Sep 2024 Price found 26 Jul 2024, 13:19

From Comox

From Comox (YQQ), Canada to Chicago, United States (MDW): C$537

Depart: 21 Sep 2024 · Return: 24 Sep 2024 Price found 25 Jul 2024, 00:26

From St John's

From St John's (YYT), Canada to Chicago, United States (ORD): C$551

Depart: 22 Oct 2024 · Return: 29 Oct 2024 Price found 25 Jul 2024, 15:41

From Fort Mcmurray

From Fort Mcmurray (YMM), Canada to Chicago, United States (MDW): C$774

Depart: 10 Dec 2024 · Return: 24 Jan 2025 Price found 23 Jul 2024, 14:23

From Timmins

From Timmins (YTS), Canada to Chicago, United States (ORD): C$781

Depart: 16 Nov 2024 · Return: 18 Nov 2024 Price found 25 Jul 2024, 14:29

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