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Flights to Chicago, Illinois

Find cheap flights to Chicago, Illinois in 2025/2026 from C$219 This is the cheapest return flight found to Chicago, Illinois from Canada on FlightsFinder on March 24th 2025 at 14:46. 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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What are the cheapest return flights to Chicago, Illinois in 2025/2026?

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 2025/2026?

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 May

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According to our data, May is on average the cheapest time to book flights to Chicago, Illinois.
You can get flights from C$219 return.

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

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The month of February

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According to our data, February is on average the most expensive time to book flights to Chicago, Illinois.
A return flight could set you back more than C$426.

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

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What is the weather like in Chicago, Illinois?

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Which day is cheapest to fly to Chicago, Illinois?

Weather in Chicago, Illinois

Clouds
Clouds

1.5 °C

Tue, 25 Mar 2025

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 Calgary

From Calgary (YYC), Canada to Chicago, United States (ORD): C$219

Depart: 11 May 2025 · Return: 13 May 2025 Price found 24 Mar 2025, 14:46

From Edmonton

From Edmonton (YEG), Canada to Chicago, United States (ORD): C$250

Depart: 14 Sep 2025 · Return: 27 Sep 2025 Price found 23 Mar 2025, 13:51

From Montreal

From Montreal (YUL), Canada to Chicago, United States (MDW): C$281

Depart: 19 Apr 2025 · Return: 24 Apr 2025 Price found 24 Mar 2025, 01:43

From Vancouver

From Vancouver (YVR), Canada to Chicago, United States (ORD): C$289

Depart: 12 May 2025 · Return: 13 May 2025 Price found 24 Mar 2025, 14:49

From Saskatoon

From Saskatoon (YXE), Canada to Chicago, United States (ORD): C$308

Depart: 02 Jun 2025 · Return: 09 Jun 2025 Price found 22 Mar 2025, 18:40

From Kelowna

From Kelowna (YLW), Canada to Chicago, United States (ORD): C$323

Depart: 13 May 2025 · Return: 16 May 2025 Price found 21 Mar 2025, 16:06

From Victoria

From Victoria (YYJ), Canada to Chicago, United States (ORD): C$326

Depart: 02 May 2025 · Return: 11 May 2025 Price found 24 Mar 2025, 15:39

From Regina

From Regina (YQR), Canada to Chicago, United States (ORD): C$330

Depart: 09 May 2025 · Return: 13 May 2025 Price found 22 Mar 2025, 05:50

From Winnipeg

From Winnipeg (YWG), Canada to Chicago, United States (ORD): C$349

Depart: 10 May 2025 · Return: 14 May 2025 Price found 23 Mar 2025, 07:48

From Ottawa

From Ottawa (YOW), Canada to Chicago, United States (MDW): C$363

Depart: 02 May 2025 · Return: 06 May 2025 Price found 22 Mar 2025, 09:55

From Halifax

From Halifax (YHZ), Canada to Chicago, United States (MDW): C$379

Depart: 10 Jun 2025 · Return: 24 Jun 2025 Price found 21 Mar 2025, 21:42

From Thunder Bay

From Thunder Bay (YQT), Canada to Chicago, United States (MDW): C$437

Depart: 14 Apr 2025 · Return: 23 Apr 2025 Price found 22 Mar 2025, 20:59

From Comox

From Comox (YQQ), Canada to Chicago, United States (ORD): C$440

Depart: 05 May 2025 · Return: 12 May 2025 Price found 21 Mar 2025, 21:22

From Timmins

From Timmins (YTS), Canada to Chicago, United States (MDW): C$573

Depart: 02 Apr 2025 · Return: 12 Apr 2025 Price found 23 Mar 2025, 05:09

From Quebec

From Quebec (YQB), Canada to Chicago, United States (ORD): C$574

Depart: 05 May 2025 · Return: 08 May 2025 Price found 23 Mar 2025, 00:37

From Fort Mcmurray

From Fort Mcmurray (YMM), Canada to Chicago, United States (ORD): C$584

Depart: 21 Apr 2025 · Return: 13 May 2025 Price found 23 Mar 2025, 02:56

From Moncton

From Moncton (YQM), Canada to Chicago, United States (ORD): C$632

Depart: 30 May 2025 · Return: 06 Jun 2025 Price found 21 Mar 2025, 13:10

From St John's

From St John's (YYT), Canada to Chicago, United States (ORD): C$734

Depart: 30 Jul 2025 · Return: 03 Aug 2025 Price found 24 Mar 2025, 19:27