CAD/CA
Find cheap flights to Chicago, Illinois in 2026/2027 from C$295 This is the cheapest return flight found to Chicago, Illinois from Canada on FlightsFinder on October 25th 2026 at 06:54. 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.
1. Enter your search requirements for Chicago, Illinois
2. Compare the best Chicago, Illinois deals from top comparison engines
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These economy flights were found on FlightsFinder from Canada to Chicago, Illinois in the last few days. Prices subject to availability.
These economy flights were found on FlightsFinder from Canada to Chicago, Illinois in the last few days. Prices subject to availability.
According to our data, December is on average the cheapest time to book flights to Chicago, Illinois.
You can get flights from C$295 return.
According to our data, September is on average the most expensive time to book flights to Chicago, Illinois.
A return flight could set you back more than C$577.
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.
A good price for a flight to Chicago is C$266 - C$325.
The popular airports near Chicago, Illinois are O'Hare International Airport (ORD), Midway International Airport (MDW), and Chicago Rockford International Airport (RFD).
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).
The best way is to compare flights to Chicago, Illinois from leading comparison sites using our search engine dashboard.
Yes, there are direct flights to 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
The main airport in Chicago, Illinois, O'Hare International Airport, is approximately 17 miles from the city center.
Typically, flights are cheapest to Chicago, Illinois 2 months before departure.
Studies show flights to Chicago, Illinois are typically cheaper on Tuesdays and Wednesdays.
13.9 °C
Mon, 2 Nov 2026
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
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
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 - 61 miles from Mont Tremblant - Montreal / Pierre Elliott Trudeau International Airport (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 - 67 miles from Banff - 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 - 85 miles from Kingston - Ottawa 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)
From Montreal (YUL), Canada to Chicago, United States (ORD): C$297
Depart: 23 Jan 2027 · Return: 23 Jan 2027 Price found 23 Oct 2026, 02:54
From Vancouver (YVR), Canada to Chicago, United States (ORD): C$345
Depart: 09 Dec 2026 · Return: 14 Dec 2026 Price found 26 Oct 2026, 05:49
From Ottawa (YOW), Canada to Chicago, United States (ORD): C$364
Depart: 14 Dec 2026 · Return: 15 Dec 2026 Price found 28 Oct 2026, 01:21
From Calgary (YYC), Canada to Chicago, United States (RFD): C$406
Depart: 07 Jan 2027 · Return: 26 Jan 2027 Price found 25 Oct 2026, 01:41
From Comox (YQQ), Canada to Chicago, United States (ORD): C$473
Depart: 19 Nov 2026 · Return: 26 Nov 2026 Price found 31 Oct 2026, 10:15
From Edmonton (YEG), Canada to Chicago, United States (ORD): C$491
Depart: 09 Dec 2026 · Return: 12 Dec 2026 Price found 30 Oct 2026, 12:18
From Regina (YQR), Canada to Chicago, United States (ORD): C$503
Depart: 25 Dec 2026 · Return: 01 Jan 2027 Price found 29 Oct 2026, 19:13
From Kelowna (YLW), Canada to Chicago, United States (ORD): C$507
Depart: 12 Jan 2027 · Return: 26 Jan 2027 Price found 01 Nov 2026, 09:06
From Winnipeg (YWG), Canada to Chicago, United States (ORD): C$508
Depart: 08 Dec 2026 · Return: 11 Dec 2026 Price found 31 Oct 2026, 02:31
From Halifax (YHZ), Canada to Chicago, United States (ORD): C$524
Depart: 23 Nov 2026 · Return: 01 Dec 2026 Price found 24 Oct 2026, 18:06
From Fort Mcmurray (YMM), Canada to Chicago, United States (ORD): C$537
Depart: 02 Dec 2026 · Return: 07 Dec 2026 Price found 31 Oct 2026, 06:28
From Victoria (YYJ), Canada to Chicago, United States (ORD): C$546
Depart: 09 Dec 2026 · Return: 15 Dec 2026 Price found 24 Oct 2026, 16:50
From Saskatoon (YXE), Canada to Chicago, United States (ORD): C$572
Depart: 28 Jan 2027 · Return: 29 Jan 2027 Price found 23 Oct 2026, 20:36
From Thunder Bay (YQT), Canada to Chicago, United States (ORD): C$591
Depart: 07 Jan 2027 · Return: 10 Feb 2027 Price found 25 Oct 2026, 03:24
From Quebec (YQB), Canada to Chicago, United States (ORD): C$604
Depart: 26 Nov 2026 · Return: 29 Nov 2026 Price found 27 Oct 2026, 09:10
From St John's (YYT), Canada to Chicago, United States (ORD): C$774
Depart: 17 Jan 2027 · Return: 21 Jan 2027 Price found 25 Oct 2026, 09:54
From Moncton (YQM), Canada to Chicago, United States (ORD): C$810
Depart: 24 Jan 2027 · Return: 27 Jan 2027 Price found 28 Oct 2026, 14:00
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