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.
The cheapest month of the year to fly to Chicago, Illinois is typically January.
The best price we found is for C$254 from Toronto to Chicago.
Some popular airlines include: Flair Airlines, WestJet, United, Sun Country Airlines, Spirit Airlines, Qatar Airways, PAL Airlines, Porter Airlines (Canada) Ltd, Frontier Airlines, Delta, Air Canada.
A good price for a flight to Chicago is C$229 - C$279.
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.
Super-tall skyscraper with city vistas
Destination with rides, shops & food
Green space with art, theater & ice rink
Mirrored, bean-shaped sculpture
Renowned art museum with global works
Sky-high city views from 94th-floor deck
Aquatic creatures from around the world
Panoramic views from 1353 feet above
Home to numerous Downtown attractions
Free zoo with an interactive farm
Posh shops & the John Hancock Center
State-of-the-art science museum
Museum with high-tech exhibits & shows
Cubs’ historic ballpark
Observatory with tilting glass platform
Elaborate rococo landmark from 1927
Scenic walkway along the Chicago River
Free cultural exhibits, concerts & more
Interactive educational museum
Large LED sculpture with reflecting pool
Art gallery inside a historic landmark
Urban design organization
Sprawling zoo with thousands of animals
Hands-on-experiences for kids
Bandshell in the park with entertainment
The famed Prairie-style architect’s home
Thousands of plants under a glass dome
Chicago history brought to life
Gardens, athletic fields, fishing & more
Frank Lloyd Wright-designed landmark
Sandy city beach with lifeguards
Popular summer spot with dining & stores
Busy hangout with playgrounds & skating
Environment-focused kid-friendly museum
Lakefront park with famed institutions
5-acre urban botanical park
Skyscraper with French Gothic elements
Extensive path with water & city views
Restored Gilded Age mansion
Landmark 1920s skyscraper & clock tower
Recreational trail on a former rail line
Food, art & entertainment on a riverwalk
Vast public space with a zoo & museums
Landscaped green space & tennis courts
Chicago River & Lake Michigan tours
Green space with a beach & gardens
Historic tower with notable lobby design
Historic drawbridge with decorative work
Exhibits covering art, culture & history
Middle Eastern art & antiquities
Memorial to social reformer Jane Addams
Art deco tower crowned with Ceres statue
Concert, music venue, and planetarium
Stately mansions & Oak Street Beach
Architecture, ludwig mies van der rohe, marina, and modern architecture
Landmark 19th century house museum
Winding footbridge by architect Gehry
Monument, history, park, and architecture
Venue for home showrooms & trade shows
Park with ice skating & a restaurant
1953 temple with intricate facade
Tourist attraction
50-ft. steel sculpture by iconic artist
Architecture
Modern architecture and architecture
Dedicated to the history of surgery
Rotating shows plus events & programs
Frank lloyd wright and architecture
Arboretum & renowned burial place
Cruise line company
Architecture
Tranquil space with a pond & vegetation
Swimming spot with city skyline views
Museum
Mexican & Mexican-American artworks
Beach and kitesurfing
Wizard of Oz-themed playground & park
Hop-on/hop-off city highlights tours
Point of interest
Park and architecture
River views, kayak rentals & playground
Seasonal swimming beach with amenities
Museum and literature
Picnic spot on a man-made peninsula
Art & design, from ancient to modern
Gambling, dining & entertainment
Monument
Office block, once the world's largest
Chicago's oldest surviving home
Ice skating
Specialty dolls with historic relevance
Home to the Chicago Symphony Orchestra
Nature preserve & educational center
Observation deck
Cathedral, gothic architecture, and architecture
Ludwig mies van der rohe, wassily kandinsky, modern architecture, and architecture
Large research collection & rare books
Monumental 1974 abstract sculpture
Cycling, trail running, river, running, and hiking
13.6 °C
Fri, 26 Apr 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
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
Flights from Toronto, Canada - Airport Lester B. Pearson International (YYZ) to Chicago, Illinois (CHI) - The flight distance between these airports is 435 miles (701 kilometres). The direct flight time is roughly 1 hour 28 minutes.
Flights from Montreal, Canada - International Airport Pierre E.Trudeau (YUL) to Chicago, Illinois (CHI) - The flight distance between these airports is 746 miles (1,201 kilometres). The direct flight time is roughly 2 hours 9 minutes.
Flights from Vancouver, Canada - British Columbia, Vancouver International Airport (YVR) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,759 miles (2,831 kilometres). The direct flight time is roughly 4 hours 24 minutes.
Flights from Calgary, Canada - Calgary International Airport (YYC) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,382 miles (2,224 kilometres). The direct flight time is roughly 3 hours 34 minutes.
Flights from Edmonton, Canada - Edmonton International Airport (YEG) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,417 miles (2,280 kilometres). The direct flight time is roughly 3 hours 38 minutes.
Flights from Halifax, Canada - Metropolitan Area Airport (YHZ) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,236 miles (1,989 kilometres). The direct flight time is roughly 3 hours 14 minutes.
Flights from Ottawa, Canada - Macdonald-Cartier International Airport (YOW) to Chicago, Illinois (CHI) - The flight distance between these airports is 653 miles (1,051 kilometres). The direct flight time is roughly 1 hour 57 minutes.
Flights from Quebec, Canada - Québec City Jean Lesage International Airport (YQB) to Chicago, Illinois (CHI) - The flight distance between these airports is 879 miles (1,414 kilometres). The direct flight time is roughly 2 hours 27 minutes.
Flights from Yellowknife, Canada - Yellowknife Airport (YZF) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,781 miles (2,866 kilometres). The direct flight time is roughly 4 hours 27 minutes.
Flights from Winnipeg, Canada - J.A. Richardson International Airport (YWG) to Chicago, Illinois (CHI) - The flight distance between these airports is 707 miles (1,138 kilometres). The direct flight time is roughly 2 hours 4 minutes.
Flights from St John's, Canada - St Johns International Airport (YYT) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,751 miles (2,818 kilometres). The direct flight time is roughly 4 hours 23 minutes.
Flights from Kelowna, Canada - Kelowna International Airport (YLW) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,595 miles (2,566 kilometres). The direct flight time is roughly 4 hours 2 minutes.
Flights from Sept-Iles, Canada - Sept-Iles Airport (YZV) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,177 miles (1,894 kilometres). The direct flight time is roughly 3 hours 6 minutes.
Flights from Moncton, Canada - Greater Moncton International Airport (YQM) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,184 miles (1,905 kilometres). The direct flight time is roughly 3 hours 7 minutes.
Flights from Thunder Bay, Canada - Thunder Bay International Airport (YQT) to Chicago, Illinois (CHI) - The flight distance between these airports is 447 miles (720 kilometres). The direct flight time is roughly 1 hour 29 minutes.
Flights from Wabush, Canada - Wabush Airport (YWK) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,233 miles (1,984 kilometres). The direct flight time is roughly 3 hours 14 minutes.
Flights from Victoria Airport, Canada - Victoria International Airport (YYJ) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,769 miles (2,847 kilometres). The direct flight time is roughly 4 hours 25 minutes.
Flights from Fort McMurray, Canada - Fort McMurray Airport (YMM) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,446 miles (2,328 kilometres). The direct flight time is roughly 3 hours 42 minutes.
Flights from Comox, Canada - Comox Airport (YQQ) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,838 miles (2,957 kilometres). The direct flight time is roughly 4 hours 35 minutes.
Flights from Regina, Canada - Regina International Airport (YQR) to Chicago, Illinois (CHI) - The flight distance between these airports is 988 miles (1,590 kilometres). The direct flight time is roughly 2 hours 41 minutes.
Flights from Timmins, Canada - Victor M. Power Airport (YTS) to Chicago, Illinois (CHI) - The flight distance between these airports is 555 miles (893 kilometres). The direct flight time is roughly 1 hour 43 minutes.
Flights from Saskatoon, Canada - J.G. Diefenbaker Intl Airport (YXE) to Chicago, Illinois (CHI) - The flight distance between these airports is 1,125 miles (1,810 kilometres). The direct flight time is roughly 2 hours 59 minutes.
From Toronto (YYZ), Canada to Chicago, United States (ORD): C$254
Depart: 08 May 2024 · Return: 15 May 2024 Price found 26 Apr 2024, 10:19
From Montreal (YUL), Canada to Chicago, United States (ORD): C$260
Depart: 07 May 2024 · Return: 14 May 2024 Price found 26 Apr 2024, 05:47
From Calgary (YYC), Canada to Chicago, United States (ORD): C$313
Depart: 22 Aug 2024 · Return: 26 Aug 2024 Price found 25 Apr 2024, 16:26
From Vancouver (YVR), Canada to Chicago, United States (ORD): C$322
Depart: 14 May 2024 · Return: 28 May 2024 Price found 26 Apr 2024, 09:12
From Edmonton (YEG), Canada to Chicago, United States (ORD): C$404
Depart: 04 Jul 2024 · Return: 18 Jul 2024 Price found 26 Apr 2024, 05:57
From Ottawa (YOW), Canada to Chicago, United States (MDW): C$462
Depart: 07 Jun 2024 · Return: 10 Jun 2024 Price found 26 Apr 2024, 15:40
From Winnipeg (YWG), Canada to Chicago, United States (MDW): C$464
Depart: 11 Jun 2024 · Return: 15 Jun 2024 Price found 26 Apr 2024, 06:46
From Halifax (YHZ), Canada to Chicago, United States (MDW): C$485
Depart: 07 Jun 2024 · Return: 20 Jun 2024 Price found 26 Apr 2024, 13:21
From Regina (YQR), Canada to Chicago, United States (ORD): C$494
Depart: 22 May 2024 · Return: 26 May 2024 Price found 26 Apr 2024, 15:49
From Quebec (YQB), Canada to Chicago, United States (MDW): C$517
Depart: 12 May 2024 · Return: 16 May 2024 Price found 26 Apr 2024, 12:53
From Kelowna (YLW), Canada to Chicago, United States (ORD): C$578
Depart: 22 May 2024 · Return: 03 Jun 2024 Price found 26 Apr 2024, 09:55
From Saskatoon (YXE), Canada to Chicago, United States (ORD): C$694
Depart: 28 May 2024 · Return: 03 Jun 2024 Price found 26 Apr 2024, 12:03
From St John's (YYT), Canada to Chicago, United States (MDW): C$708
Depart: 30 Jul 2024 · Return: 06 Aug 2024 Price found 26 Apr 2024, 15:46
From Victoria (YYJ), Canada to Chicago, United States (MDW): C$746
Depart: 09 Jan 2025 · Return: 12 Jan 2025 Price found 25 Apr 2024, 11:46
From Yellowknife (YZF), Canada to Chicago, United States (MDW): C$865
Depart: 30 Jul 2024 · Return: 06 Aug 2024 Price found 26 Apr 2024, 12:01
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