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Cheapest Airline Tickets to Chicago, Illinois (CHI) in 2024/2025 from Canada

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How to find flight deals to Chicago, Illinois:

How to find flight deals to Chicago, Illinois:

1. Enter your search requirements for Chicago, Illinois

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

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

How to find flight deals to Chicago, Illinois:

3. Book your Chicago, Illinois flight at the cheapest price

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Map of Chicago, Illinois

How to find cheap and flexible flights to Chicago, Illinois - Q & A

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.

Which month is cheapest to fly to Chicago, Illinois?

The cheapest month of the year to fly to Chicago, Illinois is typically January.

What is the cheapest flight to Chicago, Illinois that we have found?

The best price we found is for C$240 from Calgary to Chicago.

Which popular airlines fly to Chicago, Illinois?

Some popular airlines include: WestJet, United, Spirit Airlines, Porter Airlines (Canada) Ltd, Delta, Canadian North, Bearskin Airlines, American Airlines, Alaska Airlines, Air Canada, Aeromexico.

What is considered a good price to Chicago, Illinois?

A good price for a flight to Chicago is C$216 - C$264.

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.

Things to do in Chicago, Illinois

Willis Tower

Super-tall skyscraper with city vistas

Navy Pier

Destination with rides, shops & food

Millennium Park

Green space with art, theater & ice rink

Cloud Gate

Mirrored, bean-shaped sculpture

The Art Institute of Chicago

Renowned art museum with global works

875 North Michigan Avenue

Sky-high city views from 94th-floor deck

Shedd Aquarium

Aquatic creatures from around the world

Skydeck Chicago

Panoramic views from 1353 feet above

Grant Park

Home to numerous Downtown attractions

Lincoln Park Zoo

Free zoo with an interactive farm

Magnificent Mile

Posh shops & the John Hancock Center

Field Museum

State-of-the-art science museum

Adler Planetarium

Museum with high-tech exhibits & shows

Wrigley Field

Cubs’ historic ballpark

360 CHICAGO

Observatory with tilting glass platform

Buckingham Fountain

Elaborate rococo landmark from 1927

Chicago Riverwalk

Scenic walkway along the Chicago River

Chicago Cultural Center

Free cultural exhibits, concerts & more

Museum of Science and Industry, Chicago

Interactive educational museum

Crown Fountain

Large LED sculpture with reflecting pool

City Gallery in the Historic Water Tower

Art gallery inside a historic landmark

Chicago Architecture Center

Urban design organization

Brookfield Zoo

Sprawling zoo with thousands of animals

Chicago Children's Museum

Hands-on-experiences for kids

Jay Pritzker Pavilion

Bandshell in the park with entertainment

Frank Lloyd Wright Home and Studio

The famed Prairie-style architect’s home

Lincoln Park Conservatory

Thousands of plants under a glass dome

Chicago History Museum

Chicago history brought to life

Garfield Park Conservatory

Gardens, athletic fields, fishing & more

Frederick C. Robie House

Frank Lloyd Wright-designed landmark

Oak Street Beach

Sandy city beach with lifeguards

North Avenue Beach

Popular summer spot with dining & stores

Maggie Daley Park

Busy hangout with playgrounds & skating

Peggy Notebaert Nature Museum

Environment-focused kid-friendly museum

Museum Campus

Lakefront park with famed institutions

Lurie Garden

5-acre urban botanical park

Tribune Tower

Skyscraper with French Gothic elements

Lakefront Trail

Extensive path with water & city views

The Richard H. Driehaus Museum

Restored Gilded Age mansion

The Wrigley Building

Landmark 1920s skyscraper & clock tower

The 606

Recreational trail on a former rail line

Chicago Riverwalk

Food, art & entertainment on a riverwalk

Lincoln Park

Vast public space with a zoo & museums

Burnham Park

Landscaped green space & tennis courts

Wendella Tours & Cruises

Chicago River & Lake Michigan tours

Jackson Park

Green space with a beach & gardens

Rookery Building

Historic tower with notable lobby design

DuSable Bridge

Historic drawbridge with decorative work

DuSable Museum of African American History

Exhibits covering art, culture & history

Oriental Institute Museum

Middle Eastern art & antiquities

Jane Addams Hull-House Museum

Memorial to social reformer Jane Addams

Chicago Board of Trade Building

Art deco tower crowned with Ceres statue

Northerly Island

Concert, music venue, and planetarium

Gold Coast

Stately mansions & Oak Street Beach

Marina City Goldberg

Architecture, ludwig mies van der rohe, marina, and modern architecture

Glessner House

Landmark 19th century house museum

BP Pedestrian Bridge

Winding footbridge by architect Gehry

Pullman National Monument

Monument, history, park, and architecture

The Merchandise Mart

Venue for home showrooms & trade shows

McCormick Tribune Plaza

Park with ice skating & a restaurant

Bahá'í House of Worship

1953 temple with intricate facade

Untitled by Picasso

50-ft. steel sculpture by iconic artist

Chicago Pedway

Architecture

Aon Center

Modern architecture and architecture

International Museum of Surgical Science

Dedicated to the history of surgery

Museum of Contemporary Photography

Rotating shows plus events & programs

Unity Temple

Frank lloyd wright and architecture

Graceland Cemetery

Arboretum & renowned burial place

Alfred Caldwell Lily Pool

Tranquil space with a pond & vegetation

Ohio Street Beach

Swimming spot with city skyline views

National Museum of Mexican Art

Mexican & Mexican-American artworks

Montrose Beach

Beach and kitesurfing

Oz Park

Wizard of Oz-themed playground & park

Chicago Trolley & Double Decker Co

Hop-on/hop-off city highlights tours

I Visit Chicago

Point of interest

Humboldt Park

Park and architecture

Ping Tom Memorial Park

River views, kayak rentals & playground

Montrose Beach

Seasonal swimming beach with amenities

American Writers Museum

Museum and literature

Promontory Point

Picnic spot on a man-made peninsula

Smart Museum of Art

Art & design, from ancient to modern

Rivers Casino Des Plaines

Gambling, dining & entertainment

Monadnock Building

Office block, once the world's largest

Henry B. Clarke House

Chicago's oldest surviving home

American Girl Place Chicago

Specialty dolls with historic relevance

Chicago Symphony Orchestra

Home to the Chicago Symphony Orchestra

North Park Village Nature Center

Nature preserve & educational center

Holy Name Cathedral

Cathedral, gothic architecture, and architecture

S. R. Crown Hall

Ludwig mies van der rohe, wassily kandinsky, modern architecture, and architecture

Newberry Library

Large research collection & rare books

Calder's Flamingo

Monumental 1974 abstract sculpture

Des Plaines River Trail

Cycling, trail running, river, running, and hiking

Weather in Chicago, Illinois

Clear
Clear

15.6 °C

Thu, 23 May 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

Flight Distance and Flying Time to Chicago, Illinois

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

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.

Travel Videos About Chicago, Illinois

Cheapest flight routes found to Chicago, Illinois

From Calgary

From Calgary (YYC), Canada to Chicago, United States (ORD): C$240

Depart: 20 Aug 2024 · Return: 24 Aug 2024 Price found 22 May 2024, 10:02

From Montreal

From Montreal (YUL), Canada to Chicago, United States (MDW): C$315

Depart: 01 Jul 2024 · Return: 09 Jul 2024 Price found 21 May 2024, 17:03

From Vancouver

From Vancouver (YVR), Canada to Chicago, United States (ORD): C$324

Depart: 27 Aug 2024 · Return: 30 Aug 2024 Price found 22 May 2024, 01:44

From Halifax

From Halifax (YHZ), Canada to Chicago, United States (MDW): C$325

Depart: 09 Jul 2024 · Return: 24 Jul 2024 Price found 19 May 2024, 06:14

From Saskatoon

From Saskatoon (YXE), Canada to Chicago, United States (ORD): C$333

Depart: 10 Jun 2024 · Return: 18 Jun 2024 Price found 21 May 2024, 08:19

From Edmonton

From Edmonton (YEG), Canada to Chicago, United States (ORD): C$339

Depart: 06 Jun 2024 · Return: 11 Jun 2024 Price found 20 May 2024, 08:43

From Winnipeg

From Winnipeg (YWG), Canada to Chicago, United States (MDW): C$362

Depart: 27 May 2024 · Return: 29 May 2024 Price found 22 May 2024, 19:51

From Regina

From Regina (YQR), Canada to Chicago, United States (ORD): C$362

Depart: 03 Jul 2024 · Return: 10 Jul 2024 Price found 23 May 2024, 04:23

From Kelowna

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

Depart: 17 Jun 2024 · Return: 25 Jun 2024 Price found 22 May 2024, 19:22

From Ottawa

From Ottawa (YOW), Canada to Chicago, United States (MDW): C$429

Depart: 12 Jul 2024 · Return: 14 Jul 2024 Price found 22 May 2024, 17:07

From Quebec

From Quebec (YQB), Canada to Chicago, United States (MDW): C$437

Depart: 13 Jun 2024 · Return: 15 Jun 2024 Price found 22 May 2024, 21:04

From Victoria

From Victoria (YYJ), Canada to Chicago, United States (ORD): C$451

Depart: 29 Jul 2024 · Return: 09 Aug 2024 Price found 22 May 2024, 23:45

From Thunder Bay

From Thunder Bay (YQT), Canada to Chicago, United States (MDW): C$542

Depart: 24 Jun 2024 · Return: 26 Jun 2024 Price found 20 May 2024, 01:48

From Moncton

From Moncton (YQM), Canada to Chicago, United States (MDW): C$548

Depart: 25 Aug 2024 · Return: 26 Aug 2024 Price found 22 May 2024, 11:59

From St John's

From St John's (YYT), Canada to Chicago, United States (ORD): C$687

Depart: 11 Sep 2024 · Return: 18 Sep 2024 Price found 20 May 2024, 15:42

From Yellowknife

From Yellowknife (YZF), Canada to Chicago, United States (ORD): C$791

Depart: 30 Jul 2024 · Return: 06 Aug 2024 Price found 20 May 2024, 12:04

From Timmins

From Timmins (YTS), Canada to Chicago, United States (ORD): C$831

Depart: 30 Aug 2024 · Return: 03 Sep 2024 Price found 20 May 2024, 22:58

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