Calgary to Chicago, IL flights from $279

Flights starting at $279. Choose between Air Canada, WestJet, or Frontier Airlines to find the best price.

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Travelers usually depart from Calgary International, or Calgary - Centex Memorial Drive when they travel from Calgary to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Downtown Greyhound Station, or Chicago Rockford International. The distance between Calgary and Chicago is 2226 km. The most popular airlines for this route are Air Canada, WestJet, Frontier Airlines, United Airlines, and Delta Air Lines. Calgary and Chicago have 401 direct flights per week.

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Direct flights3333333
Fly direct with

American Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Air Canada on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

United Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Check-in for a flight from Calgary to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Air CanadaACAACYesNo
WestJetWJAWSNoOpens 24 days before flight
Closes 1 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight

United States COVID-19 travel restrictions

Kiwi.com

Latest COVID-19 restrictions

United States

Kiwi.com/COVID-19/United States
  • Travel through the US land border is allowed for vaccinated travelers
  • Travel is allowed with restrictions for vaccinated travelers
  • No proof of negative pre-departure COVID-19 test results or recovery certificate is required for United States
  • No quarantine is required for vaccinated travelers
Latest COVID-19 travel restrictions in United States – 09/2022
Your trip summary

Most travelers from Calgary, YYC can enter Chicago, MDW, but there are restrictions.

Departure

Travel restrictions
  • Travel through the US land border is allowed for vaccinated travelers
  • Travel is allowed with restrictions for vaccinated travelers
  • No proof of negative pre-departure COVID-19 test results or recovery certificate is required for United States
  • No quarantine is required for vaccinated travelers
Visa requirements
  • No visa required
Forms and documents
  • Mandatory proof of COVID-19 vaccination is required for United States
  • Mandatory travel attestation form

Return

Visa requirements
  • No visa required
Forms and documents
  • Mandatory proof of vaccination for Canada
  • Mandatory contact information form via ArriveCAN for vaccinated travelers
Additional information
  • Masks are mandatory in certain settings

Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.

Learn more about COVID-19 restrictions in United States in our dedicated Stories article.

Frequently asked questions

How long does it take to travel from Calgary to Chicago?
A one-way nonstop (direct) flight between Calgary and Chicago takes around 3.4 hours.
What is the flight distance between Calgary and Chicago?
The flight distance between Calgary and Chicago is 2226 km.
What airlines offer nonstop (direct) flights between Calgary and Chicago?
Several carriers operate flights between Calgary and Chicago. Airlines offering nonstop (direct) flights include American Airlines, Air Canada, United Airlines.
What are the most popular routes to and from Calgary?
Travelers frequently search for route combinations, such as Calgary and New York, Orlando, Las Vegas, Denver, Miami, Los Angeles, Atlanta, Mexico City, Bogotá, Dallas, Phoenix, Philadelphia, San Francisco, Cancún, Houston, San Juan, Washington, D.C., Dhaka, Fort Lauderdale, London.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and Toronto, Montreal, Vancouver, Kuwait City, Winnipeg, Edmonton, Ottawa, Kelowna, Quebec City, Victoria, Saskatoon, Lima.
What airports are near Calgary?
The main airport in Calgary is Calgary International. It is also served by Calgary International, Lethbridge.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, Dane County Regional, Central Illinois Regional, General Wayne A. Downing Peoria International, South Bend International, Fort Wayne International, Quad City International, Muskegon County, Decatur.
What buses and trains depart from Calgary?
A number of bus and train companies depart from Calgary, including Cold Shot Bus.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between Calgary and Chicago?
Yes, it's possible to combine different modes of transport between Calgary and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Calgary and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.
What is Virtual Interlining and how do I use it?
Which airlines fly between Calgary and Chicago?
When's the best time to travel between Calgary and Chicago?
What flights operate between Calgary and Chicago?
How many airports are there near Calgary?
How many airports are there near Chicago?
Is it possible to reach Calgary by bus or train?
What time do nonstop (direct) flights between Calgary and Chicago depart?
What time do nonstop (direct) flights between Calgary and Chicago arrive?
What time do flights between Calgary and Chicago depart?
What time do flights between Calgary and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.

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