Cheap flights from Winnipeg to Chicago, IL

Flights starting at $386. Choose between WestJet, Air Canada, or Delta Air Lines to find the best price.

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Travelers usually depart from Winnipeg James Armstrong Richardson International, or Winnipeg Train Station when they travel from Winnipeg to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Rockford International, or Chicago Downtown Greyhound Station. The most popular airlines for this route are WestJet, Air Canada, Delta Air Lines, United Airlines, and Flair Airlines. Winnipeg and Chicago have 401 direct flights per week.

Check-in for a flight from Winnipeg to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
WestJetWJAWSNoOpens 24 days before flight
Closes 1 hours before flight
Air CanadaACAACYesNo
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Flair AirlinesFLEF8YesOpens 24 days before flight
Closes 1 hours before flight

United States COVID-19 travel restrictions

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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
  • No quarantine required for vaccinated travelers
Latest COVID-19 travel restrictions in United States – 08/2022
Your trip summary

Most travelers from Winnipeg, YWG 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
  • No quarantine required for vaccinated travelers
Visa requirements
  • No visa required
Forms and documents
  • Mandatory proof of vaccination for the 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 during travel and in some provinces

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

What are the most popular routes to and from Winnipeg?
Travelers frequently search for route combinations, such as Winnipeg 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, Calgary, Kuwait City, Edmonton, Ottawa, Kelowna, Quebec City, Victoria, Saskatoon, Lima.
What airports are near Winnipeg?
The main airport in Winnipeg is Winnipeg James Armstrong Richardson International. It is also served by Winnipeg James Armstrong Richardson International, Grand Forks International, Thief River Falls Regional, Brandon Municipal, Kenora.
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, General Wayne A. Downing Peoria International, South Bend International, Fort Wayne International, Central Illinois Regional, Quad City International, Kalamazoo/Battle Creek International, Decatur.
What buses and trains depart from Winnipeg?
A number of bus and train companies depart from Winnipeg, including Via Rail Canada.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between Winnipeg and Chicago?
Yes, it's possible to combine different modes of transport between Winnipeg and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Winnipeg 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?
Virtual Interlining provides a revolutionary way of traveling. You can combine different modes of transport like flights, trains, and buses into one itinerary. And this often saves money. Thanks to the world's largest carrier database, the Kiwi.com search function enables anyone to mix and match different modes of transport easily.
Which airlines fly between Winnipeg and Chicago?
Currently, you can fly between Winnipeg and Chicago with WestJet, Air Canada, Delta Air Lines, United Airlines, Flair Airlines.
When's the best time to travel between Winnipeg and Chicago?
If you don’t have specific dates for your trip between Winnipeg and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.
What flights operate between Winnipeg and Chicago?
How many airports are there near Winnipeg?
How many airports are there near Chicago?
Is it possible to reach Winnipeg by bus or train?
What time do nonstop (direct) flights between Winnipeg and Chicago depart?
What time do nonstop (direct) flights between Winnipeg and Chicago arrive?
What time do flights between Winnipeg and Chicago depart?
What time do flights between Winnipeg 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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