Question 1

What are the most popular routes to and from Winnipeg?

Accepted Answer

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.

Question 2

What are the most popular routes to and from Chicago?

Accepted Answer

Travelers frequently search for route combinations, such as Chicago and Toronto, Montreal, Vancouver, Calgary, Kuwait City, Edmonton, Ottawa, Kelowna, Quebec City, Victoria, Saskatoon, Lima.

Question 3

What airports are near Winnipeg?

Accepted Answer

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.

Question 4

What airports are near Chicago?

Accepted Answer

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.

Question 5

What buses and trains depart from Winnipeg?

Accepted Answer

A number of bus and train companies depart from Winnipeg, including Via Rail Canada.

Question 6

Is it possible to combine flights, buses, and trains in one itinerary when traveling between Winnipeg and Chicago?

Accepted Answer

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.

Question 7

What is Virtual Interlining and how do I use it?

Accepted Answer

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.

Question 8

Which airlines fly between Winnipeg and Chicago?

Accepted Answer

Currently, you can fly between Winnipeg and Chicago with WestJet, Air Canada, Delta Air Lines, United Airlines, Flair Airlines.

Question 9

When's the best time to travel between Winnipeg and Chicago?

Accepted Answer

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.

Question 10

What flights operate between Winnipeg and Chicago?

Accepted Answer

Traveling between Winnipeg and Chicago, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What's more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

Question 11

How many airports are there near Winnipeg?

Accepted Answer

There are a number of airports in and around Winnipeg. The main one is Winnipeg James Armstrong Richardson International and other nearby airports include Winnipeg James Armstrong Richardson International, Grand Forks International, Thief River Falls Regional, Brandon Municipal, Kenora

Question 12

How many airports are there near Chicago?

Accepted Answer

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include 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.

Question 13

Is it possible to reach Winnipeg by bus or train?

Accepted Answer

Yes, Winnipeg has great ground transport connections with the rest of the world. Our price graph doesn't just show prices for flights to and from Winnipeg, it also shows buses and trains.

Question 14

What time do nonstop (direct) flights between Winnipeg and Chicago depart?

Accepted Answer

This depends on the airline's flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Winnipeg, such as morning, afternoon, evening, or night, or select the exact hours for departure.

Question 15

What time do nonstop (direct) flights between Winnipeg and Chicago arrive?

Accepted Answer

This depends on the airline's flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

Question 16

What time do flights between Winnipeg and Chicago depart?

Accepted Answer

This depends on the airline's flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Winnipeg, such as morning, afternoon, evening, or night, or select the exact hours for departure.

Question 17

What time do flights between Winnipeg and Chicago arrive?

Accepted Answer

This depends on the airline's flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

Cheapest one-way trip	$386
Cheapest round-trip	$555
Average round-trip	$799
Most popular airline	WestJet

Name	Carrier code	IATA Code	Passport needed during booking	Online check-in available
WestJet	WJA	WS	No	Opens 24 days before flight Closes 1 hours before flight
Air Canada	ACA	AC	Yes	No
Delta Air Lines	DAL	DL	Yes	Opens 24 days before flight Closes 1 hours before flight
United Airlines	UAL	UA	Yes	No
Flair Airlines	FLE	F8	Yes	Opens 24 days before flight Closes 1 hours before flight

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

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

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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