Question 1

How long does it take to travel from Winnipeg to Chicago?

Accepted Answer

A one-way nonstop (direct) flight between Winnipeg and Chicago takes around 2.6 hours.

Question 2

What is the flight distance between Winnipeg and Chicago?

Accepted Answer

The flight distance between Winnipeg and Chicago is 1139 km.

Question 3

What airlines offer nonstop (direct) flights between Winnipeg and Chicago?

Accepted Answer

Several carriers operate flights between Winnipeg and Chicago. Airlines offering nonstop (direct) flights include United Airlines, Air Canada.

Question 4

What are the most popular routes to and from Winnipeg?

Accepted Answer

Travelers frequently search for route combinations, such as Winnipeg and Toronto, Calgary, Edmonton, Vancouver, Ottawa, London, Montreal, Puerto Vallarta, Los Angeles, Las Vegas, Abbotsford, Kelowna, Cancún, Orlando, New York, Atlanta, Phoenix, Victoria, Manchester, Fort Lauderdale.

Question 5

What are the most popular routes to and from Chicago?

Accepted Answer

Travelers frequently search for route combinations, such as Chicago and London, Mexico City, New York, Guadalajara, Edinburgh, Dallas, Manchester, Morelia, Atlanta, Los Angeles, Houston, León, Leeds, Orlando, San Francisco, Philadelphia, Tampa, Miami, Monterrey, Birmingham.

Question 6

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, Thief River Falls Regional, Brandon Municipal, Grand Forks International, Kenora.

Question 7

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, Dane County Regional, South Bend International, General Mitchell International, Fort Wayne International, General Wayne A. Downing Peoria International, Quad City International, Central Illinois Regional, Muskegon County, Kalamazoo/Battle Creek International.

Question 8

Which airlines fly between Winnipeg and Chicago?

Accepted Answer

Currently, you can fly between Winnipeg and Chicago with WestJet, Air Canada, Porter Airlines, Frontier 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, Thief River Falls Regional, Brandon Municipal, Grand Forks International, 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, Dane County Regional, South Bend International, General Mitchell International, Fort Wayne International, General Wayne A. Downing Peoria International, Quad City International, Central Illinois Regional, Muskegon County, Kalamazoo/Battle Creek International.

Question 13

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 14

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 15

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 16

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	£165
Cheapest nonstop round-trip	£576
Cheapest round-trip	£322
Average round-trip	£332
Includes rare itinerary	Travel hack

Transport Option	Typical Time	Typical Cost	Frequency	Best For
CTA Blue Line to downtown	40-50 min	$5; standard fare	every 5–10 min (traffic dependent)	budget travelers to Loop
Pace Bus 250 to Metra	60-90 min	$2 – $5; combined bus and Metra fare	every 20–30 min (traffic dependent)	northwest suburbs connection
Taxi to downtown	35-70 min	$45 – $65; metered; varies by traffic	on-demand 24/7 (traffic dependent)	door-to-door with luggage
Ride-hailing (Uber/Lyft)	35-70 min	$35 – $75; surge pricing may apply	on-demand 24/7 (traffic dependent)	app-based convenience
Private transfer/shuttle	35-70 min	$60 – $120; pre-booked; fixed rate	by reservation (traffic dependent)	groups or business travel

Transport Option	Typical Time	Typical Cost	Frequency	Best For
CTA Orange Line to downtown	25-30 min	$5; standard fare	every 6–12 min (traffic dependent)	quick access to Loop
Taxi to downtown	20-45 min	$30 – $45; metered; varies by traffic	on-demand 24/7 (traffic dependent)	door-to-door convenience
Ride-hailing (Uber/Lyft)	20-45 min	$25 – $50; surge pricing may apply	on-demand 24/7 (traffic dependent)	flexible pickup location

Airline	Mon 13.07	Tue 14.07	Wed 15.07	Thu 16.07	Fri 17.07	Sat 18.07	Sun 19.07
Air Canada	2	2	2	2	2	1	---
United Airlines	---	---	---	---	---	1	2
Weekly flights: 14 total	Daily flights: 2 average	Most flights: Monday 2 flights

Airline	Mon 20.07	Tue 21.07	Wed 22.07	Thu 23.07	Fri 24.07	Sat 25.07	Sun 26.07
Air Canada	2	---	---	---	---	---	2
United Airlines	---	2	1	2	2	2	2
Weekly flights: 15 total	Daily flights: 2.14 average	Most flights: Monday 2 flights

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Company

Platform

Features

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Airline	Mon 27.07	Tue 28.07	Wed 29.07	Thu 30.07	Fri 31.07	Sat 01.08	Sun 02.08
Air Canada	2	2	2	2	2	2	2
United Airlines	2	2	2	2	2	2	1
Weekly flights: 27 total	Daily flights: 3.86 average	Most flights: Monday 2 flights

Airline	Mon 03.08	Tue 04.08	Wed 05.08	Thu 06.08	Fri 07.08	Sat 08.08	Sun 09.08
Air Canada	2	2	1	---	2	---	1
United Airlines	2	2	1	2	---	2	1
Weekly flights: 18 total	Daily flights: 2.57 average	Most flights: Monday 2 flights

Name	Carrier code	IATA Code	Passport needed during booking
WestJet	WJA	WS	No
Air Canada	ACA	AC	Yes
Porter Airlines	POE	PD	No
Frontier Airlines	FFT	F9	No
Flair Airlines	FLE	F8	Yes

Month	Average monthly max temperature	Average monthly min temperature
January	-1°C	-6°C
February	0°C	-5°C
March	6°C	0°C
April	11°C	5°C
May	17°C	10°C
June	22°C	16°C
July	26°C	20°C
August	25°C	19°C
September	22°C	16°C
October	15°C	10°C
November	8°C	3°C
December	2°C	-1°C