Cheap flights from Winnipeg to Chicago
Travel > North America > United States > Winnipeg to Chicago flights
Check our current prices for flights from Winnipeg to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Winnipeg to Chicago, you will need to run a search below.
Search and Compare cheap Flights
Book your flight now with Cheapoair.com and save!
Cheap Chicago airfares from $522/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/19/2025, 08:50 am from Winnipeg Intl (YWG) airport and arrives at Chicago Midway (MDW) at 02:15 pm. The flight time is 5 hours and 25 minutes. The Returning flight departes on 04/01/2025, 09:25 am (other return dates are also available). Date posted: 24 Jan 2025
Price evolution for flights From Winnipeg To Chicago
Recent Deals on Flights from Winnipeg to Chicago:Roundtrip / Oneway
- $522
Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 03/19/2025 08:50 am Chicago, IL (MDW) Winnipeg, MB (YWG) 04/01/2025 09:25 am - $525
Porter Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 03/19/2025 05:00 am Chicago, IL (MDW) Winnipeg, MB (YWG) 04/01/2025 05:35 pm - $216 Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (ORD) 06/11/2025 08:30 am - $337 Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 06/11/2025 08:50 am - $388 Porter Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 06/11/2025 05:00 am
Recently found cheap flight deals
Cincinnati To Albany Frontier Airlines airfares from Cincinnati in June
$1168 Depart: 06/22/2022
Return: 06/27/2022
provided by Cheapoair.com
Chicago To Natal Multiple Airlines airfares from Chicago in August
$1340 Depart: 08/21/2024
Return: 09/03/2024
provided by Cheapoair.com
Fort Myers To Rome British Airways airfares from Fort Myers in April
$1103 Depart: 04/08/2025
Return: 04/21/2025
provided by Cheapoair.com
Las Vegas To Oslo Multiple Airlines airfares from Las Vegas in October
$1703 Depart: 10/25/2023
Return: 11/06/2023
provided by Cheapoair.com
Chicago To Great Falls Alaska Airlines airfares from Chicago in July
$791 Depart: 07/25/2024
Return: 08/02/2024
provided by Cheapoair.com
Phoenix To Myrtle Beach Spirit Airlines airfares from Phoenix in March
$381 Depart: 03/17/2025
Return: 03/22/2025
provided by Cheapoair.com
Providence To Lisbon Multiple Airlines airfares from Providence in May
$2161 Depart: 05/21/2024
Return: 06/05/2024
provided by Cheapoair.com
Houston To Jeddah Qatar Airways airfares from Houston in February
$1059 Depart: 02/02/2025
Return: 02/08/2025
provided by Cheapoair.com
Reno To Phoenix Multiple Airlines airfares from Reno in May
$253 Depart: 05/10/2023
Return: 05/20/2023
provided by Cheapoair.com
Specify your search details. Browse the cheapest flights from Winnipeg to Chicago, Chicago hotel rooms and Winnipeg to Chicago vacation packages from the most popular providers, airline consolidators and travel search engines.
Know what to do when flying to Chicago?
Chicago Travel Guide Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals. Though [...]Chicago History The site where Chicago stands had long been considered as an important portage point on the water route linking the Great Lakes with the Mississippi river. Aside from this important fact, there are a lot of interesting things you need to know [...]
Chicago Sightseeing The rich cultural heritage of Chicago is depicted in its famous sights. Other tourist attractions in the city can be seen in zoos and parks as well. If you are thinking about visiting, it will help if you take a look at some of the travel [...]
Chicago Nightlife Chicago is one of the cities blessed with a variety of nightlife options. Discos, clubs, bars - name it and the place will certainly give you the pleasure you are looking for. You will surely dance the night away as you listen to the music [...]
© Copyright 2004 - 2025 Travelgrove, Inc.