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 and save!
Cheap airfares from /OW are provided by . This flight is going on , from () airport and arrives to () at so it makes 0 hours and 0 minutes. This is a oneway flight. Date posted: 31 Dec 1969
Price evolution for flights From Winnipeg To Chicago
Recent Deals on Flights from Winnipeg to Chicago:Roundtrip / Oneway
- $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 - We are sorry but currently there are no roundtrip offers for flights from Winnipeg to Chicago.
Please visit this page again later or try out our merchant comparison search. Good luck!
Recently found cheap flight deals
Phoenix To San Salvador Multiple Airlines airfares from Phoenix in March
$1110 Depart: 03/12/2025
Return: 03/25/2025
provided by Cheapoair.com
Santa Barbara To Seattle Alaska Airlines airfares from Santa Barbara in June
$774 Depart: 06/10/2024
Return: 06/16/2024
provided by Cheapoair.com
Baltimore To Florence Multiple Airlines airfares from Baltimore in September
$1925 Depart: 09/11/2024
Return: 09/17/2024
provided by Cheapoair.com
Boston To Maui Alaska Airlines airfares from Boston in December
$1508 Depart: 12/15/2023
Return: 12/30/2023
provided by Cheapoair.com
San Antonio To Fort Myers Alaska Airlines airfares from San Antonio in November
$1754 Depart: 11/24/2021
Return: 12/15/2021
provided by Cheapoair.com
Miami To Medellin Lan Airlines airfares from Miami in March
$326 Depart: 03/29/2025
Return: 04/05/2025
provided by Cheapoair.com
Phoenix To Sacramento Spirit Airlines airfares from Phoenix in March
$144 Depart: 03/17/2025
Return: 03/26/2025
provided by Cheapoair.com
Milwaukee To Atlanta Multiple Airlines airfares from Milwaukee in March
$174 Depart: 03/31/2025
Return: 04/15/2025
provided by Cheapoair.com
Denver To San Jose Avianca Airlines airfares from Denver in February
$911 Depart: 02/25/2025
Return: 03/05/2025
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.