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Cheap Flights from Chicago O'Hare International to Winnipeg

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Compare Chicago O'Hare International to Winnipeg flight deals

Find the cheapest month or even day of the year to fly to Winnipeg

Book the best Winnipeg fare with no extra fees

Flight deals from Chicago O'Hare International to Winnipeg

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International to Winnipeg? Find the lowest prices on one-way and return tickets right here.
Winnipeg.SAR 331 per passenger.Departing Tue, 25 Mar.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 25 Mar, arriving in Winnipeg.Price includes taxes and charges.From SAR 331, select.
Winnipeg.SAR 331 per passenger.Departing Tue, 1 Apr.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 1 Apr, arriving in Winnipeg.Price includes taxes and charges.From SAR 331, select.
Winnipeg.SAR 441 per passenger.Departing Tue, 17 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 17 Jun, arriving in Winnipeg.Price includes taxes and charges.From SAR 441, select.
Winnipeg.SAR 600 per passenger.Departing Wed, 30 Jul.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 30 Jul, arriving in Winnipeg.Price includes taxes and charges.From SAR 600, select.
Winnipeg.SAR 651 per passenger.Departing Mon, 4 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 4 Aug, arriving in Winnipeg.Price includes taxes and charges.From SAR 651, select.
Winnipeg.SAR 674 per passenger.Departing Fri, 16 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 16 May, arriving in Winnipeg.Price includes taxes and charges.From SAR 674, select.
Winnipeg.SAR 829 per passenger.Departing Wed, 3 Sep.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 3 Sep, arriving in Winnipeg.Price includes taxes and charges.From SAR 829, select.
Winnipeg.SAR 959 per passenger.Departing Wed, 3 Sep.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Wed, 3 Sep, arriving in Winnipeg.Price includes taxes and charges.From SAR 959, select.

Find the cheapest month to fly from Chicago O'Hare International to Winnipeg

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to Winnipeg flights are currently cheapest in March.
Mar
from SAR 331
Apr
from SAR 331
May
from SAR 674
Jun
from SAR 441
Jul
from SAR 600
Aug
from SAR 651
Sep
from SAR 829
Oct
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Nov
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Dec
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Jan
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Feb
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Direct flights from Chicago O'Hare International to Winnipeg

Chicago O'Hare International to Winnipeg: Alternative routes

Compare routes from Chicago O'Hare International to Winnipeg below. You may find an airport to fly into that's cheaper, faster, or easier than Winnipeg.

Chicago to Winnipeg: Flight information

The things to know before you go.
Cheapest flight foundSAR 331
Cheapest month to flyApril
Average flight time2 hrs, 32 mins
Most popular airlineAir New Zealand
Average flights per week43

Finding cheap flights from Chicago O'Hare International to Winnipeg: Frequently asked questions

The best price we found for a return flight from Chicago O'Hare International to Winnipeg is SAR 1,061. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 32 minutes is the average flight time from Chicago O'Hare International to Winnipeg.
Air New Zealand, Air Canada and United fly direct from Chicago O'Hare International to Winnipeg.
As of March 2025, there are 43 flights per week flying from Chicago O'Hare International to Winnipeg.
The cheapest month to fly from Chicago O'Hare International to Winnipeg is usually March 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to Winnipeg Airport on Monday, 21 April 2025.
Yes – the average flight time is 2 hours and 32 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Winnipeg but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Winnipeg is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Spirit Airlines and Air Canada offer the cheapest flight tickets to Winnipeg.

How to find cheap flights to Winnipeg from Chicago O'Hare International

Looking for cheap tickets from Chicago O'Hare International to Winnipeg? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago O'Hare International to Winnipeg. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Winnipeg from Chicago O'Hare International from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best Chicago O'Hare International-Winnipeg ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Winnipeg from Chicago O'Hare International.
  • Set up a Price Alert. You can easily track the fare of your cheap Chicago O'Hare International-Winnipeg flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Chicago O'Hare International and Winnipeg? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from Chicago O'Hare International and Winnipeg. We scour the internet for the best Business, Premium Economy and First Class flight fares to Winnipeg, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Chicago O'Hare International to Winnipeg flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

    • Combine your flight to Winnipeg from Chicago O'Hare International with hotels and car hire

    Once you've secured your cheap flight ticket from Chicago O'Hare International to Winnipeg, discover the best prices and exclusive rates for hotels in Winnipeg or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.