$180 Find cheap flights from Winnipeg to Chicago Midway Airport

In the last 3 days, the lowest price for a flight from Winnipeg to Chicago Midway Airport was $180 for a one-way ticket and $400 for a round-trip.

A passport is required to fly from Winnipeg to Chicago Midway Airport.

Winnipeg and Chicago Midway Airport are both served by 1 main airport. You will leave Winnipeg from Winnipeg and will be arriving at Chicago Midway.

We unfortunately don’t have that data for this specific route.

SkyTeam is the only airline alliance operating flights between Winnipeg and Chicago Midway Airport.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Chicago Midway Airport.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Winnipeg is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Winnipeg with another airline. Booking your flights between Winnipeg and MDW can sometimes prove cheaper using this method.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.