Cheap flights from Winnipeg, Canada to Chicago, IL
Flights starting at CA$207. Choose between WestJet, Frontier Airlines, or United Airlines to find the best price.
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Tips to know when travelling to Chicago
Cheapest one-way trip | CA$207 |
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Cheapest round-trip | CA$358 |
Average round-trip | CA$566 |
Includes rare itinerary | Travel hack |
Most popular airline | WestJet |
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Check-in for a flight from Winnipeg to Chicago
Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
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WestJet | WJA | WS | No | Opens 24 days before flight Closes 1 hours before flight |
Frontier Airlines | FFT | F9 | No | Opens 24 days before flight Closes 1 hours before flight |
United Airlines | UAL | UA | Yes | No |
Air Canada | ACA | AC | Yes | No |
Flair Airlines | FLE | F8 | Yes | Opens 24 days before flight Closes 1 hours before flight |
United States COVID-19 travel restrictions

Most travellers from Winnipeg, YWG can enter Chicago, ORD, but there are restrictions.
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Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.
Frequently asked questions
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The nearest countries with flights to Chicago
Here is a list of countries people are flying fromOther destination countries from Winnipeg
Here is a list of countries people are flying toAirports near Winnipeg
- Winnipeg James Armstrong Richardson International
- Grand Forks International
- Brandon Municipal
- Thief River Falls Regional
- Kenora
- Devils Lake Regional