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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Winnipeg YWGAtlanta ATLWinnipeg YWG
CA$429
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Travelers usually depart from Winnipeg James Armstrong Richardson International, or Winnipeg Train Station when they travel from Winnipeg to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Downtown Greyhound Station, or Chicago Rockford International. The most popular airlines for this route are WestJet, Frontier Airlines, United Airlines, Air Canada, and Flair Airlines. Winnipeg and Chicago have 401 direct flights per week.

Check-in for a flight from Winnipeg to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
WestJetWJAWSNoOpens 24 days before flight
Closes 1 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Air CanadaACAACYesNo
Flair AirlinesFLEF8YesOpens 24 days before flight
Closes 1 hours before flight

United States COVID-19 travel restrictions

Your trip summary

Departure

Travel restrictions
  • Travel is allowed
  • Proof of pre-departure COVID-19 test is not required
  • Quarantine is not required
Visa requirements
  • Visa is not required

Return

Travel restrictions
  • Travel is allowed
  • Proof of pre-departure COVID-19 test is not required
  • Quarantine is not required
Visa requirements
  • Visa is not required

Frequently asked questions

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What time do flights between Winnipeg and Chicago depart?
What time do flights between Winnipeg and Chicago arrive?

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