Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline United Airlines

The cheapest airline(s) flying from Winnipeg to Chicago is United Airlines.

  • United Airlines United Airlines
  • Air Canada Air Canada
  • WestJet WestJet
  • Porter Airlines Porter Airlines
Cheapest Month February

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Winnipeg to Chicago is February.

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Winnipeg to Chicago is Friday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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  • Availability
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  • 14:15 YWG
    16:45 ORD
    2Hrs, 30m Direct
  • YWGWinnipeg J.A. Richardson Intl Airport 14:15 - ORD 16:45 2h 30m Direct
  • YWGWinnipeg J.A. Richardson Intl Airport 14:15
  • ORDChicago O'Hare International Airport 16:45
  • 2h 30m
  • Direct
  • United Airlines (UA 5639)Embraer 175
  • United Airlines (UA 5639)
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    • -
  • Embraer 175
  • 14:15 YWG
    16:45 ORD
    2Hrs, 30m Direct
  • YWGWinnipeg J.A. Richardson Intl Airport 14:15 - ORD 16:45 2h 30m Direct
  • YWGWinnipeg J.A. Richardson Intl Airport 14:15
  • ORDChicago O'Hare International Airport 16:45
  • 2h 30m
  • Direct
  • United Airlines (UA 5639)Embraer 175
  • United Airlines (UA 5639)
    • -
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  • Embraer 175
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What’s the fastest flight time from Winnipeg to Chicago?

The fastest flight time for direct flights from Winnipeg to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.

How far is Chicago from Winnipeg?

The flight distance between Winnipeg and Chicago is 1154km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 14:15. The last flight of the day departs at 14:15. See the full list of flight times on Wego.

How many airlines offer direct flights from Winnipeg to Chicago?

There are 1 airlines that offer direct flights from Winnipeg to Chicago. Find out the list of airlines on Wego.