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Book Flights from Winnipeg to Chicago will help you to find the best deals on flights from Winnipeg to Chicago. With our search technology, effortlessly searching flight routes across hundreds of airlines has never been easier or more convenient. With, we aim to make it simple and quick to search, select and save on the flights that best suit your needs and budget.

No matter if you are traveling for business or pleasure, we offer a wide range of deals from business class discounts to last minute flight deals to destinations like Chicago. Whether you are planning ahead or looking for last minute tickets, CheapOair has the right flights at the right price. After booking your ticket, explore this page to view blog posts about this destination, learn more about hotels near CHI and read reviews from others who booked their flights with

Frequently Asked Questions - Winnipeg to Chicago Flights

  • When does the first flight of the day depart from YWG?

    7:16AM United Airlines Flight #7178

  • When does the last flight depart to CHI?

    5:31PM United Airlines Flight #844

  • What is the travel distance between Winnipeg and Chicago?

    717 miles

  • How many weekly flights are there between YWG to CHI?

    There are 3 weekly flights between YWG and CHI.

  • Which is the busiest day in terms of passengers traffic between YWG to CHI?


  • In last 30 days, what %age of CHI visitors spent less than 3 days in the city?

    100.00 %

  • Which is the nearest airport to Chicago, Illinois?

    Midway International Airport

  • Which is the nearest airport to Winnipeg, Canada?

    Winnipeg James Armstrong Richardson International Airport