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◊ Applies to bookings for 3+ travelers. Book by Sep 30, 2018.  Learn more
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Book Flights from Chicago to Winnipeg will help you to find the best deals on flights from Chicago to Winnipeg. 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 Winnipeg. 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 YWG and read reviews from others who booked their flights with

  • When does the first flight of the day depart from CHI? 7:50AM United Airlines Flight #8097
  • When does the last flight depart to YWG? 7:35PM United Airlines Flight #5775
  • What is the travel distance between Chicago and Winnipeg?717 miles
  • What is the price range for flights from CHI to YWG? C$500 - C$500
  • How many weekly flights are there are between CHI to YWG?There are 13 weekly flights between CHI and YWG.
  • How many daily flights fly between Chicago to Winnipeg? There are 1 daily flights between CHI and YWG
  • Which is the busiest day in terms of passengers flying from CHI to YWG?Wednesday
  • Which is the nearest airport to Winnipeg, Canada?Winnipeg James Armstrong Richardson International Airport
  • Which is the nearest airport to Chicago, Illinois?Midway International Airport
  • How much does the cheapest return flight from CHI to YWG cost? C$500

User Reviews

4Weather turned out to be very cool

Flights both ways were good, and on time. The early departure from Hamilton turned out to be too early, but everything else was good. - James  Sep 17, 2018
5I love Winnipeg

My trip to Winnipeg was fantastic I got to see my family that I haven,t seen in 10 years and I couldn't have been able to afford it if it wasn't for CheapOair.You found me the best price that was affordable for my budget Thank you CheapOair. - Nolan  Sep 11, 2018

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