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Selected fares from Winnipeg to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Route Information for Flights from Winnipeg to Chicago

Origin Airport IATA Code YWG
Destination Airport IATA Code ORD
Flight Price $275
Distance 1,130 km

Winnipeg (YWG) to Chicago (CHI)

Are you flying to Chicago for a much-needed vacation or is it about time for you to have a family reunion? Or maybe you're traveling for work? Hey, anything that gets you away from that desk is a win in our books. You're on the perfect page to snatch a killer rate on your upcoming flight from Winnipeg. Whether you call yourself a top-seeded ticket master or only have a few trips under your wing, read on to see how to book a too-good-to-be-true flight.

How can you get a great rate on tickets from Winnipeg to Chicago?

Hotwire has been in the game a long time, which means getting that great deal on a Chicago flight is easy-peasy. You'll make spending less look so very good with a few simple tips and tricks.

Which days of the week are cheapest to fly?

It pays to be a weekday warrior. Tuesday and Wednesday typically have the best rates. Next in line are Thursday and, surprisingly, Saturday. Most people like to fly back from their trip on Sunday so you can save by leaving a day earlier.

Can staying the weekend get me a cheaper ticket?

Staying the weekend at your destination, like Chicago, usually means lower airfare since most people fly during this time. Of course, we don't want to twist your rubber arm or anything.

Can you save while traveling during the off-peak season?

Off-peak and shoulder seasons are when most people aren't going to certain locations. So when it is chilly, most people head to warmer climates like the Caribbean, Mexico, Hawaii, etc., just like our feathered friends. But in the summer, you'll find that Europe is where it's at. You may not get the ideal weather, but you'll generally get better prices and be there when it is not flocked by out of towners.

Jump on that great rate

Airline carriers change their rates seemingly by the minute. If a price you love pops up, then book it! There are a lot of other people that are longing for a stellar bargain on a ticket from Winnipeg to Chicago. You might miss out on your opportunity to dial in the time and the flight you wanted.

Are there any other ways to save?

The Hotwire Hot Rate is what makes us stand out from the rest. It's one of our ways to help get you one of the best rates on a flight from Winnipeg (YWG) to Chicago (CHI). After your purchase, you'll get the time and name of the airline, but with a little risk you can get huge savings.

Book your flight today

We're here to help you save some money on your ticket to Chicago. These tips can get you that unreal rate. For traveler that likes to take it as it comes, and save while doing it, go for the Hotwire Hot Rate. You'll get your flight and have more coin in your hand to do Chicago the way you want. So say "Later" to Winnipeg and "Hello" to Chicago.

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^Savings based on all package bookings with Flight + Hotel made on Hotwire.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.