Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights


Selected fares from Chicago to Winnipeg

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

Route Information for Flights from Chicago to Winnipeg

Origin Airport IATA Code ORD
Destination Airport IATA Code YWG
Flight Price $472
Distance 1,130 km

Chicago (CHI) to Winnipeg (YWG)

Are you flying to Winnipeg 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 in the right spot to score a killer deal on your upcoming flight from Chicago. Whether you fancy yourself a top-seeded ticket master or you're new to the jet-setting scene, read below to score the best deal on your next flight.

How do I get the best price on my flight from CHI to YWG?

We've been doing this for a long time, which means getting that great deal on a Winnipeg flight is easy-peasy. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.

What is the cheapest day to fly?

With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:

  • Tuesday and Wednesday—You know how most stores are not crowded midweek? Same thing here. So, get on while the getting is good.
  • Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your vacay by a day and increase your savings.
  • Monday through Thursday—If you're flying internationally, deals are often available when departing these days.

Can staying the weekend get me a cheaper ticket?

If you stay through the weekend, generally that return ticket to CHI can be cheaper since you'll be leaving earlier in the week. All those business travelers have less flexible itineraries, so that means savings for you. 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 vacationers aren't traveling to certain locations. So when it's chilly, most people head to warmer places like the Caribbean, Mexico, Hawaii, etc., just like the birds (they had it figured out). But during the summer months, you'll find that Europe is really popular. You can usually save on your ticket when you fly when everyone else isn't.

Jump on that great rate

You're not the only one seeking a great bargain on a flight from Chicago to Winnipeg. You might miss out on your opportunity to get the carrier and the times you need.

Are there any other ways to save?

We think the Hotwire Hot Rate is one of the best deals out there, although we may be slightly biased. You can get one of our best rates on a flight from Chicago (CHI) to Winnipeg (YWG). After you book, you'll get the time and name of the airline, but with a little risk you can get huge savings.

Book your flight today

Use our guide before you book your upcoming flight from Chicago to Winnipeg. You may have enough money back in your hand to add something that makes this vacay extra awesome ... or you can roll that money over and put it toward your next flight out of Chicago.

Map

^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.