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Cheap ORD to YWG Flights

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

Chicago to Winnipeg route information

Origin Airport O'Hare Intl.
Destination Airport Winnipeg James Armstrong Richardson Intl.
Airlines Serving Air Canada, Delta, United, WestJet
Flight Price $425
Distance 706 mi



Cheap ORD to YWG Flights

  • Question : Which airline has the least delays from Chicago to Winnipeg?
    Answer : Booking with SkyWest Airlines means you will arrive to Winnipeg pretty close to the time your ticket states. In fact, this timely airline has a 70% on-time average.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Chicago to Winnipeg is on Wednesday. If you would like to save a bit of money on your next flight look for flights on Wednesday.
  • Question : Can I change the date of my flight?
    Answer : You sure can and you may save money by changing when you take off. The lowest-cost day to fly in August is Wednesday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.
  • Question : What day has the most flight time options?
    Answer : Saturday has the greatest variety of flight times for Chicago to Winnipeg with six. Friday currently offers the least amount of flight times with only five options.
  • Question : How many flights are there per day from Chicago to Winnipeg?
    Answer : The number of flight times varies by day of the week, but on average, ORD to YWG sees five different options. That is lower than the national average of nine.
  • Question : How long is the flight from ORD to YWG?
    Answer : United Airlines can get you there in two hours and 24 minutes. So, if you were to leave Chicago at 7:40 PM CDT, you would arrive in Winnipeg at 10:04 PM CDT. Just enough time if you want to catch up on your reading before your plane touches down.
  • Question : How long does it take to fly from Chicago to Winnipeg?
    Answer : United Airlines currently holds the fastest travel time with two hours and 24 minutes. For example, you would arrive in Winnipeg at 10:04 PM CDT if you left Chicago at 7:40 PM CDT.

Chicago to Winnipeg Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Winnipeg will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Winnipeg.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at, we’ll pair you up with ORD to YWG flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to YWG with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Sep 10, 2018

Time between connecting flight a bit too short. Had to sprint to connecting gate. This is hard for seniors.

Sep 2, 2018

Connection of flights were too long

Aug 2, 2018

Traveling with my handicapped 91year old mother. Wheelchair requested. Was assigned seats 12A &12B! Called to be reassigned. United gave my Expedia rep seats 3A &3B...then after we boarded a young couple flying STANDBY were put into seats 1A &1B! Row 1 should have been given to a handicapped, wheelchair customer!!

Jul 3, 2018

Very hard one wheel landing at ORD.

Jun 12, 2018

Seats too cramped. No leg room. Good thing it was a short flight.

Feb 25, 2018

I loved that my Expedia booking actually gave me a confirmation with the airline to check in directly! Will always use Expedia for the ease of it!!

Nov 24, 2016

Agent moved our seata so my wife and i could ait together