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Cheap Flights from Chicago to Winnipeg from $425

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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.

Sun, Sep 29 - Wed, Oct 2
ORD
Chicago
to
YWG
Winnipeg
$425

roundtrip

just found

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Tue, Aug 20 - Sun, Aug 25
ORD
Chicago
to
YWG
Winnipeg
$430

roundtrip

found 5 days ago

Open ORD to YWG flights search result page
Tue, Oct 22 - Thu, Oct 24
ORD
Chicago
to
YWG
Winnipeg
$430

roundtrip

found 14 hours ago

Open ORD to YWG flights search result page
Tue, Oct 22 - Thu, Oct 24
ORD
Chicago
to
YWG
Winnipeg
$431

roundtrip

found 14 hours ago

Open ORD to YWG flights search result page
Sun, Sep 29 - Wed, Oct 2
ORD
Chicago
to
YWG
Winnipeg
$432

roundtrip

just found

Open ORD to YWG flights search result page
Sun, Sep 29 - Wed, Oct 2
ORD
Chicago
to
YWG
Winnipeg
$433

roundtrip

just found

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Sat, Dec 7 - Tue, Dec 24
ORD
Chicago
to
YWG
Winnipeg
$434

roundtrip

found 21 hours ago

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Sun, Sep 29 - Wed, Oct 2
ORD
Chicago
to
YWG
Winnipeg
$435

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just found

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Sun, Sep 15 - Sat, Sep 21
ORD
Chicago
to
YWG
Winnipeg
$439

roundtrip

found 2 days ago

Open ORD to YWG flights search result page
Tue, Oct 22 - Thu, Oct 24
ORD
Chicago
to
YWG
Winnipeg
$439

roundtrip

found 14 hours ago

Open ORD to YWG flights search result page
Tue, Oct 22 - Thu, Oct 24
ORD
Chicago
to
YWG
Winnipeg
$440

roundtrip

found 14 hours ago

Open ORD to YWG flights search result page
Tue, Oct 22 - Thu, Oct 24
ORD
Chicago
to
YWG
Winnipeg
$441

roundtrip

found 14 hours ago

Open ORD to YWG flights search result page
Fri, Sep 13 - Wed, Sep 18
ORD
Chicago
to
YWG
Winnipeg
$443

roundtrip

found 2 days ago

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Mon, Oct 7 - Thu, Oct 10
ORD
Chicago
to
YWG
Winnipeg
$446

roundtrip

found 1 day ago

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Sun, Sep 15 - Sat, Sep 21
ORD
Chicago
to
YWG
Winnipeg
$449

roundtrip

found 2 days ago

Open ORD to YWG flights search result page
Wed, Oct 9 - Tue, Oct 15
ORD
Chicago
to
YWG
Winnipeg
$450

roundtrip

found 2 days ago

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Tue, Aug 13 - Fri, Aug 16
ORD
Chicago
to
YWG
Winnipeg
$451

roundtrip

found 6 days ago

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Mon, Oct 7 - Thu, Oct 10
ORD
Chicago
to
YWG
Winnipeg
$454

roundtrip

found 1 day ago

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Mon, Jan 6 - Mon, Jan 13
ORD
Chicago
to
YWG
Winnipeg
$463

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just found

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Tue, Aug 20 - Sun, Aug 25
ORD
Chicago
to
YWG
Winnipeg
$576

roundtrip

found 5 days ago

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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

Chicago

MDW-Midway Intl.

$430.03

Top Routes from Chicago

Top Routes to Winnipeg

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 Expedia.com, 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.

A verified traveler
Chicago to Winnipeg · United
Sep 2, 2018

Connection of flights were too long

A verified traveler
Chicago to Winnipeg · United
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!!

A verified traveler
Chicago to Winnipeg · United
Jul 3, 2018

Very hard one wheel landing at ORD.

A verified traveler
Chicago to Winnipeg · United
Jun 12, 2018

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

A verified traveler
Chicago to Winnipeg · United
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!!

A verified traveler
Chicago to Winnipeg · United
Nov 24, 2016

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

A verified traveler
Chicago to Winnipeg · United