ORD - YWG

$154 Find Cheap Flights from Chicago O'Hare Airport to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Winnipeg departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$363
Typical prices: $352-$924
Multiple Airlines
Fri 8/28Tue 9/8
ORD - YWG • 2 stops
Cheapest non-stop
$846
Typical prices: $714-$961
United Airlines
Mon 7/20Thu 7/23
ORD - YWG • Non-stop
Top airlines
Cheapest • from $463 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $443 (round-trip)
Shortest trip • 4h 40m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from O'Hare Intl to Winnipeg (ORD-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Winnipeg

Fri, Aug 28 - Tue, Sep 8
Multiple Airlines Logo
8:40 pm - 3:25 pm
ORD
-
YWG
18h 45m
2 stops
Multiple Airlines Logo
11:15 am - 9:35 pm
YWG
-
ORD
10h 20m
2 stops
$363Multiple Airlines
Fri, Aug 28 - Tue, Sep 8
Multiple Airlines Logo
8:40 pm - 8:25 am
ORD
-
YWG
11h 45m
1 stop
Multiple Airlines Logo
5:10 am - 7:48 pm
YWG
-
ORD
14h 38m
1 stop
$364Multiple Airlines
Fri, Aug 28 - Tue, Sep 8
Multiple Airlines Logo
8:40 pm - 2:05 pm
ORD
-
YWG
17h 25m
2 stops
Multiple Airlines Logo
7:45 am - 8:29 pm
YWG
-
ORD
12h 44m
1 stop
$365Multiple Airlines
Fri, Sep 4 - Mon, Sep 7
Multiple Airlines Logo
3:20 pm - 5:58 pm
ORD
-
YWG
26h 38m
2 stops
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$379Multiple Airlines
Fri, Sep 18 - Sun, Sep 20
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
11:15 am - 9:35 pm
YWG
-
ORD
10h 20m
2 stops
$399Multiple Airlines
Mon, Sep 7 - Wed, Sep 30
Multiple Airlines Logo
8:40 pm - 11:12 am
ORD
-
YWG
14h 32m
1 stop
Multiple Airlines Logo
11:40 am - 9:35 pm
YWG
-
ORD
9h 55m
2 stops
$400Multiple Airlines
Mon, Sep 7 - Wed, Sep 30
Multiple Airlines Logo
8:40 pm - 11:12 am
ORD
-
YWG
14h 32m
1 stop
Multiple Airlines Logo
8:50 pm - 9:00 am
YWG
-
ORD
12h 10m
1 stop
$408Multiple Airlines
Thu, Oct 15 - Wed, Oct 21
Multiple Airlines Logo
5:30 pm - 11:10 am
ORD
-
YWG
17h 40m
1 stop
Multiple Airlines Logo
6:05 pm - 11:00 am
YWG
-
ORD
16h 55m
1 stop
$425Multiple Airlines
Mon, Sep 7 - Wed, Sep 30
Multiple Airlines Logo
5:35 pm - 10:43 am
ORD
-
YWG
17h 08m
2 stops
Multiple Airlines Logo
11:40 am - 9:35 pm
YWG
-
ORD
9h 55m
2 stops
$449Multiple Airlines
Thu, Oct 15 - Wed, Oct 21
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 pm - 2:35 pm
YWG
-
ORD
17h 30m
2 stops
$454Multiple Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Winnipeg flights

Get data-powered insights and trends into flights from O'Hare Intl to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Winnipeg?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Winnipeg departing in August.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Winnipeg?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Winnipeg clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Winnipeg on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago O'Hare Airport to Winnipeg. For your return ticket, we recommend flying on a Saturday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Winnipeg, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are February and May, where the average cost of round-trip tickets is $853 and $785 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Winnipeg?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $876, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from O'Hare Intl to Winnipeg

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada and United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Good to know

Low seasonJune
Cheapest flight$154
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago O'Hare Airport to Winnipeg

When to book flights from O'Hare Intl to Winnipeg

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Winnipeg flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Winnipeg?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was $160 for a one-way ticket and $363 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Winnipeg?

    A passport is required to fly from Chicago O'Hare Airport to Winnipeg.

  • Which airports will I be using when flying from Chicago O'Hare Airport to Winnipeg?

    On your way to Winnipeg, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Winnipeg.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Winnipeg?

    Only American Airlines offers inflight Wi-Fi service on the Chicago O'Hare Airport to Winnipeg flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Winnipeg?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Winnipeg flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Winnipeg?

    Star Alliance is the only airline alliance operating flights between Chicago O'Hare Airport and Winnipeg.

  • On which days can I fly direct from Chicago O'Hare Airport to Winnipeg?

    There are nonstop flights from Chicago O'Hare Airport to Winnipeg on a daily basis.

  • Which is the best airline for flights from Chicago to Winnipeg, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Chicago to Winnipeg are United Airlines and WestJet. With an average price for the route of $748 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of $405 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and YWG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Winnipeg

  • Looking for a cheap flight? 25% of our users found flights on this route for $865 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport to Winnipeg?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Winnipeg.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Winnipeg Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Winnipeg

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Winnipeg to Chicago O'Hare Intl

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airlines flying from O'Hare Intl to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9859 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

2.0 MediocreAnonymous, Jun 2026
ORD - BHM
Read more United Airlines reviews

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

This airline would not refund my money and I had a physician note that I could not fly. They are crooks

Westjet was late and we missed our connecting flight with Cathay. Had to wait 8 hours. Westjet only allows 1 checked in baggage for international flights- it’s always been 2. Canada allows only 1 sandwhich bag size full off small liquids. Everything else will be tossed. Awful trip. Will never fly west jet or go to Toronto to connect flights!

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Flight was good, crew was excellent. No complaints at all

Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

The trip from LAX to Calgary was aboard a 737-700, which is more than twenty years old. Service was fine, and the food was good, but there was no inflight entertainment, and no WiFi. The flight from Calgary to Vancouver was also delayed more than an hour, due to congestion on the Calgary tarmac. And no food service, but there was in-flight WiFi which made a big difference.

Everything you need to know for your flight from O'Hare Intl to Winnipeg

Information on your arrival and departure airports