HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$100+ Cheap flights from O'Hare Intl (ORD) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
jul. 6 — jul. 131
dom. 7/6
dom. 7/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from O'Hare Intl to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated julio 1, 2025.

Round-trip from

$293
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

July

Cheapest in

May

Average price

$670

Good round-trip deal

$641 or less

Good one-way deal

$252 or less
From Chicago O'Hare Intl to Winnipeg
Search Deals
One-way flight from Chicago O'Hare Intl to Winnipeg
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Winnipeg.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Winnipeg.
Search Deals

Find flight deals from O'Hare Intl to Winnipeg

Cheapest flights from O'Hare Intl to Winnipeg
Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/155:01 amORD - YWG
1 stop11h 22mMultiple Airlines
vie. 8/226:00 amYWG - ORD
2 stops17h 54mMultiple Airlines
Deal found 6/30$293
This oojo deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/165:30 pmORD - YWG
1 stop15h 31mWestJet
vie. 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 6/30$309
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/167:54 pmORD - YWG
Nonstop2h 39mUnited Airlines
vie. 10/242:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 6/30$405

Cheapflights Fare Finder

Customize your flight search to find flights from O'Hare Intl to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 1, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.

Fly from

O'Hare Intl

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 8/15

5:01 am-4:23 pm

1 stop11h 22m

Winnipeg

vie. 8/22

6:00 am-11:54 pm

2 stops17h 54m

$293

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/16

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

vie. 10/24

8:30 am-4:43 pm

1 stop8h 13m

$309

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/16

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

vie. 10/24

2:20 pm-4:51 pm

Nonstop2h 31m

$405

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mar. 9/23

11:45 am-12:30 am

2 stops12h 45m

$100

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mar. 9/23

5:30 pm-11:41 am

1 stop18h 11m

$166

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mié. 9/17

1:01 pm-3:31 pm

Nonstop2h 30m

$178

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mar. 8/12

10:40 am-6:59 pm

1 stop8h 19m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Best time to book a flight from O'Hare Intl to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Winnipeg

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of $358). Flying from Chicago O'Hare Intl Airport to Winnipeg in December is currently the most expensive (average of $495). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to YWG?

Find hourly flight availability from O'Hare Intl to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 1, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 12% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Winnipeg. Price data was last updated on June 29, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Winnipeg flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Winnipeg

Explore weekly flight availability from O'Hare Intl to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated julio 1, 2025.

The most flights from ORD to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated julio 1, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and WestJet from Chicago O'Hare Intl Airport to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,852 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,909 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,660 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Winnipeg, you will be flying into Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city. Winnipeg is the only Winnipeg airport and it handles 7 inbound flights from Chicago O'Hare Intl per day. 2 airlines have flights to Winnipeg from Chicago O'Hare Intl on a regular basis.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Winnipeg round-trip?

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Winnipeg round-trip from $309. Another airline that can offer you cheap pricing is United Airlines. These flights start at 40% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Winnipeg one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at $166. United Airlines flights start at $178 while deals on Delta start at $184 one-way.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Winnipeg?

    Consider SkyWest Airlines (86%), Air Canada (86%) or United Airlines (86%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Winnipeg.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Winnipeg?

    On average you can expect to pay $696 for a flight from Chicago O'Hare Intl Airport to Winnipeg. The cheapest flight overall is $194 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $262.

  • Can I find deals for flights from O'Hare Intl to Winnipeg that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Winnipeg.

  • Can I find deals for business class flights from O'Hare Intl to Winnipeg?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of $358). Flying from Chicago O'Hare Intl Airport to Winnipeg in December is currently the most expensive (average of $495). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
Midway to Winnipeg flights

Top 2 airlines flying from O'Hare Intl to Winnipeg

Discover the top 2 airlines that operate flights from O'Hare Intl to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$354Average$641FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.