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$143+ Cheap flights from Chicago (CHI) 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$291
(Justfly.com)

One-way from

$143
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$743

Good round-trip deal

$509 or less

Good one-way deal

$194 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.
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Price to beat on a one-way flight from Chicago (CHI) to Winnipeg.
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Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2025.

This Justfly.com deal was found by Cheapflights users on 4/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/155:30 pmORD - YWG
1 stop15h 33mWestJet
Sun 5/188:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 4/29$291
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Wed 6/255:01 amORD - YWG
1 stop11h 27mMultiple Airlines
Mon 6/309:00 amYWG - ORD
1 stop5h 48mMultiple Airlines
Deal found 4/29$297
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/157:58 pmORD - YWG
Nonstop2h 35mAir Canada
Mon 6/167:00 amYWG - ORD
Nonstop2h 31mAir Canada
Deal found 4/29$480
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 6/66:30 amMDW - YWG
1 stop9h 58mMultiple Airlines
Mon 6/99:00 amYWG - MDW
1 stop9h 02mMultiple Airlines
Deal found 4/29$486
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/102:00 pmMDW - YWG
1 stop6h 15mDelta
Sun 9/146:40 amYWG - MDW
1 stop6h 29mDelta
Deal found 4/29$495
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:10 amORD - YWG
2 stops9h 35mDelta
Tue 6/106:45 amYWG - ORD
2 stops6h 10mDelta
Deal found 4/29$510
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/139:21 amMDW - YWG
1 stop14h 08mWestJet
Fri 6/209:00 amYWG - MDW
1 stop12h 45mWestJet
Deal found 4/29$525
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 6/67:58 pmORD - YWG
Nonstop2h 35mUnited Airlines
Mon 6/92:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 4/29$553
This Flightnetwork deal was found by Cheapflights users on 4/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/109:15 amMDW - YWG
2 stops11h 31mPorter Airlines
Sun 9/1411:45 amYWG - MDW
2 stops28h 39mPorter Airlines
Deal found 4/29$570

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 April 29, 2025.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Chicago

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/15

5:30 pm-9:03 am

1 stop15h 33m

Winnipeg

Sun 5/18

8:30 am-4:44 pm

1 stop8h 14m

$291

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 6/25

5:01 am-4:28 pm

1 stop11h 27m

Winnipeg

Mon 6/30

9:00 am-2:48 pm

1 stop5h 48m

$297

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 6/15

7:58 pm-10:33 pm

Nonstop2h 35m

Winnipeg

Mon 6/16

7:00 am-9:31 am

Nonstop2h 31m

$480

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/6

6:30 am-4:28 pm

1 stop9h 58m

Winnipeg

Mon 6/9

9:00 am-6:02 pm

1 stop9h 02m

$486

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 9/10

2:00 pm-8:15 pm

1 stop6h 15m

Winnipeg

Sun 9/14

6:40 am-1:09 pm

1 stop6h 29m

$495

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/31

7:10 am-4:45 pm

2 stops9h 35m

Winnipeg

Tue 6/10

6:45 am-12:55 pm

2 stops6h 10m

$510

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/13

9:21 am-11:29 pm

1 stop14h 08m

Winnipeg

Fri 6/20

9:00 am-9:45 pm

1 stop12h 45m

$525

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/6

7:58 pm-10:33 pm

Nonstop2h 35m

Winnipeg

Mon 6/9

2:20 pm-4:51 pm

Nonstop2h 31m

$553

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 9/10

9:15 am-8:46 pm

2 stops11h 31m

Winnipeg

Sun 9/14

11:45 am-4:24 pm

2 stops28h 39m

$570

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 8/8

6:20 am-4:23 pm

1 stop10h 03m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 18 results
1
2

Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago 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 to Winnipeg

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in December is currently the most expensive (average of $501). 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 CHI to YWG?

Find hourly flight availability from Chicago 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 April 29, 2025.

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

Weekly flight availability from Chicago to Winnipeg

Explore weekly flight availability from Chicago 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 April 29, 2025.

The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 April 29, 2025.
See what other customers who have flown with Porter Airlines, Delta and United Airlines from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,936 reviews
Porter Airlines
8.0
Very good
285 reviews

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,823 reviews
Porter Airlines
8.0
Very good
285 reviews

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,242 reviews
Porter Airlines
8.0
Very good
285 reviews

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Related info for your journey

Find useful and relevant information for your journey from Chicago 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?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 2 inbound flights from Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $291. Additional round-trip tickets that might be worth considering are offered by Air Canada and Delta, with the lowest prices starting at $480 and $495, respectively. These flights start at 48% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $198 on Porter Airlines. Other airlines that offer cheap prices include WestJet from $199 and Air Canada from $221 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (89%), Air Canada (89%) and United Airlines (89%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $166. On average you can expect to pay $512. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $288.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

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

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago 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 to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in December is currently the most expensive (average of $501). 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

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Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
St. Louis to Winnipeg flights
Midway to Winnipeg flights

Top 2 airlines flying from Chicago to Winnipeg

Discover the top 2 airlines that operate flights from Chicago 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$617FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$429Average$653FlexibilityNo cancel feeOn-time69%

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