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$111+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
juin 17 — juin 241
mar. 6/17
mar. 6/24
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 juin 12, 2025.

Round-trip from

$258
(Kiwi.com)

One-way from

$111
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$566

Good round-trip deal

$552 or less

Good one-way deal

$284 or less
From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 juin 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
mar. 7/810:43 amORD - YWG
2 stops13h 48mMultiple Airlines
ven. 7/119:00 amYWG - ORD
1 stop12h 30mMultiple Airlines
Deal found 6/10$258
This Trip.com deal was found by Cheapflights users on 6/12. 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.
ven. 10/175:30 pmORD - YWG
1 stop28h 00mWestJet
lun. 10/208:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 6/12$287
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
lun. 9/226:15 amMDW - YWG
1 stop10h 07mMultiple Airlines
jeu. 9/259:00 amYWG - MDW
1 stop9h 18mMultiple Airlines
Deal found 6/11$314
This Delta deal was found by Cheapflights users on 6/11. 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.
lun. 9/229:30 amMDW - YWG
2 stops14h 02mDelta
mar. 9/306:40 amYWG - MDW
2 stops15h 04mDelta
Deal found 6/11$404
This Delta deal was found by Cheapflights users on 6/11. 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.
sam. 9/2710:35 amORD - YWG
2 stops12h 57mDelta
mar. 9/306:40 amYWG - ORD
2 stops17h 13mDelta
Deal found 6/11$431
This Air Canada deal was found by Cheapflights users on 6/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/289:50 amORD - YWG
1 stop6h 08mAir Canada
ven. 11/75:15 amYWG - ORD
1 stop5h 43mAir Canada
Deal found 6/11$513
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/189:40 amMDW - YWG
2 stops13h 06mPorter Airlines
dim. 7/206:55 pmYWG - MDW
1 stop13h 50mPorter Airlines
Deal found 6/11$543
This oojo deal was found by Cheapflights users on 6/12. 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.
mar. 10/289:20 amMDW - YWG
2 stops10h 15mWestJet
ven. 11/75:00 amYWG - MDW
2 stops16h 44mWestJet
Deal found 6/12$596

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 juin 12, 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

mar. 7/8

10:43 am-12:31 am

2 stops13h 48m

Winnipeg

ven. 7/11

9:00 am-9:30 pm

1 stop12h 30m

$258

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven. 10/17

5:30 pm-9:30 pm

1 stop28h 00m

Winnipeg

lun. 10/20

8:30 am-4:43 pm

1 stop8h 13m

$287

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

lun. 9/22

6:15 am-4:22 pm

1 stop10h 07m

Winnipeg

jeu. 9/25

9:00 am-6:18 pm

1 stop9h 18m

$314

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

lun. 9/22

9:30 am-11:32 pm

2 stops14h 02m

Winnipeg

mar. 9/30

6:40 am-9:44 pm

2 stops15h 04m

$404

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sam. 9/27

10:35 am-11:32 pm

2 stops12h 57m

Winnipeg

mar. 9/30

6:40 am-11:53 pm

2 stops17h 13m

$431

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mar. 10/28

9:50 am-3:58 pm

1 stop6h 08m

Winnipeg

ven. 11/7

5:15 am-10:58 am

1 stop5h 43m

$513

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

ven. 7/18

9:40 am-10:46 pm

2 stops13h 06m

Winnipeg

dim. 7/20

6:55 pm-8:45 am

1 stop13h 50m

$543

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 10/28

9:20 am-7:35 pm

2 stops10h 15m

Winnipeg

ven. 11/7

5:00 am-9:44 pm

2 stops16h 44m

$596

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mar. 7/8

10:43 am-12:31 am

2 stops13h 48m

$111

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 7/15

11:39 am-12:31 am

2 stops12h 52m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 17 results
1
2

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 $497). 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 juin 12, 2025.

One of the essential ways to save on airfare from Chicago 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 10% on airfare.

What is the cheapest day to fly from Chicago to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago 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 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 juin 12, 2025.

The most flights from CHI to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 juin 12, 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
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,537 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 6 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 $287. Additional round-trip tickets that might be worth considering are offered by Delta and Air Canada, with the lowest prices starting at $404 and $513, respectively. These flights start at 45% 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 $136 on WestJet. Other airlines that offer cheap prices include Delta from $206 and Porter Airlines from $217 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 (78%), Air Canada (78%) and United Airlines (78%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $201. On average you can expect to pay $653. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $247.

  • 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 $497). 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
Midway to Winnipeg flights
St. Louis 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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$601FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$354Average$641FlexibilityNo cancel feeOn-time69%

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