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$110+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
août 5 — août 121
mar. 8/5
mar. 8/12
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 juillet 31, 2025.

Round-trip from

$195
(oojo)

One-way from

$123
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$641

Good round-trip deal

$448 or less

Good one-way deal

$199 or less
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, 0% potential price rise
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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 July 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 juillet 31, 2025.

This oojo deal was found by Cheapflights users on 7/28. 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.
sam. 9/61:40 pmORD - YWG
1 stop7h 45mWestJet
mer. 9/108:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 7/28$195
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
jeu. 10/25:10 amORD - YWG
1 stop11h 12mMultiple Airlines
sam. 10/48:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 7/31$281
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
mer. 10/89:35 amMDW - YWG
2 stops13h 35mMultiple Airlines
dim. 10/126:30 amYWG - MDW
1 stop9h 54mMultiple Airlines
Deal found 7/29$375
This Gotogate deal was found by Cheapflights users on 7/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/48:40 amORD - YWG
1 stop6h 20mAir Canada
dim. 9/77:00 amYWG - ORD
Nonstop2h 31mAir Canada
Deal found 7/31$403
This Delta deal was found by Cheapflights users on 7/31. 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.
mar. 9/307:15 pmMDW - YWG
1 stop4h 12mDelta
sam. 10/412:44 pmYWG - MDW
1 stop4h 51mDelta
Deal found 7/31$441
This Mytrip deal was found by Cheapflights users on 7/31. 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.
jeu. 9/45:20 pmMDW - YWG
2 stops17h 05mPorter Airlines
dim. 9/711:20 amYWG - MDW
2 stops21h 19mPorter Airlines
Deal found 7/31$478
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/2810:35 amMDW - YWG
1 stop28h 32mWestJet
ven. 11/77:30 amYWG - MDW
1 stop26h 10mWestJet
Deal found 7/31$565

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 juillet 31, 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

sam. 9/6

1:40 pm-9:25 pm

1 stop7h 45m

Winnipeg

mer. 9/10

8:30 am-4:43 pm

1 stop8h 13m

$195

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jeu. 10/2

5:10 am-4:22 pm

1 stop11h 12m

Winnipeg

sam. 10/4

8:30 am-4:43 pm

1 stop8h 13m

$281

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mer. 10/8

9:35 am-11:10 pm

2 stops13h 35m

Winnipeg

dim. 10/12

6:30 am-4:24 pm

1 stop9h 54m

$375

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jeu. 9/4

8:40 am-3:00 pm

1 stop6h 20m

Winnipeg

dim. 9/7

7:00 am-9:31 am

Nonstop2h 31m

$403

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 9/30

7:15 pm-11:27 pm

1 stop4h 12m

Winnipeg

sam. 10/4

12:44 pm-5:35 pm

1 stop4h 51m

$441

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jeu. 9/4

5:20 pm-10:25 am

2 stops17h 05m

Winnipeg

dim. 9/7

11:20 am-8:39 am

2 stops21h 19m

$478

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 10/28

10:35 am-3:07 pm

1 stop28h 32m

Winnipeg

ven. 11/7

7:30 am-9:40 am

1 stop26h 10m

$565

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven. 9/12

5:30 pm-11:26 am

2 stops17h 56m

$110

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jeu. 9/4

6:44 pm-3:55 pm

2 stops21h 11m

$126

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

ven. 9/12

6:20 am-4:22 pm

1 stop10h 02m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 16 results
1
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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 juillet 31, 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 15% 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 juillet 31, 2025.

The most flights from CHI 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 juillet 31, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and United Airlines from Chicago to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,851 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 7 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 $195. Additional round-trip tickets that might be worth considering are offered by Air Canada and United Airlines, with the lowest prices starting at $403 and $416, respectively. These flights start at 64% 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 $123 on WestJet. Other airlines that offer cheap prices include United Airlines from $183 and Air Canada from $188 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 (81%), Air Canada (81%) and United Airlines (81%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $194. On average you can expect to pay $655. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $293.

  • 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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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 juillet 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$542FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$354Average$627FlexibilityNo cancel feeOn-time69%

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