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Winnipeg

$159+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Aug 2 — Aug 91
Sun 8/2
Sun 8/9
1 adult, Economy
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Cheap 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 July 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 10/47:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 6/28$315
This Vliegwinkel 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 10/107:10 pm
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 6/30$335
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.
Sun 10/45:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 10/1011:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 6/30$348
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Tue 11/1011:45 am
ORD
-
YWG
1 stop10h 12m
Porter Airlines
Sun 11/227:00 am
YWG
-
ORD
1 stop10h 30m
Porter Airlines
Deal found 7/2$358
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.
Sun 11/2211:45 am
ORD
-
YWG
1 stop22h 55m
Porter Airlines
Sat 11/287:00 am
YWG
-
ORD
1 stop10h 30m
Porter Airlines
Deal found 6/30$364
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 10/411:15 am
YWG
-
ORD
2 stops10h 20m
Multiple Airlines
Deal found 6/28$372
This Trip.com deal was found by Cheapflights users on 7/1. 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 9/185:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 9/212:55 pm
YWG
-
ORD
1 stop25h 45m
WestJet
Deal found 7/1$375
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/185:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 9/2111:15 am
YWG
-
ORD
2 stops10h 20m
Multiple Airlines
Deal found 7/1$379
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 8/123:15 pm
MDW
-
YWG
1 stop23h 10m
Multiple Airlines
Tue 8/1811:15 am
YWG
-
MDW
2 stops22h 30m
Multiple Airlines
Deal found 7/1$389
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Tue 7/213:20 pm
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
Tue 7/286:05 pm
YWG
-
MDW
1 stop15h 35m
Multiple Airlines
Deal found 7/1$393
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Tue 8/115:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 8/317:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/2$401
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Tue 8/115:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 8/3111:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 7/2$402

Find 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 July 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$315
(Kiwi.com)

One-way from

$159
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$693

Good round-trip deal

$865 or less

Good one-way deal

$337 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
Search Deals
From Chicago (CHI) to Winnipeg
Search Deals
One-way flight from Chicago (CHI) to Winnipeg
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Winnipeg.
Search Deals

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 July 3, 2026.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/21

10:25 am-12:55 am

2 stops14h 30m

Winnipeg

Tue 7/28

6:05 pm-9:40 am

1 stop15h 35m

$526

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/26

8:03 am-3:19 pm

1 stop7h 16m

Winnipeg

Tue 9/29

9:20 am-4:18 pm

1 stop6h 58m

$557

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/6

3:15 pm-10:43 am

2 stops19h 28m

Winnipeg

Mon 8/10

4:15 pm-9:45 am

2 stops17h 30m

$671

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 7/26

7:30 am-9:40 pm

2 stops14h 10m

Winnipeg

Sun 8/2

9:05 pm-4:40 pm

1 stop19h 35m

$672

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/13

7:25 pm-11:30 pm

1 stop4h 05m

Winnipeg

Thu 8/20

4:25 pm-9:17 am

2 stops16h 52m

$693

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 8/10

9:59 am-4:52 pm

1 stop6h 53m

Winnipeg

Fri 8/14

7:00 am-6:01 pm

2 stops11h 01m

$749

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/26

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

Tue 9/29

2:05 pm-7:48 pm

1 stop5h 43m

$770

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 9/19

9:59 am-11:30 pm

1 stop13h 31m

Winnipeg

Tue 9/22

3:58 pm-6:19 pm

1 stop26h 21m

$838

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/13

3:15 pm-5:58 pm

2 stops26h 43m

Winnipeg

Thu 8/20

4:15 pm-9:45 am

2 stops17h 30m

$840

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 7/29

9:19 am-8:20 pm

2 stops11h 01m

Winnipeg

Sun 8/2

4:25 pm-6:33 pm

2 stops26h 08m

$846

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 38 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub the most. FlightHub 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, February is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $62). Flying from Chicago to Winnipeg in January is currently the most expensive (average of $1,074). 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 July 3, 2026.

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 morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% 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 July 3, 2026.

The most flights from CHI to YWG are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Chicago to Winnipeg?

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 July 3, 2026.
Read reviews from past customers who have flown 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.
United Airlines
7.4
Good
9,927 reviews

Comfort

7.3

Food

6.7

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
9,927 reviews
United Airlines
7.4
Good
9,927 reviews

Comfort

7.3

Food

6.7

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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 8 inbound flights from Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • How long is the flight from Chicago to Winnipeg?

    A quick flight from Chicago to Winnipeg can take about 2h 39m. Porter Airlines provides one of the quickest options available for as low as $770. There are 706 mi between Chicago and Winnipeg. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $208. Another option worth looking into is United Airlines, starting at $362 round trip. These flights start at 68% lower than the current average price 3 months from now.

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

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are Atlas Air (100%), SkyWest Airlines (76%) and Air Canada (76%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $337. On average you can expect to pay $732. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $348.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $62). Flying from Chicago to Winnipeg in January is currently the most expensive (average of $1,074). 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

Browse thousands of different options on Cheapflights for your next trip

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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 July 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$208Average$405FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$362Average$748FlexibilityNo cancel feeOn-time69%

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