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$149+ Cheap flights from Winnipeg (YWG) to Chicago (CHI)

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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in June or May, booked 69 days in advance, depart on a Friday or Tuesday and return on a Friday

Cheap flight deals from Winnipeg to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Chicago (CHI). 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 31, 2025.

Round-trip from

$212
(Kiwi.com)

One-way from

$149
(Trip.com)

Popular in

April

Cheapest in

June

Average price

$449

Good round-trip deal

$385 or less

Good one-way deal

$361 or less
From Winnipeg to Chicago (CHI)
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One-way flight from Winnipeg to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 Winnipeg to Chicago (CHI).
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Price to beat on a one-way flight from Winnipeg to Chicago (CHI).
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Find flight deals from Winnipeg to Chicago

Cheapest flights from Winnipeg to Chicago
Explore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Wed 9/248:30 amYWG - ORD
1 stop8h 13mWestJet
Sat 9/271:40 pmORD - YWG
1 stop7h 45mWestJet
Deal found 7/30$212
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/137:00 pmYWG - ORD
2 stops14h 51mMultiple Airlines
Sat 9/201:40 pmORD - YWG
1 stop7h 45mMultiple Airlines
Deal found 7/30$293
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:00 pmYWG - ORD
1 stop8h 11mAir Canada
Fri 9/1910:40 amORD - YWG
1 stop8h 19mAir Canada
Deal found 7/29$324
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Sun 9/211:01 pmORD - YWG
Nonstop2h 30mUnited Airlines
Deal found 7/31$336
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:40 amYWG - MDW
2 stops5h 48mDelta
Sat 9/201:08 pmMDW - YWG
2 stops10h 19mDelta
Deal found 7/30$359
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.
Fri 9/196:30 amYWG - MDW
2 stops26h 10mWestJet
Tue 9/237:15 pmMDW - YWG
1 stop24h 56mWestJet
Deal found 7/31$416
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:55 pmYWG - MDW
1 stop13h 50mMultiple Airlines
Wed 9/35:20 pmMDW - YWG
1 stop16h 21mMultiple Airlines
Deal found 7/30$485

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago 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 31, 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Winnipeg

Fly to

Chicago

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/24

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sat 9/27

1:40 pm-9:25 pm

1 stop7h 45m

$212

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/13

7:00 pm-9:51 am

2 stops14h 51m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$293

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/12

12:00 pm-8:11 pm

1 stop8h 11m

Chicago O'Hare Intl

Fri 9/19

10:40 am-6:59 pm

1 stop8h 19m

$324

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/18

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

1:01 pm-3:31 pm

Nonstop2h 30m

$336

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 9/13

6:40 am-12:28 pm

2 stops5h 48m

Chicago Midway

Sat 9/20

1:08 pm-11:27 pm

2 stops10h 19m

$359

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/19

6:30 am-8:40 am

2 stops26h 10m

Chicago Midway

Tue 9/23

7:15 pm-8:11 pm

1 stop24h 56m

$416

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/27

6:55 pm-8:45 am

1 stop13h 50m

Chicago Midway

Wed 9/3

5:20 pm-9:41 am

1 stop16h 21m

$485

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/9

5:30 pm-4:43 pm

1 stop23h 13m

$149

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/2

8:55 pm-4:43 pm

1 stop19h 48m

$162

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/20

2:20 pm-4:51 pm

Nonstop2h 31m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 16 results
1
2

Best time to book a flight from Winnipeg to Chicago

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

How far ahead should I book a flight from Winnipeg to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Chicago. Price data was last updated on July 25, 2025.

The price you pay for your flight from Winnipeg to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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 YWG to CHI?

Find hourly flight availability from Winnipeg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight at noon.

Weekly flight availability from Winnipeg to Chicago

Explore weekly flight availability from Winnipeg to Chicago. 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 31, 2025.

The most flights from YWG to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 31, 2025.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as Porter Airlines, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

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

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

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

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

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

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

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

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

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

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

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 Winnipeg to Chicago. 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 from for flights from Winnipeg to Chicago?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago. On average, Winnipeg has 7 outbound flights to 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 Winnipeg to Chicago round-trip?

    Our cheapest airline available from Winnipeg to Chicago is WestJet. Our recent data shows that you can find tickets from as low as $212 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $324 and $336 round-trip. Users have found that WestJet is 52% cheaper than the other options available to this destination.

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

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $149. However, be on the lookout for offers from United Airlines and Air Canada, as they are both options that can get you from Winnipeg to Chicago for a low price.

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

    No one likes to see their flight delayed. When booking a flight from Winnipeg to Chicago consider choosing Avianca (93%), SkyWest Airlines (91%) or United Airlines (91%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Winnipeg to Chicago?

    While on average a flight from Winnipeg to Chicago is generally $509, our data shows the cheapest flight currently is $169. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $246 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Chicago 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 Winnipeg to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Winnipeg to Chicago

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

Top 2 airlines flying from Winnipeg to Chicago

Discover the top 2 airlines that operate flights from Winnipeg to Chicago. 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 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$546FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$230Average$645FlexibilityNo cancel feeOn-time67%

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