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$159+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
may. 5 — may. 121
lun. 5/5
lun. 5/12
1 adult, Economy
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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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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 Wednesday or Friday and return on a Saturday

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 abril 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$279
(Mytrip)

One-way from

$174
(Trip.com)

Popular in

August

Cheapest in

June

Average price

$497

Good round-trip deal

$521 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.
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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. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 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 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 abril 30, 2025.

This Trip.com deal was found by Cheapflights users on 4/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/98:30 amYWG - ORD
1 stop8h 14mWestJet
mar. 6/105:30 pmORD - YWG
1 stop21h 00mWestJet
Deal found 4/28$261
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
lun. 7/149:00 amYWG - ORD
1 stop8h 11mMultiple Airlines
jue. 7/176:00 amORD - YWG
2 stops13h 51mMultiple Airlines
Deal found 4/28$313
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.
jue. 6/56:30 amYWG - MDW
2 stops16h 48mMultiple Airlines
lun. 6/96:30 amMDW - YWG
1 stop9h 58mMultiple Airlines
Deal found 4/29$366
This Air Canada deal was found by Cheapflights users on 4/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/52:20 pmYWG - ORD
Nonstop2h 31mAir Canada
dom. 6/87:58 pmORD - YWG
Nonstop2h 35mAir Canada
Deal found 4/28$404
This CheapTicketsDeal 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/55:35 pmYWG - MDW
1 stop24h 10mWestJet
lun. 6/97:21 pmMDW - YWG
1 stop24h 51mWestJet
Deal found 4/29$424
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/126:45 amYWG - MDW
2 stops14h 56mDelta
jue. 7/171:09 pmMDW - YWG
2 stops10h 16mDelta
Deal found 4/28$430
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/91:40 pmYWG - ORD
1 stop5h 50mUnited Airlines
mar. 6/101:02 pmORD - YWG
Nonstop2h 29mUnited Airlines
Deal found 4/28$432
This Lucky2Go 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/296:55 pmYWG - MDW
1 stop21h 59mPorter Airlines
dom. 6/19:40 amMDW - YWG
1 stop26h 45mPorter Airlines
Deal found 4/29$445
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/128:35 amYWG - ORD
1 stop8h 15mDelta
jue. 7/176:00 amORD - YWG
1 stop5h 31mDelta
Deal found 4/28$455

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 abril 30, 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

lun. 6/9

8:30 am-4:44 pm

1 stop8h 14m

Chicago O'Hare Intl

mar. 6/10

5:30 pm-2:30 pm

1 stop21h 00m

$261

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

lun. 7/14

9:00 am-5:11 pm

1 stop8h 11m

Chicago O'Hare Intl

jue. 7/17

6:00 am-7:51 pm

2 stops13h 51m

$313

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 6/5

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

dom. 6/8

7:58 pm-10:33 pm

Nonstop2h 35m

$404

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sáb. 7/12

6:45 am-9:41 pm

2 stops14h 56m

Chicago Midway

jue. 7/17

1:09 pm-11:25 pm

2 stops10h 16m

$430

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

lun. 6/9

1:40 pm-7:30 pm

1 stop5h 50m

Chicago O'Hare Intl

mar. 6/10

1:02 pm-3:31 pm

Nonstop2h 29m

$432

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

jue. 5/29

6:55 pm-4:54 pm

1 stop21h 59m

Chicago Midway

dom. 6/1

9:40 am-12:25 pm

1 stop26h 45m

$445

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mar. 5/27

6:40 am-1:15 pm

1 stop6h 35m

Chicago Midway

mié. 5/28

9:20 am-4:45 pm

1 stop7h 25m

$453

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 7/12

8:35 am-4:50 pm

1 stop8h 15m

Chicago O'Hare Intl

jue. 7/17

6:00 am-11:31 am

1 stop5h 31m

$455

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mié. 7/30

8:15 am-5:39 pm

1 stop9h 24m

Chicago Midway

lun. 8/4

5:20 pm-10:46 pm

2 stops29h 26m

$566

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

lun. 7/7

9:00 am-4:55 pm

1 stop7h 55m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 18 results
1
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Compare providers for flights from Winnipeg to Chicago

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 Winnipeg to Chicago in April.
ProviderPrice AccuracyTrust Score*
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 Winnipeg-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Chicago 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 Winnipeg-Chicago 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 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 April 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 abril 30, 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 35% on your trip compared to booking a flight in the morning.

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 abril 30, 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
285 reviews

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.8

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

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.8

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

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.8

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

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.8

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

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.8

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

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.8

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 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 1 outbound flight 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 $279 on this airline. Additional options worth looking into are Air Canada and Delta, starting at $418 and $430 round-trip. Users have found that WestJet is 39% 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 Porter Airlines, with whom users have recently found tickets for as low as $201. However, be on the lookout for offers from Air Canada and Delta, 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 SkyWest Airlines (79%), Air Canada (79%) or United Airlines (79%) 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 $497, our data shows the cheapest flight currently is $125. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $264 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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 abril 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$572FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$443Average$547FlexibilityNo cancel feeOn-time69%

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