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$148+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 69 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap 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 January 29, 2026.

This FlightHub deal was found by Cheapflights users on 1/27. 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.
Sat 4/256:55 pm
YWG
-
ORD
1 stop21h 45m
WestJet
Thu 4/305:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 1/27$257
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 6/57:00 am
YWG
-
ORD
2 stops9h 40m
WestJet
Tue 6/95:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 1/27$260
This Trip.com deal was found by Cheapflights users on 1/27. 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 3/66:15 am
YWG
-
ORD
1 stop7h 20m
WestJet
Mon 3/92:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
Deal found 1/27$262
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/67:30 am
YWG
-
ORD
1 stop27h 46m
Multiple Airlines
Tue 3/107:41 pm
ORD
-
YWG
2 stops28h 59m
Multiple Airlines
Deal found 1/28$289
This Trip.com deal was found by Cheapflights users on 1/27. 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.
Thu 3/59:00 pm
YWG
-
ORD
1 stop16h 35m
WestJet
Mon 3/92:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
Deal found 1/27$294
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 2/257:30 am
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Wed 3/46:02 pm
ORD
-
YWG
2 stops30h 38m
Multiple Airlines
Deal found 1/28$309
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 6/139:05 pm
YWG
-
ORD
1 stop19h 35m
WestJet
Tue 6/165:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 1/27$318
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/67:30 am
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Tue 3/106:00 am
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Deal found 1/28$320
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 2/257:30 am
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Wed 3/47:15 am
MDW
-
YWG
2 stops17h 25m
Multiple Airlines
Deal found 1/28$348
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/67:30 am
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Mon 3/99:51 pm
MDW
-
YWG
2 stops37h 41m
Multiple Airlines
Deal found 1/27$359
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/137:30 am
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Fri 3/2011:00 am
MDW
-
YWG
2 stops24h 13m
Multiple Airlines
Deal found 1/27$398
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/137:30 am
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Mon 3/301:10 pm
MDW
-
YWG
2 stops11h 29m
Multiple Airlines
Deal found 1/28$409

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(FlightHub)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$477

Good round-trip deal

$338 or less

Good one-way deal

$243 or less
Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.
Search Deals
From Winnipeg to Chicago (CHI)
Search Deals
One-way flight from Winnipeg to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Winnipeg to Chicago (CHI).
Search Deals

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 January 29, 2026.
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

Sat 4/25

6:55 pm-4:40 pm

1 stop21h 45m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-12:55 am

1 stop7h 25m

$257

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/5

7:00 am-4:40 pm

2 stops9h 40m

Chicago O'Hare Intl

Tue 6/9

5:30 pm-12:55 am

1 stop7h 25m

$260

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/6

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-10:40 pm

1 stop8h 20m

$262

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/6

7:30 am-11:16 am

1 stop27h 46m

Chicago O'Hare Intl

Tue 3/10

7:41 pm-3:09 pm

1 stop19h 28m

$291

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 6/13

9:05 pm-4:40 pm

1 stop19h 35m

Chicago O'Hare Intl

Tue 6/16

5:30 pm-12:55 am

1 stop7h 25m

$318

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 2/25

7:30 am-7:07 pm

1 stop11h 37m

Chicago Midway

Wed 3/4

7:15 am-12:40 am

2 stops17h 25m

$348

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/13

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/30

2:20 pm-12:07 pm

2 stops21h 47m

$350

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/13

7:30 am-10:19 pm

1 stop14h 49m

Chicago Midway

Fri 3/20

11:00 am-11:13 am

2 stops24h 13m

$398

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

5:00 am-5:45 pm

2 stops12h 45m

Chicago Midway

Sun 3/8

6:34 pm-7:09 pm

2 stops24h 35m

$453

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 2/25

5:00 am-5:37 pm

2 stops12h 37m

Chicago Midway

Wed 3/4

7:20 pm-7:09 pm

2 stops23h 49m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 30 results
1
2
3
  • 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 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 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 January 23, 2026.

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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $145). Flying from Winnipeg to Chicago in January is currently the most expensive (average of $515). 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 January 29, 2026.

When flying from Winnipeg to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 29, 2026.

The most flights from YWG to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 January 29, 2026.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 3 outbound flights to Chicago per day from 1 airline. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • How long is the flight from Winnipeg to Chicago?

    There are many flights that can get you from Winnipeg to Chicago in 21h 45m. Fly via WestJet to get the fastest option. Airlines will cover a distance of 706 mi.

  • What is the cheapest airline to fly from Winnipeg to Chicago round-trip?

    Our cheapest airline available from Winnipeg to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $199 on this airline. Users have found that United Airlines is 55% cheaper than the other options available to this destination.

  • 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 (77%), Air Canada (77%) or Avianca (77%) 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 $661, our data shows the cheapest flight currently is $197. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $289 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $145). Flying from Winnipeg to Chicago in January is currently the most expensive (average of $515). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 airline flying from Winnipeg to Chicago

Discover the top airline 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$469FlexibilityNo cancel feeOn-time69%

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