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Cheap flights from Winnipeg to Chicago from C$ 173

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 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 69 days in advance, depart on a Wednesday or Friday and return on a Tuesday

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 17 September 2025.

Round-trip from

C$ 268

One-way from

C$ 173

Popular in

April

Cheapest in

September

Average price

C$ 499

Good round-trip deal

C$ 545 or less

Good one-way deal

C$ 583 or less
WestJet
  • WestJet
  • 12/10-19/10
  • 2 total stops
  • 23h 44m total
  • Winnipeg to Chicago
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31/10
  • 31/10
  • 1 total stop
  • 14h 15m total
  • Winnipeg to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 34 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 17 September 2025.

Sun 12/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Sun 19/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 14/9C$ 268
Fri 17/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Sun 19/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 15/9C$ 281
Thu 30/109:00 p.m.YWG - MDW
2 stops21h 39mMultiple Airlines
Thu 6/111:37 p.m.MDW - YWG
1 stop25h 30mMultiple Airlines
Deal found 15/9C$ 300
Fri 3/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Sat 4/101:40 p.m.ORD - YWG
1 stop7h 45mWestJet
Deal found 16/9C$ 300
Sat 11/105:30 p.m.YWG - ORD
1 stop23h 13mWestJet
Sat 18/105:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Deal found 15/9C$ 305
Fri 31/107:30 a.m.YWG - MDW
1 stop11h 09mMultiple Airlines
Sun 2/115:20 a.m.MDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 15/9C$ 318
Thu 16/109:05 p.m.YWG - ORD
1 stop19h 38mWestJet
Sun 19/105:30 p.m.ORD - YWG
1 stop28h 00mWestJet
Deal found 16/9C$ 318
Thu 30/109:00 p.m.YWG - ORD
1 stop16h 35mMultiple Airlines
Thu 6/116:06 p.m.ORD - YWG
2 stops30h 36mMultiple Airlines
Deal found 15/9C$ 362
Mon 27/109:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Thu 20/116:35 p.m.ORD - YWG
1 stop20h 32mMultiple Airlines
Deal found 14/9C$ 377
Fri 17/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
Sun 19/106:20 a.m.MDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 14/9C$ 399
Mon 27/109:00 p.m.YWG - MDW
2 stops14h 38mMultiple Airlines
Thu 20/114:15 p.m.MDW - YWG
1 stop19h 20mMultiple Airlines
Deal found 14/9C$ 461
Thu 16/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
Sun 19/107:50 a.m.MDW - YWG
2 stops16h 50mMultiple Airlines
Deal found 16/9C$ 475

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 629,999 searches. Data last updated 17 September 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 - MDW

YWGMDW

Winnipeg

Thu 30/10

9:00 p.m.-6:39 p.m.

2 stops21h 39m

Chicago Midway

Thu 6/11

1:37 p.m.-3:07 p.m.

1 stop25h 30m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 16/10

6:30 a.m.-4:43 p.m.

2 stops10h 13m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 4/10

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 12/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-2:25 p.m.

2 stops20h 55m

C$ 322

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 31/10

4:10 p.m.-2:57 p.m.

2 stops22h 47m

Chicago Midway

Sun 2/11

5:20 a.m.-2:07 p.m.

1 stop8h 47m

C$ 369

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 27/9

9:10 a.m.-9:58 p.m.

1 stop12h 48m

Chicago O'Hare Intl

Sat 4/10

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 388

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 17/10

9:00 a.m.-11:46 p.m.

1 stop14h 46m

Chicago Midway

Sun 19/10

6:20 a.m.-12:30 a.m.

2 stops18h 10m

C$ 399

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 15/10

9:05 p.m.-4:43 p.m.

1 stop19h 38m

Chicago O'Hare Intl

Wed 22/10

7:43 p.m.-4:25 p.m.

2 stops44h 42m

C$ 403

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 1/11

9:00 p.m.-2:35 p.m.

1 stop17h 35m

Chicago O'Hare Intl

Sat 8/11

6:00 a.m.-12:41 a.m.

2 stops18h 41m

C$ 425

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 16/10

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 19/10

5:01 a.m.-1:09 p.m.

1 stop8h 08m

C$ 469

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 33 results
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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 12 September 2025.

The best time to book flights from Winnipeg to Chicago is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in March is currently the most expensive (average of C$ 348). 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 17 September 2025.

One of the essential ways to save on airfare from Winnipeg to Chicago 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 19% on airfare.

What is the cheapest day to fly from Winnipeg to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Chicago. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 17 September 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 (7 on average).

What’s the top layover airport for flights from Winnipeg to Chicago?

Share of one-stop round-trip flights from Winnipeg to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 63% of one-stop itineraries from Winnipeg to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Chicago?

Average round-trip fare for 1-stop flights from Winnipeg to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 439.

What’s the fastest layover option from Winnipeg to Chicago?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 4h 21m.

Which airport typically offers the quickest layover for flights from Winnipeg to Chicago?

Average layover duration for 1-stop one-way flights from Winnipeg to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 09m.

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 17 September 2025.
Check out reviews from past customers who have flown with United Airlines,WestJet, andAir Canada from Winnipeg to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,926 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
3,095 reviews
United Airlines
7.4
Good
8,926 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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?

    If you book a flight to Chicago from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 7 flights from Winnipeg to Chicago per day from 3 different airlines.

  • How long is the flight from Winnipeg to Chicago?

    Airlines like WestJet fly from Winnipeg to Chicago in about 10h 13m. The time it takes to get you to your destination can typically vary by up to . There are 1136 km between Winnipeg and Chicago.

  • What are the cheapest airlines flying from Winnipeg to Chicago round-trip?

    WestJet, at C$ 199, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Air Canada and United Airlines. WestJet is priced at 67% lower than the current average price of a flight leaving 3 months from now.

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

    Before booking your flight to Chicago from Winnipeg, check out the most reliable airlines to get you to your destination on time: Copa Airlines (85%), SkyWest Airlines (82%), Air Canada( 82%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 224. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 354 on average, our data indicates C$ 1,408 when flying from Winnipeg to Chicago.

  • 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, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in March is currently the most expensive (average of C$ 348). 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

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

Top 3 airlines flying from Winnipeg to Chicago

Discover the top 3 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 629,999 searches. Data last updated 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 199AverageC$ 409FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 321AverageC$ 593FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 484AverageC$ 626FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Winnipeg today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Winnipeg.

Can Cheapflights find flights from Winnipeg to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Winnipeg to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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