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Cheap flights from Winnipeg to Chicago from C$ 182

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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

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 Monday

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Enter your travel dates to find the best prices.

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 30 October 2025.

Fri 5/127:30 a.m.YWG - ORD
1 stop28h 24mMultiple Airlines
Sun 7/1210:24 a.m.ORD - YWG
2 stops14h 17mMultiple Airlines
Deal found 29/10C$ 276
Wed 26/117:30 a.m.YWG - ORD
1 stop16h 38mMultiple Airlines
Wed 3/128:00 a.m.ORD - YWG
2 stops16h 41mMultiple Airlines
Deal found 29/10C$ 297
Thu 4/129:00 p.m.YWG - MDW
2 stops25h 12mMultiple Airlines
Sun 7/126:15 a.m.MDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 29/10C$ 299
Tue 11/119:00 p.m.YWG - MDW
2 stops15h 41mMultiple Airlines
Tue 18/111:56 p.m.MDW - YWG
1 stop25h 11mMultiple Airlines
Deal found 29/10C$ 300
Tue 11/119:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Tue 18/1112:37 p.m.ORD - YWG
1 stop26h 30mMultiple Airlines
Deal found 29/10C$ 300
Thu 4/129:00 p.m.YWG - ORD
2 stops17h 40mMultiple Airlines
Sun 7/126:11 a.m.ORD - YWG
1 stop8h 56mMultiple Airlines
Deal found 29/10C$ 341
Fri 5/127:30 a.m.YWG - ORD
1 stop28h 24mMultiple Airlines
Mon 8/129:27 p.m.ORD - YWG
2 stops27h 12mMultiple Airlines
Deal found 28/10C$ 350
Sat 15/119:00 p.m.YWG - ORD
2 stops27h 11mMultiple Airlines
Sat 13/121:24 p.m.ORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 28/10C$ 371
Fri 28/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Fri 5/128:42 p.m.MDW - YWG
2 stops27h 59mMultiple Airlines
Deal found 29/10C$ 383
Fri 21/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Tue 25/116:05 a.m.MDW - YWG
2 stops18h 36mMultiple Airlines
Deal found 29/10C$ 398
Fri 21/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Sun 23/116:05 a.m.MDW - YWG
1 stop9h 02mMultiple Airlines
Deal found 30/10C$ 465
Wed 26/117:30 a.m.YWG - MDW
1 stop15h 13mMultiple Airlines
Wed 3/1211:00 a.m.MDW - YWG
1 stop13h 42mMultiple Airlines
Deal found 29/10C$ 503

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 30 October 2025.

Round-trip from

C$ 274

One-way from

C$ 182

Popular in

April

Cheapest in

September

Average price

C$ 521

Good round-trip deal

C$ 613 or less

Good one-way deal

C$ 282 or less
5/12-8/12
  • 5/12-8/12
  • 3 total stops
  • 36h 06m total
  • Winnipeg to Chicago
Search Deals
26/11
  • 26/11
  • 1 total stop
  • 15h 13m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 629,999 searches. Data last updated 30 October 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

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Sun 7/12

6:11 a.m.-3:07 p.m.

1 stop8h 56m

C$ 282

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Wed 3/12

8:00 a.m.-12:41 a.m.

2 stops16h 41m

C$ 297

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/12

9:00 p.m.-10:12 p.m.

2 stops25h 12m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 299

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 11/11

9:00 p.m.-12:41 p.m.

2 stops15h 41m

Chicago Midway

Tue 18/11

1:56 p.m.-3:07 p.m.

1 stop25h 11m

C$ 332

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Mon 8/12

7:10 a.m.-6:03 p.m.

1 stop10h 53m

C$ 369

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 28/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

Chicago Midway

Fri 5/12

8:42 p.m.-12:41 a.m.

2 stops27h 59m

C$ 383

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 21/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

Chicago Midway

Tue 25/11

6:05 a.m.-12:41 a.m.

2 stops18h 36m

C$ 398

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Tue 25/11

11:48 a.m.-3:07 p.m.

2 stops27h 19m

C$ 447

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

9:00 p.m.-8:27 p.m.

3 stops23h 27m

Chicago O'Hare Intl

Thu 13/11

10:52 a.m.-8:06 p.m.

3 stops33h 14m

C$ 473

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Fri 19/12

1:27 p.m.-1:23 a.m.

1 stop11h 56m

C$ 489

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

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 24 October 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 202). Flying from Winnipeg to Chicago in March is currently the most expensive (average of C$ 554). 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 30 October 2025.

One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.

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

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 30 October 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
8,998 reviews
Check prices

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,152 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,381 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 2 flights from Winnipeg to Chicago per day from 3 different airlines.

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

    WestJet, at C$ 202, 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 66% 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: SkyWest Airlines (85%), Air Canada (85%), United Airlines( 85%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 196. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 257 on average, our data indicates C$ 893 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 202). Flying from Winnipeg to Chicago in March is currently the most expensive (average of C$ 554). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 202AverageC$ 463FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 365AverageC$ 635FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 491AverageC$ 639FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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

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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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