Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Chicago from C$ 228

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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
2 May — 9 May1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 27 days in advance, depart on a Friday or Wednesday and return on a Monday

Cheap flight deals from Winnipeg to Chicago

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 2 April 2026.

Fri 8/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Mon 11/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 29/3C$ 388
Fri 25/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 27/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 2/4C$ 451
Fri 8/57:00 a.m.
YWG
-
ORD
2 stops9h 40m
WestJet
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 29/3C$ 476
Sun 26/49:05 p.m.
YWG
-
ORD
2 stops14h 27m
Multiple Airlines
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 29/3C$ 481
Tue 12/59:20 a.m.
YWG
-
ORD
1 stop6h 58m
Multiple Airlines
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 30/3C$ 513
Fri 25/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Mon 28/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 31/3C$ 521
Fri 8/57:00 p.m.
YWG
-
MDW
1 stop14h 45m
Multiple Airlines
Mon 11/53:20 p.m.
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
Deal found 29/3C$ 522
Mon 11/56:15 a.m.
YWG
-
ORD
2 stops17h 00m
Multiple Airlines
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 30/3C$ 522
Mon 11/59:05 p.m.
YWG
-
MDW
2 stops14h 07m
Multiple Airlines
Fri 15/53:20 p.m.
MDW
-
YWG
1 stop9h 35m
Multiple Airlines
Deal found 30/3C$ 526
Wed 10/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Thu 18/67:55 a.m.
ORD
-
YWG
2 stops17h 00m
Multiple Airlines
Deal found 30/3C$ 550
Wed 10/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Fri 19/65:15 a.m.
ORD
-
YWG
2 stops19h 40m
Multiple Airlines
Deal found 29/3C$ 551
Tue 21/45:00 a.m.
YWG
-
ORD
2 stops28h 36m
Multiple Airlines
Wed 29/48:58 p.m.
ORD
-
YWG
1 stop27h 42m
Multiple Airlines
Deal found 30/3C$ 554

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 2 April 2026.

Round-trip from

C$ 388

One-way from

C$ 228

Popular in

December

Cheapest in

September

Average price

C$ 654

Good round-trip deal

C$ 544 or less

Good one-way deal

C$ 375 or less
WestJet
  • WestJet
  • 8/5-11/5
  • 2 total stops
  • 17h 05m total
  • Winnipeg to Chicago
Search Deals
4/5
  • 4/5
  • 2 total stops
  • 14h 07m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 629,999 searches. Data last updated 2 April 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 8/5

7:00 p.m.-9:45 a.m.

1 stop14h 45m

Chicago Midway

Mon 11/5

3:20 p.m.-9:45 a.m.

1 stop18h 25m

C$ 522

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 30/4

6:00 a.m.-4:40 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Mon 4/5

7:50 a.m.-11:10 a.m.

2 stops27h 20m

C$ 588

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 1/5

5:20 p.m.-10:14 a.m.

2 stops16h 54m

Chicago Midway

Tue 5/5

5:21 p.m.-4:22 p.m.

2 stops23h 01m

C$ 607

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 30/4

6:00 a.m.-4:40 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Mon 4/5

7:09 p.m.-10:56 a.m.

1 stop15h 47m

C$ 654

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 29/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Tue 2/6

6:24 a.m.-10:54 a.m.

1 stop4h 30m

C$ 654

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 12/5

11:55 a.m.-5:56 p.m.

1 stop6h 01m

Chicago Midway

Fri 15/5

7:13 p.m.-10:54 a.m.

1 stop15h 41m

C$ 702

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 2/5

11:55 a.m.-11:58 p.m.

2 stops12h 03m

Chicago O'Hare Intl

Mon 4/5

6:00 p.m.-10:56 a.m.

2 stops16h 56m

C$ 711

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 29/4

12:00 p.m.-10:23 a.m.

3 stops22h 23m

Chicago O'Hare Intl

Wed 6/5

1:18 p.m.-3:19 p.m.

3 stops26h 01m

C$ 714

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 25/8

12:40 p.m.-6:05 p.m.

1 stop5h 25m

Chicago Midway

Sat 29/8

5:59 p.m.-12:55 a.m.

2 stops30h 56m

C$ 721

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 18/6

5:42 p.m.-6:18 p.m.

1 stop24h 36m

Chicago Midway

Mon 22/6

9:54 a.m.-9:40 p.m.

2 stops11h 46m

C$ 728

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 34 resultsSorted by cheapest first
1
2
3
4

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 13 March 2026.

The best time to book flights from Winnipeg to Chicago is 27 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$ 201). Flying from Winnipeg to Chicago in January is currently the most expensive (average of C$ 715). 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 2 April 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chicago as you normally would.

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 2 April 2026.

The most flights from YWG to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

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

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 80% 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$ 349.

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 06m.

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 08m.

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 2 April 2026.
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
9,533 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

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
9,533 reviews
United Airlines
7.4
Good
9,533 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

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
WestJet
7.2
Good
3,309 reviews
United Airlines
7.4
Good
9,533 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

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
Air Canada
7.1
Good
10,881 reviews
United Airlines
7.4
Good
9,533 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

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?

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

  • How long is the flight from Winnipeg to Chicago?

    Airlines like Delta and WestJet fly from Winnipeg to Chicago in about 10h 40m. The time it takes to get you to your destination can typically vary by up to 6h 14m. There are 1136 km between Winnipeg and Chicago. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    WestJet, at C$ 203, 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 68% 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: Avianca (74%), SkyWest Airlines (74%), Air Canada( 74%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 318. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 593 on average, our data indicates C$ 725 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$ 201). Flying from Winnipeg to Chicago in January is currently the most expensive (average of C$ 715). 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 2 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 203AverageC$ 370FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 319AverageC$ 753FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 489AverageC$ 654FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.