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Cheap flights from Winnipeg to Chicago from C$ 269

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 31/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
31 Jul — 7 Aug1
1 adult
1 adult, Economy, 0 bags

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 1 July 2026.

Mon 19/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 22/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 30/6C$ 398
Thu 24/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 27/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 27/6C$ 425
Fri 25/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 1/105:30 p.m.
ORD
-
YWG
1 stop23h 55m
WestJet
Deal found 27/6C$ 455
Fri 4/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 6/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 27/6C$ 475
Fri 30/106:15 a.m.
YWG
-
ORD
1 stop7h 20m
WestJet
Sun 1/112:20 p.m.
ORD
-
YWG
1 stop7h 20m
WestJet
Deal found 27/6C$ 476
Wed 26/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 28/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 29/6C$ 496
Mon 12/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 15/105:30 p.m.
ORD
-
YWG
1 stop17h 40m
WestJet
Deal found 27/6C$ 499
Mon 19/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Thu 22/107:00 a.m.
ORD
-
YWG
2 stops10h 58m
Multiple Airlines
Deal found 30/6C$ 503
Wed 2/97:10 p.m.
YWG
-
ORD
1 stop21h 30m
WestJet
Sun 6/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 29/6C$ 506
Mon 12/1011:15 a.m.
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Thu 15/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 27/6C$ 554
Fri 7/84:25 p.m.
YWG
-
MDW
1 stop17h 15m
Multiple Airlines
Sun 9/83:15 p.m.
MDW
-
YWG
1 stop23h 10m
Multiple Airlines
Deal found 28/6C$ 556
Tue 4/86:15 a.m.
YWG
-
MDW
1 stop27h 30m
Multiple Airlines
Fri 14/83:15 p.m.
MDW
-
YWG
2 stops26h 43m
Multiple Airlines
Deal found 29/6C$ 560

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 1 July 2026.

Round-trip from

C$ 398

One-way from

C$ 269

Popular in

January

Cheapest in

September

Average price

C$ 870

Good round-trip deal

C$ 775 or less

Good one-way deal

C$ 607 or less
WestJet
  • WestJet
  • 19/10-22/10
  • 2 total stops
  • 17h 05m total
  • Winnipeg to Chicago
Search Deals
WestJet
  • WestJet
  • 31/8
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 201 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 67 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 1 July 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 - ORD

YWGORD

Winnipeg

Thu 30/7

7:45 a.m.-2:55 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Sun 2/8

8:40 p.m.-8:25 a.m.

1 stop11h 45m

C$ 620

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Sat 12/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

C$ 663

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 22/8

7:00 a.m.-5:41 p.m.

2 stops10h 41m

Chicago O'Hare Intl

Sat 29/8

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 692

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 13/10

6:35 a.m.-9:34 p.m.

1 stop14h 59m

Chicago O'Hare Intl

Sun 18/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 726

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 15/9

5:44 p.m.-9:07 a.m.

2 stops15h 23m

Chicago Midway

Sat 19/9

4:30 p.m.-3:08 p.m.

2 stops22h 38m

C$ 732

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 30/7

6:15 a.m.-2:35 p.m.

1 stop8h 20m

Chicago Midway

Sun 2/8

10:20 a.m.-7:40 p.m.

1 stop9h 20m

C$ 769

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 13/10

9:05 p.m.-9:52 a.m.

2 stops12h 47m

Chicago Midway

Sun 18/10

1:00 p.m.-12:55 a.m.

2 stops11h 55m

C$ 837

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 21/9

6:40 a.m.-1:20 p.m.

1 stop6h 40m

Chicago Midway

Tue 22/9

7:01 p.m.-3:08 p.m.

2 stops20h 07m

C$ 859

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 15/7

7:45 a.m.-6:25 p.m.

2 stops10h 40m

Chicago Midway

Tue 21/7

1:18 p.m.-12:55 a.m.

2 stops11h 37m

C$ 874

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 15/7

6:15 a.m.-4:15 p.m.

2 stops10h 00m

Chicago Midway

Wed 22/7

1:18 p.m.-12:55 a.m.

2 stops11h 37m

C$ 874

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/6

Showing 1-10 of 35 resultsSorted by cheapest first
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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

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

Currently, November is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 181). Flying from Winnipeg to Chicago in January is currently the most expensive (average of C$ 636). 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 1 July 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 1 July 2026.

The most flights from YWG to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 83% 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$ 373.

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 04m.

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 1 July 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
9,906 reviews
Check prices

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

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
9,906 reviews
United Airlines
7.4
Good
9,906 reviews
Check prices

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

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
3,390 reviews
United Airlines
7.4
Good
9,906 reviews
Check prices

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

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
11,279 reviews
United Airlines
7.4
Good
9,906 reviews
Check prices

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

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

  • How long is the flight from Winnipeg to Chicago?

    Airlines like Porter Airlines, WestJet, and Delta fly from Winnipeg to Chicago in about 6h 58m. The time it takes to get you to your destination can typically vary by up to 8h 25m. 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$ 278, 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: Copa Airlines (87%), Avianca (84%), Air New Zealand( 83%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 391. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 503 on average, our data indicates C$ 1,002 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, November is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 181). Flying from Winnipeg to Chicago in January is currently the most expensive (average of C$ 636). 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 1 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 278AverageC$ 423FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 375AverageC$ 816FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 500AverageC$ 910FlexibilityNo 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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