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$88+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jul 31 — Aug 71
From?
To?
Wed 7/31
Wed 8/7
1 adult, Economy
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The best prices from Chicago to Winnipeg are usually found in March or May, booked 42 days in advance, depart on a Saturday or Thursday and return on a Thursday

Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). 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 July 26, 2024.

Popular in

December

Cheapest in

March

Round-trip from

$262
(mytrip.com)

One-way from

$88
(Trip.com)
High demand for flights, 23% potential price rise
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Best time to find cheap flights, 62% potential price drop
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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What is the cheapest day to fly round-trip from Chicago to Winnipeg?

Saturday flights are generally found to be more expensive for flights from Chicago to Winnipeg. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Winnipeg.

How far in advance should I book a flight from Chicago to Winnipeg?

To save up to 491% on this flight, we recommend booking at least 43 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Winnipeg from $610 1-2 weeks out and tickets from $1,097 for flights departing within the next 72 hours.

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

March can be a great time to fly to Winnipeg from Chicago with a flight ticket averaging about $561. Cheapflights users have found deals in the month of March for as cheap as $205. The most expensive prices can be found in the month of December.

What is the cheapest time of day to fly from CHI to YWG?

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 24% on airfare.

Cheap Chicago to Winnipeg flights in July & August 2024

Find cheap flight options from Chicago to Winnipeg specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 26, 2024.
Check out some of the best flight deals from Chicago to Winnipeg in 2024. Check back in a little while for more flight options.
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/179:45 pmORD - YWG
1 stop18h 31mMultiple Airlines
Wed 8/218:00 amYWG - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/25$269
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/179:45 pmORD - YWG
1 stop18h 31mMultiple Airlines
Wed 8/216:00 amYWG - ORD
2 stops17h 17mMultiple Airlines
Deal found 7/25$275
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/246:05 pmORD - YWG
2 stops23h 39mMultiple Airlines
Tue 8/277:45 amYWG - ORD
1 stop11h 03mMultiple Airlines
Deal found 7/24$281
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/246:05 pmORD - YWG
2 stops23h 39mMultiple Airlines
Tue 8/272:40 pmYWG - ORD
2 stops16h 37mMultiple Airlines
Deal found 7/24$286
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/246:05 pmORD - YWG
2 stops23h 39mMultiple Airlines
Tue 8/276:30 amYWG - ORD
3 stops23h 51mMultiple Airlines
Deal found 7/24$288
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/247:55 amORD - YWG
3 stops33h 49mMultiple Airlines
Tue 8/272:05 pmYWG - ORD
3 stops16h 16mMultiple Airlines
Deal found 7/24$295
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/246:05 pmORD - YWG
2 stops29h 53mMultiple Airlines
Tue 8/277:45 amYWG - ORD
1 stop11h 03mMultiple Airlines
Deal found 7/24$304
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/246:05 pmORD - YWG
2 stops29h 53mMultiple Airlines
Tue 8/272:40 pmYWG - ORD
2 stops16h 37mMultiple Airlines
Deal found 7/24$309
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1710:57 pmORD - YWG
3 stops25h 31mMultiple Airlines
Wed 8/218:00 amYWG - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/25$310

Chicago to Winnipeg 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Winnipeg in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
Check out some of the best flight deals from Chicago to Winnipeg in 2024. Check back in a little while for more flight options.
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/186:39 pmORD - YWG
3 stops25h 24mMultiple Airlines
Sun 9/228:00 amYWG - ORD
1 stop15h 50mMultiple Airlines
Deal found 7/25$262
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/179:45 pmORD - YWG
1 stop18h 31mMultiple Airlines
Wed 8/218:00 amYWG - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/25$269
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 9/207:30 amMDW - YWG
1 stop8h 00mMultiple Airlines
Sun 9/228:00 amYWG - MDW
1 stop9h 45mMultiple Airlines
Deal found 7/24$274
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/186:39 pmORD - YWG
3 stops25h 24mMultiple Airlines
Sun 9/226:50 amYWG - ORD
2 stops17h 00mMultiple Airlines
Deal found 7/25$275
This mytrip.com deal was found by Cheapflights users on 7/23. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/107:40 amORD - YWG
3 stops31h 47mMultiple Airlines
Thu 9/128:00 amYWG - ORD
1 stop15h 50mMultiple Airlines
Deal found 7/23$279
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/246:05 pmORD - YWG
2 stops23h 39mMultiple Airlines
Tue 8/277:45 amYWG - ORD
1 stop11h 03mMultiple Airlines
Deal found 7/24$281
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/146:39 pmORD - YWG
3 stops27h 39mMultiple Airlines
Mon 9/162:05 pmYWG - ORD
3 stops17h 46mMultiple Airlines
Deal found 7/24$282
This mytrip.com deal was found by Cheapflights users on 7/23. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/106:30 amORD - YWG
1 stop9h 46mMultiple Airlines
Thu 9/128:00 amYWG - ORD
1 stop15h 50mMultiple Airlines
Deal found 7/23$283
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/146:39 pmORD - YWG
3 stops25h 24mMultiple Airlines
Mon 9/168:00 amYWG - ORD
2 stops22h 07mMultiple Airlines
Deal found 7/24$285

Chicago to Winnipeg flights leaving soon

Find last-minute flight options from Chicago to Winnipeg for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
Have a look at some of the flights available from Chicago to Winnipeg departing last-minute. Users should be sure to double check the price, date, and time of their last-minute flight.
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/26:15 amMDW - YWG
2 stops15h 58mMultiple Airlines
Sun 8/45:15 pmYWG - MDW
1 stop11h 30mMultiple Airlines
Deal found 7/24$586
This Air Canada deal was found by Cheapflights users on 7/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/32:15 pmORD - YWG
1 stop6h 42mAir Canada
Sat 8/1012:20 pmYWG - ORD
1 stop8h 24mAir Canada
Deal found 7/25$699
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/309:18 amMDW - YWG
2 stops23h 44mMultiple Airlines
Tue 8/66:00 amYWG - MDW
2 stops15h 37mMultiple Airlines
Deal found 7/25$700
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/305:15 pmMDW - YWG
3 stops24h 37mPorter Airlines
Tue 8/66:00 amYWG - MDW
2 stops15h 37mPorter Airlines
Deal found 7/25$702
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/26:00 amMDW - YWG
1 stop9h 22mMultiple Airlines
Sun 8/45:15 pmYWG - MDW
1 stop11h 30mMultiple Airlines
Deal found 7/24$711
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/29:18 amMDW - YWG
2 stops12h 44mMultiple Airlines
Sun 8/46:00 amYWG - MDW
2 stops10h 17mMultiple Airlines
Deal found 7/24$718
This JustFly deal was found by Cheapflights users on 7/25. 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 JustFly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/35:15 pmORD - YWG
1 stop6h 16mWestJet
Sat 8/107:30 amYWG - ORD
2 stops12h 18mWestJet
Deal found 7/25$771
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/305:15 pmMDW - YWG
3 stops24h 37mMultiple Airlines
Tue 8/68:50 pmYWG - MDW
3 stops24h 47mMultiple Airlines
Deal found 7/25$794
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/25:15 pmMDW - YWG
3 stops24h 37mPorter Airlines
Sun 8/46:00 amYWG - MDW
2 stops10h 17mPorter Airlines
Deal found 7/24$823

One-way flights to Winnipeg from Chicago

Search for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Winnipeg. Those seeking round-trip flights from Chicago to Winnipeg should utilize the search form at the the top of the page.
This Trip.com deal was found by Cheapflights users on 7/24. 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.
Sun 9/86:00 amMDW - YWG
1 stop9h 27mMultiple Airlines
Deal found 7/24$88
This Trip.com deal was found by Cheapflights users on 7/24. 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.
Sun 9/86:05 amORD - YWG
1 stop9h 22mMultiple Airlines
Deal found 7/24$89
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Thu 8/156:50 pmORD - YWG
1 stop20h 32mMultiple Airlines
Deal found 7/24$105
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Thu 8/156:50 pmORD - YWG
1 stop20h 32mMultiple Airlines
Deal found 7/25$106
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/87:24 pmORD - YWG
2 stops20h 03mMultiple Airlines
Deal found 7/24$118
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/156:05 pmORD - YWG
2 stops23h 39mMultiple Airlines
Deal found 7/24$123
This mytrip.com deal was found by Cheapflights users on 7/24. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/87:40 amORD - YWG
3 stops31h 47mMultiple Airlines
Deal found 7/24$148
This mytrip.com deal was found by Cheapflights users on 7/25. 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1410:57 pmORD - YWG
3 stops23h 46mMultiple Airlines
Deal found 7/25$154
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Thu 8/158:42 pmORD - YWG
2 stops18h 40mMultiple Airlines
Deal found 7/25$156

Find flights from Chicago to Winnipeg within your budget

Customize your flight search to find flights from Chicago to Winnipeg 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 2,752,877 searches. Data last updated July 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$262 - $567

Route

Depart

Return

Price

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/18

3 stops25h 24m

Winnipeg

Sun 9/22

1 stop15h 50m

$262

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 8/17

1 stop18h 31m

Winnipeg

Wed 8/21

1 stop15h 17m

$269

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/18

3 stops25h 24m

Winnipeg

Sun 9/22

2 stops17h 00m

$275

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/14

3 stops25h 24m

Winnipeg

Mon 9/16

1 stop15h 50m

$279

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/14

1 stop6h 08m

Winnipeg

Mon 9/16

Nonstop2h 32m

$392

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 9/20

2 stops9h 52m

Winnipeg

Sun 9/22

2 stops10h 17m

$400

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/28

1 stop6h 35m

Winnipeg

Tue 10/1

1 stop6h 20m

$435

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 9/28

1 stop5h 31m

Winnipeg

Tue 10/1

2 stops10h 09m

$459

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 8/23

1 stop26h 03m

Winnipeg

Fri 8/30

2 stops10h 27m

$567

Flights are sorted by cheapest first

Deals found on 7/25

How far ahead should I book a flight from Chicago to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Winnipeg. Price data was last updated on July 23, 2024.
The price you pay for your flight from Chicago to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 42 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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What is the cheapest day to fly from Chicago to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on July 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago 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.

Temperature and rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature and rainfall totals by month.

YWG

Temperature

3.2 - 68 °F

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated July 26, 2024.
See what other customers who have flown with Porter Airlines, United Airlines and Air Canada from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
9,630 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Porter Airlines
7.6
Good
344 reviews
Delta
8.0
Very good
9,630 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

United Airlines
7.4
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

WestJet
7.4
Good
2,761 reviews
Delta
8.0
Very good
9,630 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Air Canada
6.9
Okay
7,353 reviews
Delta
8.0
Very good
9,630 reviews

Food

7.4

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. 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 into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 0 inbound flights from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find flights from Chicago to Winnipeg for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago to Winnipeg for under $300. The cheapest flight booked recently is on Multiple Airlines for just $262, but on average you can expect to pay $300.

  • Are there nonstop flights from Chicago to Winnipeg for under $500 on Cheapflights?

    Cheapflights has at least 16 direct flights from Chicago to Winnipeg under $500. A good price for a nonstop flight from Chicago to Winnipeg is less than $667.

  • Are there last-minute flights available from Chicago to Winnipeg for under $600?

    There are currently 17+ open flights from Chicago to Winnipeg within the next 7 days for less than $600.

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

    Flying on United Airlines is currently your cheapest option to Winnipeg, with prices starting at $392. This flight start at 30% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $177 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $205 and United Airlines from $219 one-way.

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

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (85%), Air Canada (85%) and United Airlines (85%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $249. On average you can expect to pay $456. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $195.

  • What does ORD to YWG mean?

    Chicago O'Hare Intl Airport is ORD and Winnipeg Airport is YWG. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Winnipeg that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Winnipeg flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Winnipeg with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Winnipeg flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Winnipeg that allow pets onboard?

    Many airlines flying from Chicago to Winnipeg offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Winnipeg?

    Yes, you can often find last-minute deals on Chicago to Winnipeg flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Winnipeg flight deals updated?

    The Chicago to Winnipeg flight deals you see on this page were last updated on 7/25.

  • What are the most popular airlines that fly from Chicago to Winnipeg?

    Before booking your flight from Chicago to Winnipeg check out the most popular airlines for this route: Air Canada, Delta or United Airlines.

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $388). Flying from Chicago to Winnipeg in August is currently the most expensive (average of $528). 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.

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Alternative routes for Chicago to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Winnipeg flights
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Top 3 airlines flying from Chicago to Winnipeg

Discover the top 3 airlines that operate flights from Chicago to Winnipeg. 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 2,752,877 searches. Data last updated July 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$163Average$562FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$373Average$749FlexibilityNo cancel feeOn-time69%
DeltaCheapest$462Average$614FlexibilityNo cancel feeOn-timeN/A
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Search flights from Chicago to Winnipeg by cabin class

Find flights from Chicago to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Chicago to Winnipeg

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 26, 2024.
0%of flight departuresEarly morningMidnight to 6 am
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100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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