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Cheap flights from Winnipeg to Chicago from C$ 208

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 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
4 mai — 11 mai1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in June or May, booked 69 days in advance, depart on a Wednesday or Tuesday 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 29 avril 2025.

Round-trip from

C$ 406

One-way from

C$ 208

Popular in

August

Cheapest in

June

Average price

C$ 689

Good round-trip deal

C$ 572 or less

Good one-way deal

C$ 194 or less
15/7-17/7
  • 15/7-17/7
  • 3 total stops
  • 21h 29m total
  • Winnipeg to Chicago
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20/5
  • 20/5
  • 1 total stop
  • 7h 41m total
  • Winnipeg to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 65 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 29 avril 2025.

mar. 15/79:00 a.m.YWG - ORD
1 stop7h 38mMultiple Airlines
jeu. 17/76:00 a.m.ORD - YWG
2 stops13h 51mMultiple Airlines
Deal found 27/4C$ 406
ven. 5/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
ven. 17/105:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Deal found 26/4C$ 421
jeu. 5/62:20 p.m.YWG - ORD
Nonstop2h 31mAir Canada
dim. 8/67:58 p.m.ORD - YWG
Nonstop2h 35mAir Canada
Deal found 27/4C$ 560
ven. 18/77:00 a.m.YWG - ORD
Nonstop2h 31mUnited Airlines
sam. 19/79:32 p.m.ORD - YWG
1 stop15h 37mUnited Airlines
Deal found 27/4C$ 575
jeu. 5/66:40 a.m.YWG - ORD
2 stops9h 50mDelta
dim. 8/66:00 a.m.ORD - YWG
1 stop5h 36mDelta
Deal found 27/4C$ 588
sam. 12/76:45 a.m.YWG - MDW
2 stops14h 56mDelta
jeu. 17/71:09 p.m.MDW - YWG
2 stops10h 16mDelta
Deal found 28/4C$ 596
jeu. 12/68:35 a.m.YWG - MDW
1 stop9h 05mWestJet
jeu. 19/69:21 a.m.MDW - YWG
1 stop7h 31mWestJet
Deal found 28/4C$ 617
lun. 9/611:45 a.m.YWG - MDW
2 stops21h 00mPorter Airlines
mar. 10/65:20 p.m.MDW - YWG
2 stops29h 26mPorter Airlines
Deal found 28/4C$ 768
mer. 30/78:15 a.m.YWG - MDW
1 stop9h 24mMultiple Airlines
lun. 4/85:20 p.m.MDW - YWG
2 stops29h 26mMultiple Airlines
Deal found 28/4C$ 784

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 29 avril 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

mar. 15/7

9:00 a.m.-4:38 p.m.

1 stop7h 38m

Chicago O'Hare Intl

jeu. 17/7

6:00 a.m.-7:51 p.m.

2 stops13h 51m

C$ 406

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mer. 11/6

8:30 a.m.-4:44 p.m.

1 stop8h 14m

Chicago O'Hare Intl

mer. 18/6

6:00 a.m.-4:52 p.m.

1 stop10h 52m

C$ 491

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jeu. 5/6

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

dim. 8/6

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

C$ 560

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

ven. 18/7

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

Nonstop2h 31m

Chicago O'Hare Intl

sam. 19/7

9:32 p.m.-1:09 p.m.

1 stop15h 37m

C$ 575

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jeu. 5/6

12:52 p.m.-9:30 p.m.

1 stop8h 38m

Chicago O'Hare Intl

dim. 8/6

6:00 a.m.-11:36 a.m.

1 stop5h 36m

C$ 588

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sam. 12/7

6:45 a.m.-9:41 p.m.

2 stops14h 56m

Chicago Midway

jeu. 17/7

1:46 p.m.-8:10 p.m.

1 stop6h 24m

C$ 596

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

jeu. 12/6

8:35 a.m.-5:40 p.m.

1 stop9h 05m

Chicago Midway

jeu. 19/6

9:21 a.m.-4:52 p.m.

1 stop7h 31m

C$ 617

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

lun. 9/6

11:45 a.m.-8:45 a.m.

2 stops21h 00m

Chicago Midway

mar. 10/6

5:20 p.m.-10:46 p.m.

2 stops29h 26m

C$ 768

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mer. 30/7

8:15 a.m.-5:39 p.m.

1 stop9h 24m

Chicago Midway

lun. 4/8

5:20 p.m.-10:46 p.m.

2 stops29h 26m

C$ 784

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mar. 20/5

9:00 a.m.-4:41 p.m.

1 stop7h 41m

C$ 208

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 17 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 25 April 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$ 355). 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 29 avril 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 morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 21% 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. Monday 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 29 avril 2025.

The most flights from YWG to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 29 avril 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and United Airlines from Winnipeg to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Crew

8.8

Entertainment

7.0

Overall

8.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Crew

8.8

Entertainment

7.0

Overall

8.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Crew

8.8

Entertainment

7.0

Overall

8.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Crew

8.8

Entertainment

7.0

Overall

8.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,823 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Crew

8.8

Entertainment

7.0

Overall

8.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,240 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Crew

8.8

Entertainment

7.0

Overall

8.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 3 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$ 421, 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 34% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 305. However, be on the lookout for offers from WestJet and Air Canada, as they are both options that can get you from Winnipeg to Chicago for a low price.

  • 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 (79%), Air Canada (79%), United Airlines( 79%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 156. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 345 on average our data indicates C$ 632 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$ 355). 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 29 avril 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 202AverageC$ 510FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 380AverageC$ 661FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 547AverageC$ 712FlexibilityNo 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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