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Cheap flights from Winnipeg to Chicago from C$ 257

This is the cheapest one-way flight price, found on 27/11. Prices may vary by date and flight preferences.
YWG — CHI
4 Dec — 11 Dec1
1 adult
Mon 4/12
Mon 11/12

The best prices from Winnipeg to Chicago are usually found in April or January, booked 23 days in advance, depart on a Saturday or Tuesday and return on a Monday

How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)

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 November 2023.

Popular in

March

Cheapest in

April

Round-trip from

C$ 501

One-way from

C$ 333
High demand for flights, 14% potential price rise
Best time to find cheap flights, 17% potential price drop
From Winnipeg to Chicago (CHI)
One-way flight from Winnipeg to Chicago (CHI)

YWG - CHI

Price

C$ 369 - C$ 620

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

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

Friday is generally a great day to depart. Flying on this day could help you save up to 19%.

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

Find a great deal and save up to 237% by booking at least 24 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago within the next two weeks, with the cheapest ticket starting at C$ 807.

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

The best pricing can be found in the month of April. Prices to Chicago from Winnipeg average C$ 723. You can even find prices in April for less than C$ 723, as users have found deals to Chicago from as low as C$ 467. The month of March appears to be one of the more expensive times to travel to Chicago from Winnipeg. Flying in the targeted month can save you up to 16%.

When is the cheapest time to fly from Winnipeg to Chicago (YWG - CHI)?

One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 36% on airfare.

Cheap Delta flights from Winnipeg to Chicago

Explore cheap flight options specifically provided by Delta for the route between Winnipeg and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 508,424 searches. Data last updated 29 November 2023.
Check out some of the cheapest Delta flights we've come across from Winnipeg to Chicago. It's recommended that users confirm their flight details before booking.

Cheap WestJet flights from Winnipeg to Chicago

Explore cheap flight options specifically provided by WestJet for the route between Winnipeg and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 508,424 searches. Data last updated 29 November 2023.
Browse through some of the cheapest WestJet flights travelling from Winnipeg to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.

Cheap Winnipeg to Chicago flights in November & December 2023

Find cheap flight options from Winnipeg to Chicago specifically for the months of November and December 2023. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 508,424 searches. Prices were last updated on 29 November 2023.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2023. If these deals don't appeal to you, be sure to come back soon for more options.

Winnipeg to Chicago 2023 flight deals

Discover exclusive flight deals for travel between Winnipeg and Chicago in 2023. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 508,424 searches. Data last updated 29 November 2023.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2023. If these deals don't appeal to you, be sure to come back soon for more options.

One-way flights to Chicago from Winnipeg

Search for one-way flight options from Winnipeg to Chicago. 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 508,424 searches. Data last updated 29 November 2023.
Users in need of a one-way flight from Winnipeg to Chicago can choose from these deals. For those needing a return trip from Winnipeg, there is a search form available above.

Find flights from Winnipeg to Chicago within your budget

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 508,424 searches. Data last updated 29 November 2023.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 591 - C$ 832

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 22/2

2 stops19h 40m

Chicago O'Hare Intl

Mon 26/2

2 stops20h 55m

C$ 591

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 10/2

1 stop6h 27m

Chicago O'Hare Intl

Tue 13/2

1 stop6h 42m

C$ 601

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 10/2

2 stops8h 58m

Chicago O'Hare Intl

Tue 13/2

1 stop5h 10m

C$ 607

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 4/4

1 stop8h 37m

Chicago O'Hare Intl

Sat 6/4

1 stop6h 47m

C$ 610

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 3/4

1 stop6h 38m

Chicago O'Hare Intl

Sun 7/4

1 stop14h 56m

C$ 652

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 3/4

1 stop13h 27m

Chicago O'Hare Intl

Sun 7/4

2 stops17h 07m

C$ 674

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Thu 22/2

1 stop8h 32m

Chicago Midway

Mon 26/2

1 stop16h 50m

C$ 679

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 22/2

2 stops15h 16m

Chicago O'Hare Intl

Mon 26/2

1 stop19h 30m

C$ 679

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 30/12

1 stop5h 11m

Chicago O'Hare Intl

Tue 2/1

1 stop5h 46m

C$ 832

Flights are sorted by cheapest first

Deals found on 29/11

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 November 2023.
Get a feel of what it's like to fly with Delta, WestJet and Air Canada 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.
WestJet Encore
10.0
Wonderful
2 reviews

Overall

10.0

Boarding

10.0

Entertainment

10.0

Food

10.0

Crew

10.0

Comfort

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

WestJet Encore
10.0
Wonderful
2 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Overall

10.0

Boarding

10.0

Entertainment

10.0

Food

10.0

Crew

10.0

Comfort

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.9
Good
3,035 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Overall

10.0

Boarding

10.0

Entertainment

10.0

Food

10.0

Crew

10.0

Comfort

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.2
Good
918 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Overall

10.0

Boarding

10.0

Entertainment

10.0

Food

10.0

Crew

10.0

Comfort

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.0
Good
670 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Overall

10.0

Boarding

10.0

Entertainment

10.0

Food

10.0

Crew

10.0

Comfort

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

6.7
Okay
988 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Overall

10.0

Boarding

10.0

Entertainment

10.0

Food

10.0

Crew

10.0

Comfort

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

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 0 flights from Winnipeg to Chicago per day from 6 different airlines.

Can I find flights from Winnipeg to Chicago for under C$ 600 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago for under C$ 600. The cheapest flight booked recently is on Delta for just C$ 591, but on average you can expect to pay C$ 719.

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

Delta, at C$ 591, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Air Canada and WestJet. Delta is priced at 18% 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 Air Canada, with whom users have recently found tickets for as low as C$ 257. However, be on the lookout for offers from WestJet and WestJet Encore, as they are both options that can get you from Winnipeg to Chicago for a low price.

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

What does YWG to ORD mean?

Great question - YWG to ORD just means Winnipeg Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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.

Top 6 airlines flying from Winnipeg to Chicago

Discover the top 6 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 508,424 searches. Data last updated 29 November 2023.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapestC$ 418AverageC$ 630FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 432AverageC$ 594FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Endeavor AirlinesCheapestC$ 459AverageC$ 861FlexibilityNo cancel feeOn-timeN/A
Search Endeavor Airlines flights
United AirlinesCheapestC$ 475AverageC$ 732FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 512AverageC$ 721FlexibilityNo cancel feeOn-time60%
Search WestJet flights
WestJet EncoreCheapestC$ 785AverageC$ 796FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore flights

Search flights to Chicago by cabin class

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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