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

Our cheapest airline available from Winnipeg to Chicago is WestJet. Our recent data shows that you can find tickets from as low as $184 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $349 and $404 round-trip. Users have found that WestJet is 60% cheaper than the other options available to this destination.

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

The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from Air Canada and Delta, as they are both options that can get you from Winnipeg to Chicago for a low price.

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

Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Winnipeg to Chicago?

While on average a flight from Winnipeg to Chicago is generally $497, our data shows the cheapest flight currently is $176. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $243 for that flight.

What are the most reliable airlines from Winnipeg to Chicago?

No one likes to see their flight delayed. When booking a flight from Winnipeg to Chicago consider choosing SkyWest Airlines (79%), Air Canada (79%) or United Airlines (79%) as they are the most reliable in getting you off to your destination on time.

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

Flights from Winnipeg to Chicago are found to be more expensive on Saturday. 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 Chicago.

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

Find a great deal and save up to 35% by booking at least 49 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 $326.

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

Due to multiple factors, expect to potentially pay more when booking in August. For low rates, June can be a great choice for travel to Chicago. Flights to Chicago from Winnipeg in June are about $463 on average during June, but can be found for as low as $218.

Most accurate provider : When it comes to deals on Winnipeg-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Winnipeg-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly from for flights from Winnipeg to Chicago?

Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago. On average, Winnipeg has 3 outbound flights to Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

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.

$98+ Flights from Winnipeg to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Winnipeg to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in June or February, booked 69 days in advance, depart on a Wednesday or Friday and return on a Saturday

Cheap flight deals from Winnipeg to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$184 (eDestinos)
One-way from	$98 (Kiwi.com)
Popular in	August
Cheapest in	June
Average price	$477
Good round-trip deal	$509 or less
Good one-way deal	$266 or less

Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.

Search Deals

From Winnipeg to Chicago (CHI)

Search Deals

One-way flight from Winnipeg to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 7% potential increase in price ($35 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

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

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 April 17, 2025.

Wed 8/68:30 amYWG - ORD

1 stop8h 14mWestJet

Mon 8/185:30 pmORD - YWG

1 stop26h 46mWestJet

Deal found 4/17

$184

Mon 6/309:00 amYWG - ORD

1 stop7h 55mMultiple Airlines

Wed 7/21:40 pmORD - YWG

1 stop8h 16mMultiple Airlines

Deal found 4/16

$243

Sat 5/176:40 amYWG - ORD

2 stops16h 37mDelta

Mon 5/197:25 pmORD - YWG

2 stops16h 32mDelta

Deal found 4/15

$349

Sat 7/1212:40 pmYWG - MDW

1 stop5h 23mDelta

Wed 7/161:00 pmMDW - YWG

2 stops10h 22mDelta

Deal found 4/17

$370

Thu 5/152:20 pmYWG - ORD

Nonstop2h 28mAir Canada

Thu 5/221:02 pmORD - YWG

Nonstop2h 29mAir Canada

Deal found 4/16

$404

Sat 5/1711:25 amYWG - MDW

2 stops28h 59mPorter Airlines

Wed 5/215:20 pmMDW - YWG

2 stops17h 06mPorter Airlines

Deal found 4/17

$414

Tue 6/177:00 amYWG - ORD

Nonstop2h 31mUnited Airlines

Mon 6/237:58 pmORD - YWG

Nonstop2h 35mUnited Airlines

Deal found 4/17

$417

Mon 6/1612:26 pmYWG - MDW

1 stop5h 14mWestJet

Sat 6/217:21 pmMDW - YWG

1 stop4h 08mWestJet

Deal found 4/16

$472

Fri 10/109:05 pmYWG - MDW

2 stops20h 53mMultiple Airlines

Mon 10/139:15 amMDW - YWG

2 stops11h 31mMultiple Airlines

Deal found 4/16

$518

Best flights from Winnipeg to Chicago
Discover carefully curated flight deals from Winnipeg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2025.

Wed 8/68:30 amYWG - ORD

1 stop8h 14mWestJet

Mon 8/185:30 pmORD - YWG

1 stop26h 46mWestJet

Deal found 4/17

$184

Mon 6/309:00 amYWG - ORD

1 stop7h 55mMultiple Airlines

Wed 7/21:40 pmORD - YWG

1 stop8h 16mMultiple Airlines

Deal found 4/16

$243

Sat 5/176:40 amYWG - ORD

2 stops16h 37mDelta

Mon 5/197:25 pmORD - YWG

2 stops16h 32mDelta

Deal found 4/15

$349

Thu 5/152:20 pmYWG - ORD

Nonstop2h 28mAir Canada

Thu 5/221:02 pmORD - YWG

Nonstop2h 29mAir Canada

Deal found 4/16

$404

Sat 5/1711:25 amYWG - MDW

2 stops28h 59mPorter Airlines

Wed 5/215:20 pmMDW - YWG

2 stops17h 06mPorter Airlines

Deal found 4/17

$414

Tue 6/177:00 amYWG - ORD

Nonstop2h 31mUnited Airlines

Mon 6/237:58 pmORD - YWG

Nonstop2h 35mUnited Airlines

Deal found 4/17

$417

Sat 7/1212:40 pmYWG - MDW

1 stop5h 23mDelta

Wed 7/161:00 pmMDW - YWG

2 stops10h 22mDelta

Deal found 4/17

$370

Mon 6/1612:26 pmYWG - MDW

1 stop5h 14mWestJet

Sat 6/217:21 pmMDW - YWG

1 stop4h 08mWestJet

Deal found 4/16

$472

Fri 10/109:05 pmYWG - MDW

2 stops20h 53mMultiple Airlines

Mon 10/139:15 amMDW - YWG

2 stops11h 31mMultiple Airlines

Deal found 4/16

$518

Last-minute flights from Winnipeg to Chicago
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated April 17, 2025 and is based on user searches.

Fri 4/255:00 pmYWG - ORD

1 stop19h 29mMultiple Airlines

Mon 4/285:34 pmORD - YWG

2 stops24h 07mMultiple Airlines

Deal found 4/16

$454

Sat 4/262:20 pmYWG - ORD

Nonstop2h 28mAir Canada

Wed 5/712:57 pmORD - YWG

Nonstop2h 34mAir Canada

Deal found 4/16

$550

Sat 4/262:20 pmYWG - ORD

Nonstop2h 28mUnited Airlines

Wed 5/79:17 pmORD - YWG

1 stop15h 52mUnited Airlines

Deal found 4/16

$560

Sat 4/2612:32 pmYWG - ORD

2 stops11h 27mDelta

Wed 5/75:30 amORD - YWG

1 stop10h 58mDelta

Deal found 4/16

$565

Tue 4/2910:45 amYWG - MDW

2 stops11h 37mMultiple Airlines

Sat 5/39:40 amMDW - YWG

2 stops24h 46mMultiple Airlines

Deal found 4/17

$566

Thu 5/152:20 pmYWG - ORD

Nonstop2h 28mAir Canada

Thu 5/221:02 pmORD - YWG

Nonstop2h 29mAir Canada

Deal found 4/16

$404

Sat 5/176:40 amYWG - ORD

2 stops16h 37mDelta

Mon 5/197:25 pmORD - YWG

2 stops16h 32mDelta

Deal found 4/15

$349

Sat 5/1711:25 amYWG - MDW

2 stops28h 59mPorter Airlines

Wed 5/215:20 pmMDW - YWG

2 stops17h 06mPorter Airlines

Deal found 4/17

$414

Fri 5/238:25 pmYWG - ORD

2 stops20h 19mMultiple Airlines

Wed 5/288:37 amORD - YWG

1 stop31h 41mMultiple Airlines

Deal found 4/16

$271

Fri 5/238:30 amYWG - MDW

1 stop4h 45mDelta

Wed 5/281:08 pmMDW - YWG

2 stops10h 17mDelta

Deal found 4/16

$392

Tue 5/278:30 amYWG - ORD

1 stop8h 14mWestJet

Wed 5/2811:03 amORD - YWG

1 stop12h 22mWestJet

Deal found 4/16

$351

Tue 5/272:20 pmYWG - ORD

Nonstop2h 31mUnited Airlines

Wed 5/287:58 pmORD - YWG

Nonstop2h 35mUnited Airlines

Deal found 4/17

$417

One-way flights from Winnipeg to Chicago
Search for one-way flight options from Winnipeg to Chicago. Find affordable one-way fares based on user searches. Data last updated April 17, 2025.

Tue 9/28:30 amYWG - ORD

1 stop8h 13mWestJet

Deal found 4/16

$98

Thu 6/59:00 amYWG - ORD

1 stop14h 59mMultiple Airlines

Deal found 4/17

$151

Thu 6/56:30 amYWG - MDW

2 stops16h 48mMultiple Airlines

Deal found 4/17

$187

Sun 6/157:00 amYWG - ORD

Nonstop2h 31mAir Canada

Deal found 4/16

$227

Sat 7/1212:40 pmYWG - MDW

1 stop5h 23mDelta

Deal found 4/16

$239

Sat 7/126:40 amYWG - ORD

2 stops5h 58mDelta

Deal found 4/16

$239

Sat 7/126:40 amYWG - MDW

1 stop11h 23mWestJet

Deal found 4/16

$250

Thu 5/12:20 pmYWG - ORD

Nonstop2h 28mUnited Airlines

Deal found 4/16

$286

Cheapflights Fare Finder

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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 8/6

8:30 am-4:44 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 8/18

5:30 pm-8:16 pm

1 stop26h 46m

$184

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 6/30

9:00 am-4:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Wed 7/2

1:40 pm-9:56 pm

1 stop8h 16m

$243

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/17

6:40 am-11:17 pm

2 stops16h 37m

Chicago O'Hare Intl

Mon 5/19

7:25 pm-11:57 am

2 stops16h 32m

$349

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/12

12:40 pm-6:03 pm

1 stop5h 23m

Chicago Midway

Wed 7/16

1:00 pm-11:22 pm

2 stops10h 22m

$370

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/15

2:20 pm-4:48 pm

Nonstop2h 28m

Chicago O'Hare Intl

Thu 5/22

1:02 pm-3:31 pm

Nonstop2h 29m

$404

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 5/17

11:25 am-4:24 pm

2 stops28h 59m

Chicago Midway

Wed 5/21

5:20 pm-10:26 am

2 stops17h 06m

$414

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 6/17

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Mon 6/23

7:58 pm-10:33 pm

Nonstop2h 35m

$417

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 6/16

12:26 pm-5:40 pm

1 stop5h 14m

Chicago Midway

Sat 6/21

7:21 pm-11:29 pm

1 stop4h 08m

$472

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/10

9:05 pm-5:58 pm

2 stops20h 53m

Chicago Midway

Mon 10/13

9:15 am-8:46 pm

2 stops11h 31m

$518

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/2

8:30 am-4:43 pm

1 stop8h 13m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 17 results

Compare providers for flights from Winnipeg to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Chicago in April.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Winnipeg-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Winnipeg-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

The price you pay for your flight from Winnipeg to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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?

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the morning.

Weekly flight availability from Winnipeg to Chicago

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Winnipeg to Chicago, such as Porter Airlines, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

281 reviews

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

281 reviews

Porter Airlines

8.0

Very good

281 reviews

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

7,917 reviews

Porter Airlines

8.0

Very good

281 reviews

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

8,667 reviews

Porter Airlines

8.0

Very good

281 reviews

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

2,809 reviews

Porter Airlines

8.0

Very good

281 reviews

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

9,142 reviews

Porter Airlines

8.0

Very good

281 reviews

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

What airport do you fly from for flights from Winnipeg to Chicago?
Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago. On average, Winnipeg has 3 outbound flights to Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.
What are the cheapest airlines flying from Winnipeg to Chicago round-trip?
Our cheapest airline available from Winnipeg to Chicago is WestJet. Our recent data shows that you can find tickets from as low as $184 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $349 and $404 round-trip. Users have found that WestJet is 60% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Winnipeg to Chicago one-way?
The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from Air Canada and Delta, 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?
No one likes to see their flight delayed. When booking a flight from Winnipeg to Chicago consider choosing SkyWest Airlines (79%), Air Canada (79%) or United Airlines (79%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Winnipeg to Chicago?
While on average a flight from Winnipeg to Chicago is generally $497, our data shows the cheapest flight currently is $176. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $243 for that flight.
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, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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

Merrillville

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

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Top 2 airlines flying from Winnipeg to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	Cheapest$239	Average$572	FlexibilityNo cancel fee	On-time67%
United Airlines	Cheapest$443	Average$547	FlexibilityNo cancel fee	On-time69%

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$98+ Cheap flights from Winnipeg (YWG) to Chicago (CHI)

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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Winnipeg to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in June or February, booked 69 days in advance, depart on a Wednesday or Friday and return on a Saturday

Cheap flight deals from Winnipeg to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Winnipeg to Chicago

Cheapest flights from Winnipeg to ChicagoExplore 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 April 17, 2025.

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 April 17, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Compare providers for flights from Winnipeg to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Chicago in April.

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.

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 April 11, 2025.

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

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 April 17, 2025.

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 April 17, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Winnipeg to Chicago, such as Porter Airlines, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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?

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

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

What are the most reliable airlines from Winnipeg to Chicago?

What are the cheapest flights from Winnipeg to Chicago?

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

How can I find direct flights from Winnipeg to Chicago?

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

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

Traveling to a place near Winnipeg?

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.

Top 2 airlines flying from Winnipeg to Chicago

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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 April 17, 2025.