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 $328 on this airline. Additional options worth looking into are Air Canada and Delta, starting at $377 and $428 round-trip. Users have found that WestJet is 29% 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 $161. However, be on the lookout for offers from Air Canada and United Airlines, 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 $567, our data shows the cheapest flight currently is $152. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $282 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 (71%), Air Canada (71%) or United Airlines (71%) 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 9% by booking at least 15 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 $467 on average during June, but can be found for as low as $266.

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 FlightHub the most. FlightHub 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.

$114+ Flights from Winnipeg to Chicago

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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.

The best prices from Winnipeg to Chicago are usually found in June or March, booked 70 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Winnipeg to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$328 (Mytrip)
One-way from	$114 (Trip.com)
Popular in	August
Cheapest in	June
Average price	$524
Good round-trip deal	$413 or less
Good one-way deal	$259 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. 6% potential increase in price ($30 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in January 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 January 30, 2025.

Sat 9/208:30 amYWG - ORD

1 stop8h 13mWestJet

Sun 9/215:30 pmORD - YWG

1 stop18h 11mWestJet

Deal found 1/28

$291

Sat 9/204:15 pmYWG - ORD

1 stop6h 10mUnited Airlines

Sun 9/217:30 amORD - YWG

2 stops15h 50mUnited Airlines

Deal found 1/28

$330

Thu 3/136:20 amYWG - ORD

2 stops22h 25mMultiple Airlines

Mon 3/174:45 pmORD - YWG

2 stops24h 50mMultiple Airlines

Deal found 1/29

$342

Wed 3/57:30 amYWG - ORD

1 stop7h 21mAir Canada

Wed 3/1211:04 amORD - YWG

1 stop8h 09mAir Canada

Deal found 1/29

$377

Wed 3/512:45 pmYWG - ORD

1 stop9h 13mDelta

Wed 3/125:00 pmORD - YWG

2 stops6h 29mDelta

Deal found 1/29

$428

Wed 3/2612:53 pmYWG - MDW

1 stop5h 25mDelta

Tue 4/11:16 pmMDW - YWG

1 stop6h 59mDelta

Deal found 1/29

$447

Fri 2/77:30 amYWG - MDW

2 stops16h 47mMultiple Airlines

Sun 2/92:01 pmMDW - YWG

1 stop10h 40mMultiple Airlines

Deal found 1/29

$448

Tue 8/266:30 amYWG - MDW

2 stops10h 31mWestJet

Sun 8/319:20 amMDW - YWG

1 stop14h 02mWestJet

Deal found 1/29

$483

Thu 3/2711:35 amYWG - MDW

2 stops22h 45mPorter Airlines

Tue 4/15:35 pmMDW - YWG

2 stops24h 24mPorter Airlines

Deal found 1/29

$593

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 January 30, 2025.

Thu 3/136:20 amYWG - ORD

1 stop9h 36mWestJet

Mon 3/174:45 pmORD - YWG

2 stops18h 30mWestJet

Deal found 1/29

$328

Thu 3/136:20 amYWG - ORD

2 stops22h 25mMultiple Airlines

Mon 3/174:45 pmORD - YWG

2 stops24h 50mMultiple Airlines

Deal found 1/29

$342

Wed 3/57:30 amYWG - ORD

1 stop7h 21mAir Canada

Wed 3/1211:04 amORD - YWG

1 stop8h 09mAir Canada

Deal found 1/29

$377

Wed 3/512:45 pmYWG - ORD

1 stop9h 13mDelta

Wed 3/125:00 pmORD - YWG

2 stops6h 29mDelta

Deal found 1/29

$428

Mon 4/712:05 pmYWG - ORD

1 stop7h 25mUnited Airlines

Fri 4/2512:57 pmORD - YWG

Nonstop2h 34mUnited Airlines

Deal found 1/29

$448

Thu 3/2711:35 amYWG - MDW

2 stops22h 45mPorter Airlines

Tue 4/15:35 pmMDW - YWG

2 stops24h 24mPorter Airlines

Deal found 1/29

$593

Wed 3/2612:53 pmYWG - MDW

1 stop5h 25mDelta

Tue 4/11:16 pmMDW - YWG

1 stop6h 59mDelta

Deal found 1/29

$447

Thu 3/135:15 pmYWG - MDW

2 stops17h 05mMultiple Airlines

Mon 3/1711:15 amMDW - YWG

2 stops12h 17mMultiple Airlines

Deal found 1/29

$458

Wed 3/56:20 amYWG - MDW

2 stops27h 52mWestJet

Wed 3/121:16 pmMDW - YWG

1 stop6h 59mWestJet

Deal found 1/29

$498

Last-minute flights from Winnipeg to Chicago
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated January 30, 2025 and is based on user searches.

Mon 2/37:30 amYWG - MDW

1 stop8h 50mDelta

Thu 2/610:19 amMDW - YWG

1 stop6h 24mDelta

Deal found 1/29

$1,082

Thu 2/66:20 amYWG - ORD

2 stops16h 53mMultiple Airlines

Sun 2/910:47 pmORD - YWG

1 stop25h 45mMultiple Airlines

Deal found 1/28

$353

Thu 2/67:15 amYWG - ORD

1 stop7h 30mAir Canada

Sat 2/82:05 pmORD - YWG

1 stop6h 53mAir Canada

Deal found 1/28

$584

Thu 2/65:37 pmYWG - MDW

1 stop24h 06mWestJet

Sun 2/911:19 amMDW - YWG

1 stop24h 32mWestJet

Deal found 1/28

$648

Fri 2/77:30 amYWG - MDW

2 stops16h 47mMultiple Airlines

Sun 2/92:01 pmMDW - YWG

1 stop10h 40mMultiple Airlines

Deal found 1/29

$448

Fri 2/78:15 amYWG - ORD

2 stops13h 07mWestJet

Tue 2/1110:10 amORD - YWG

1 stop6h 33mWestJet

Deal found 1/28

$664

Fri 2/74:30 pmYWG - ORD

1 stop7h 29mUnited Airlines

Sun 2/912:56 pmORD - YWG

Nonstop2h 32mUnited Airlines

Deal found 1/29

$681

Wed 2/125:00 amYWG - ORD

2 stops7h 55mWestJet

Tue 2/257:10 pmORD - YWG

1 stop4h 28mWestJet

Deal found 1/29

$542

Wed 2/125:00 amYWG - MDW

2 stops8h 05mWestJet

Tue 2/251:26 pmMDW - YWG

1 stop10h 12mWestJet

Deal found 1/29

$575

Wed 2/1912:15 pmYWG - ORD

1 stop7h 22mAir Canada

Wed 2/262:05 pmORD - YWG

1 stop6h 53mAir Canada

Deal found 1/29

$380

Wed 2/196:40 amYWG - ORD

1 stop8h 50mDelta

Wed 2/264:58 pmORD - YWG

2 stops6h 40mDelta

Deal found 1/29

$464

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 January 30, 2025.

Tue 2/257:30 amYWG - ORD

1 stop9h 01mMultiple Airlines

Deal found 1/29

$114

Tue 5/139:05 pmYWG - MDW

2 stops14h 21mMultiple Airlines

Deal found 1/29

$119

Mon 4/218:15 amYWG - ORD

1 stop7h 41mWestJet

Deal found 1/29

$161

Wed 3/52:15 pmYWG - ORD

Nonstop2h 22mAir Canada

Deal found 1/29

$220

Wed 3/262:15 pmYWG - ORD

Nonstop2h 22mUnited Airlines

Deal found 1/29

$245

Sat 3/295:43 pmYWG - ORD

1 stop4h 02mDelta

Deal found 1/29

$250

Wed 3/266:00 amYWG - MDW

2 stops12h 18mWestJet

Deal found 1/29

$276

Tue 2/2511:35 amYWG - MDW

2 stops24h 35mPorter Airlines

Deal found 1/29

$291

Tue 2/117:30 amYWG - MDW

2 stops10h 41mDelta

Deal found 1/29

$336

Find flights from Winnipeg to Chicago within your budget

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

6:20 am-3:56 pm

1 stop9h 36m

Chicago O'Hare Intl

Mon 3/17

4:45 pm-11:15 am

2 stops18h 30m

$328

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

6:20 am-4:45 am

2 stops22h 25m

Chicago O'Hare Intl

Mon 3/17

4:45 pm-5:35 pm

2 stops24h 50m

$342

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 3/5

7:30 am-2:51 pm

1 stop7h 21m

Chicago O'Hare Intl

Wed 3/12

11:04 am-7:13 pm

1 stop8h 09m

$377

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 3/5

12:45 pm-9:58 pm

1 stop9h 13m

Chicago O'Hare Intl

Wed 3/12

5:00 pm-11:29 pm

2 stops6h 29m

$428

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 3/26

12:53 pm-6:18 pm

1 stop5h 25m

Chicago Midway

Tue 4/1

1:16 pm-8:15 pm

1 stop6h 59m

$447

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 4/7

12:05 pm-7:30 pm

1 stop7h 25m

Chicago O'Hare Intl

Fri 4/25

12:57 pm-3:31 pm

Nonstop2h 34m

$448

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 3/13

5:15 pm-10:20 am

2 stops17h 05m

Chicago Midway

Mon 3/17

11:15 am-11:32 pm

2 stops12h 17m

$458

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 3/5

6:20 am-10:12 am

2 stops27h 52m

Chicago Midway

Wed 3/12

1:16 pm-8:15 pm

1 stop6h 59m

$498

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 3/27

11:35 am-10:20 am

2 stops22h 45m

Chicago Midway

Tue 4/1

5:35 pm-5:59 pm

2 stops24h 24m

$593

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 2/25

7:30 am-4:31 pm

1 stop9h 01m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 18 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 January.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
oojo	Price Accuracy3 stars	Trust Score*2 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 FlightHub the most. FlightHub 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.

Travel insights for flights from Winnipeg to Chicago

Get recent, data-driven insights about flights from Winnipeg to Chicago including ideal travel times, pricing trends, and more.

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 70 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 $325). 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 at noon. If you’re flexible enough to do this you can expect to save up to 27% 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 Delta, Porter Airlines and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

8,450 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

8,450 reviews

Delta

8.0

Very good

8,450 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines

7.9

Good

278 reviews

Delta

8.0

Very good

8,450 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines

7.4

Good

8,906 reviews

Delta

8.0

Very good

8,450 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet

7.2

Good

2,817 reviews

Delta

8.0

Very good

8,450 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada

7.0

Good

8,641 reviews

Delta

8.0

Very good

8,450 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $328 on this airline. Additional options worth looking into are Air Canada and Delta, starting at $377 and $428 round-trip. Users have found that WestJet is 29% 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 $161. However, be on the lookout for offers from Air Canada and United Airlines, 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 (71%), Air Canada (71%) or United Airlines (71%) 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 $567, our data shows the cheapest flight currently is $152. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $282 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 $325). 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

New Buffalo

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$291	Average$556	FlexibilityNo cancel fee	On-time67%
United Airlines	Cheapest$443	Average$547	FlexibilityNo cancel fee	On-time69%

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$114+ 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 2/25. 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

The best prices from Winnipeg to Chicago are usually found in June or March, booked 70 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 January 30, 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 January 30, 2025.

Find flights from Winnipeg to Chicago within your budget

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 January.

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.

Travel insights for flights from Winnipeg to Chicago

Get recent, data-driven insights about flights from Winnipeg to Chicago including ideal travel times, pricing trends, and more.

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 January 24, 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 January 30, 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 January 30, 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 Delta, Porter Airlines 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 January 30, 2025.