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

WestJet, at C$ 372, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Porter Airlines and Delta. WestJet is priced at 44% 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 WestJet, with whom users have recently found tickets for as low as C$ 279. However, be on the lookout for offers from Porter Airlines and Air Canada, as they are both options that can get you from Winnipeg to Chicago for a low price.

What are the cheapest flights from Winnipeg to Chicago?

Looking at all options, your cheapest flight can be booked for C$ 197. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 303 on average our data indicates C$ 1,805 when flying from Winnipeg to Chicago.

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 (66%), Air Canada (66%), United Airlines( 66%).

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

Air Canada, Delta and United Airlines are the most popular airlines when flying from Winnipeg to Chicago.

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

Tuesday is generally a great day to depart. Flying on this day could help you save up to 14%.

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

Find a great deal and save up to 6% 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 C$ 469.

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

The best pricing can be found in the month of June. Prices to Chicago from Winnipeg average C$ 669. You can even find prices in June for less than C$ 669, as users have found deals to Chicago from as low as C$ 403. The month of August 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 12%.

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 4 different airlines.

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.

C$ 210+ Flights from Winnipeg to Chicago

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

Cheap flight deals from Winnipeg to Chicago

Round-trip from	C$ 372
One-way from	C$ 210
Popular in	August
Cheapest in	June
Average price	C$ 623
Good round-trip deal	C$ 573 or less
Good one-way deal	C$ 238 or less

WestJet
27/5-28/5
2 total stops
23h 45m total
Winnipeg to Chicago

Search Deals

3/5
1 total stop
22h 24m total
Winnipeg to Chicago

Search Deals

Highest demand for flights based on searches. 6% potential increase in price (C$ 64 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (C$ 12 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in February 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 27 February 2025.

Tue 27/58:30 a.m.YWG - ORD

1 stop8h 14mWestJet

Wed 28/55:30 p.m.ORD - YWG

1 stop15h 31mWestJet

Deal found 26/2C$ 372

Sat 3/56:30 a.m.YWG - ORD

3 stops26h 05mMultiple Airlines

Sun 4/51:47 p.m.ORD - YWG

2 stops26h 41mMultiple Airlines

Deal found 27/2C$ 408

Thu 27/311:35 a.m.YWG - MDW

2 stops29h 05mPorter Airlines

Mon 31/35:35 p.m.MDW - YWG

3 stops24h 24mPorter Airlines

Deal found 27/2C$ 518

Tue 8/48:50 a.m.YWG - ORD

1 stop8h 37mDelta

Tue 15/412:15 p.m.ORD - YWG

1 stop8h 04mDelta

Deal found 27/2C$ 549

Thu 27/37:30 a.m.YWG - ORD

1 stop7h 21mAir Canada

Mon 31/312:57 p.m.ORD - YWG

Nonstop2h 34mAir Canada

Deal found 27/2C$ 611

Sat 26/42:20 p.m.YWG - ORD

Nonstop2h 28mUnited Airlines

Wed 7/512:57 p.m.ORD - YWG

Nonstop2h 34mUnited Airlines

Deal found 27/2C$ 623

Sun 13/46:50 a.m.YWG - MDW

1 stop7h 27mDelta

Sun 20/43:02 p.m.MDW - YWG

2 stops8h 26mDelta

Deal found 26/2C$ 628

Sat 3/511:45 a.m.YWG - MDW

2 stops20h 34mMultiple Airlines

Sun 4/55:20 p.m.MDW - YWG

1 stop15h 35mMultiple Airlines

Deal found 27/2C$ 712

Tue 8/46:50 a.m.YWG - MDW

1 stop7h 27mWestJet

Tue 15/47:00 p.m.MDW - YWG

1 stop21h 53mWestJet

Deal found 27/2C$ 719

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 27 February 2025.

Tue 27/58:30 a.m.YWG - ORD

1 stop8h 14mWestJet

Wed 28/55:30 p.m.ORD - YWG

1 stop15h 31mWestJet

Deal found 26/2C$ 372

Sat 3/56:30 a.m.YWG - ORD

3 stops26h 05mMultiple Airlines

Sun 4/51:47 p.m.ORD - YWG

2 stops26h 41mMultiple Airlines

Deal found 27/2C$ 408

Thu 27/311:35 a.m.YWG - MDW

2 stops29h 05mPorter Airlines

Mon 31/35:35 p.m.MDW - YWG

3 stops24h 24mPorter Airlines

Deal found 27/2C$ 518

Tue 8/48:50 a.m.YWG - ORD

1 stop8h 37mDelta

Tue 15/412:15 p.m.ORD - YWG

1 stop8h 04mDelta

Deal found 27/2C$ 549

Thu 27/37:30 a.m.YWG - ORD

1 stop7h 21mAir Canada

Mon 31/312:57 p.m.ORD - YWG

Nonstop2h 34mAir Canada

Deal found 27/2C$ 611

Sat 26/42:20 p.m.YWG - ORD

Nonstop2h 28mUnited Airlines

Wed 7/512:57 p.m.ORD - YWG

Nonstop2h 34mUnited Airlines

Deal found 27/2C$ 623

Sun 13/46:50 a.m.YWG - MDW

1 stop7h 27mDelta

Sun 20/43:02 p.m.MDW - YWG

2 stops8h 26mDelta

Deal found 26/2C$ 628

Sat 3/511:45 a.m.YWG - MDW

2 stops20h 34mMultiple Airlines

Sun 4/55:20 p.m.MDW - YWG

1 stop15h 35mMultiple Airlines

Deal found 27/2C$ 712

Tue 8/46:00 a.m.YWG - MDW

2 stops12h 18mWestJet

Tue 15/412:48 p.m.MDW - YWG

2 stops11h 56mWestJet

Deal found 27/2C$ 719

Direct flights from Winnipeg to Chicago
Explore direct flight options from Winnipeg to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 27 February 2025.

Sat 26/42:20 p.m.YWG - ORD

Nonstop2h 28mUnited Airlines

Wed 7/512:57 p.m.ORD - YWG

Nonstop2h 34mUnited Airlines

Deal found 27/2C$ 623

Sat 26/42:20 p.m.YWG - ORD

Nonstop2h 28mAir Canada

Tue 6/512:57 p.m.ORD - YWG

Nonstop2h 34mAir Canada

Deal found 26/2C$ 624

Last-minute flights from Winnipeg to Chicago
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated 27 February 2025 and is based on user searches.

Thu 6/34:30 p.m.YWG - ORD

1 stop6h 15mUnited Airlines

Fri 14/35:00 a.m.ORD - YWG

1 stop8h 27mUnited Airlines

Deal found 27/2C$ 887

Thu 6/36:40 a.m.YWG - MDW

2 stops6h 25mDelta

Fri 14/32:55 p.m.MDW - YWG

2 stops8h 34mDelta

Deal found 27/2C$ 925

Thu 6/36:40 a.m.YWG - ORD

2 stops6h 15mDelta

Fri 14/310:25 a.m.ORD - YWG

2 stops9h 50mDelta

Deal found 27/2C$ 925

Fri 7/312:45 p.m.YWG - ORD

1 stop26h 29mWestJet

Sun 9/34:45 p.m.ORD - YWG

2 stops15h 38mWestJet

Deal found 27/2C$ 830

Fri 7/35:37 p.m.YWG - MDW

1 stop24h 06mWestJet

Sun 9/39:25 a.m.MDW - YWG

2 stops15h 09mWestJet

Deal found 27/2C$ 942

Fri 7/37:45 a.m.YWG - ORD

1 stop7h 00mAir Canada

Sun 9/312:58 p.m.ORD - YWG

Nonstop2h 30mAir Canada

Deal found 27/2C$ 975

Fri 21/36:50 a.m.YWG - MDW

2 stops5h 46mDelta

Mon 24/39:25 a.m.MDW - YWG

2 stops10h 50mDelta

Deal found 27/2C$ 709

Wed 26/36:50 a.m.YWG - ORD

1 stop8h 25mDelta

Sun 30/39:40 a.m.ORD - YWG

1 stop7h 13mDelta

Deal found 27/2C$ 627

Wed 26/36:00 a.m.YWG - ORD

2 stops11h 28mWestJet

Sun 30/39:40 a.m.ORD - YWG

1 stop10h 35mWestJet

Deal found 27/2C$ 751

Wed 26/36:00 a.m.YWG - MDW

2 stops12h 18mWestJet

Sun 30/37:09 p.m.MDW - YWG

1 stop25h 06mWestJet

Deal found 27/2C$ 790

Thu 27/311:35 a.m.YWG - MDW

2 stops29h 05mPorter Airlines

Mon 31/35:35 p.m.MDW - YWG

3 stops24h 24mPorter Airlines

Deal found 27/2C$ 518

Thu 27/39:00 a.m.YWG - ORD

2 stops10h 15mMultiple Airlines

Mon 31/39:01 p.m.ORD - YWG

2 stops18h 07mMultiple Airlines

Deal found 27/2C$ 588

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 27 February 2025.

Sat 3/56:20 p.m.YWG - ORD

1 stop22h 24mMultiple Airlines

Deal found 27/2C$ 210

Sun 23/37:30 a.m.YWG - MDW

1 stop28h 04mMultiple Airlines

Deal found 26/2C$ 237

Sat 12/74:30 p.m.YWG - ORD

1 stop20h 09mWestJet

Deal found 27/2C$ 279

Sat 3/55:00 a.m.YWG - MDW

1 stop27h 19mPorter Airlines

Deal found 27/2C$ 309

Sat 3/52:20 p.m.YWG - ORD

Nonstop2h 28mAir Canada

Deal found 27/2C$ 347

Sat 3/58:00 a.m.YWG - MDW

2 stops10h 20mDelta

Deal found 27/2C$ 361

Sat 12/710:45 a.m.YWG - MDW

2 stops7h 43mWestJet

Deal found 27/2C$ 463

Mon 10/34:30 p.m.YWG - ORD

1 stop7h 53mUnited Airlines

Deal found 26/2C$ 687

Mon 10/35:00 a.m.YWG - ORD

2 stops11h 15mDelta

Deal found 26/2C$ 733

Find flights from Winnipeg to Chicago within your budget

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 27/5

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

1 stop8h 14m

Chicago O'Hare Intl

Wed 28/5

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 372

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 3/5

6:30 a.m.-8:35 a.m.

3 stops26h 05m

Chicago O'Hare Intl

Sun 4/5

1:47 p.m.-4:28 p.m.

2 stops26h 41m

C$ 408

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 27/3

11:35 a.m.-4:40 p.m.

2 stops29h 05m

Chicago Midway

Mon 31/3

5:35 p.m.-5:59 p.m.

3 stops24h 24m

C$ 518

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 8/4

8:50 a.m.-5:27 p.m.

1 stop8h 37m

Chicago O'Hare Intl

Tue 15/4

12:15 p.m.-8:19 p.m.

1 stop8h 04m

C$ 549

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 27/3

7:30 a.m.-2:51 p.m.

1 stop7h 21m

Chicago O'Hare Intl

Mon 31/3

12:57 p.m.-3:31 p.m.

Nonstop2h 34m

C$ 611

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 26/4

2:20 p.m.-4:48 p.m.

Nonstop2h 28m

Chicago O'Hare Intl

Wed 7/5

12:57 p.m.-3:31 p.m.

Nonstop2h 34m

C$ 623

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 13/4

6:50 a.m.-2:17 p.m.

1 stop7h 27m

Chicago Midway

Sun 20/4

3:02 p.m.-11:28 p.m.

2 stops8h 26m

C$ 628

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 3/5

11:45 a.m.-8:19 a.m.

2 stops20h 34m

Chicago Midway

Sun 4/5

5:20 p.m.-8:55 a.m.

1 stop15h 35m

C$ 712

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 8/4

6:00 a.m.-6:18 p.m.

2 stops12h 18m

Chicago Midway

Tue 15/4

12:48 p.m.-12:44 a.m.

2 stops11h 56m

C$ 719

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 3/5

6:20 p.m.-4:44 p.m.

1 stop22h 24m

C$ 210

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/2

Showing 1-10 of 18 results

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 best time to book flights from Winnipeg to Chicago is 70 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?

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 28% on airfare.

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 Sunday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 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

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 a feel of what it's like to fly with Delta, Porter Airlines 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.

Delta

8.0

Very good

8,138 reviews

Check prices

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

8,138 reviews

Delta

8.0

Very good

8,138 reviews

Check prices

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

8,138 reviews

Check prices

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

8,724 reviews

Delta

8.0

Very good

8,138 reviews

Check prices

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

2,794 reviews

Delta

8.0

Very good

8,138 reviews

Check prices

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

8,801 reviews

Delta

8.0

Very good

8,138 reviews

Check prices

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?
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 4 different airlines.
What are the cheapest airlines flying from Winnipeg to Chicago round-trip?
WestJet, at C$ 372, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Porter Airlines and Delta. WestJet is priced at 44% 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 WestJet, with whom users have recently found tickets for as low as C$ 279. However, be on the lookout for offers from Porter Airlines 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 (66%), Air Canada (66%), United Airlines( 66%).
What are the cheapest flights from Winnipeg to Chicago?
Looking at all options, your cheapest flight can be booked for C$ 197. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 303 on average our data indicates C$ 1,805 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

Top 4 airlines flying from Winnipeg to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	CheapestC$ 487	AverageC$ 731	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
WestJet	CheapestC$ 495	AverageC$ 998	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
Delta	CheapestC$ 552	AverageC$ 695	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights
United Airlines	CheapestC$ 567	AverageC$ 754	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

Fly with Cheapflights

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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Cheap flights from Winnipeg to Chicago from C$ 210

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.

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

Cheap flight deals from Winnipeg to Chicago

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 27 February 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 27 February 2025.

Find flights from Winnipeg to Chicago within your budget

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 25 February 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 27 February 2025.

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.

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 27 February 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

Get a feel of what it's like to fly with Delta, Porter Airlines 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.

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?

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.

Alternative routes for Winnipeg to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Winnipeg to Chicago

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.

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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 27 February 2025.