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

WestJet, at C$ 328, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. WestJet is priced at 47% 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$ 232. However, be on the lookout for offers from United Airlines and Delta, 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$ 207. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 386 on average our data indicates C$ 1,212 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: Avianca (90%), Air Canada (89%), Air New Zealand( 89%).

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

Air Canada, United Airlines and WestJet 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 23%.

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

Find a great deal and save up to 19% 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$ 391.

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$ 627. You can even find prices in June for less than C$ 627, as users have found deals to Chicago from as low as C$ 260. The month of April 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 7 flights from Winnipeg to Chicago per day from 3 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$ 208+ Flights from Winnipeg to Chicago

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

Cheap flight deals from Winnipeg to Chicago

Round-trip from	C$ 328
One-way from	C$ 208
Popular in	April
Cheapest in	June
Average price	C$ 558
Good round-trip deal	C$ 565 or less
Good one-way deal	C$ 432 or less

WestJet
3/10-5/10
2 total stops
15h 58m total
Winnipeg to Chicago

Search Deals

1/8
1 total stop
12h 30m total
Winnipeg to Chicago

Search Deals

Highest demand for flights based on searches. 0% potential increase in price (C$ 2 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 June 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 12 June 2025.

Fri 3/108:30 a.m.YWG - ORD

1 stop8h 13mWestJet

Sun 5/101:40 p.m.ORD - YWG

1 stop7h 45mWestJet

Deal found 10/6C$ 328

Mon 23/69:00 a.m.YWG - ORD

1 stop24h 38mMultiple Airlines

Mon 30/610:43 a.m.ORD - YWG

2 stops32h 41mMultiple Airlines

Deal found 9/6C$ 416

Fri 19/912:40 p.m.YWG - MDW

1 stop5h 27mDelta

Tue 23/91:00 p.m.MDW - YWG

2 stops10h 32mDelta

Deal found 11/6C$ 619

Thu 28/82:20 p.m.YWG - ORD

Nonstop2h 31mUnited Airlines

Tue 2/97:15 a.m.ORD - YWG

1 stop5h 54mUnited Airlines

Deal found 10/6C$ 619

Wed 6/85:00 a.m.YWG - ORD

1 stop8h 13mAir Canada

Sun 10/89:55 a.m.ORD - YWG

1 stop6h 23mAir Canada

Deal found 12/6C$ 638

Sat 2/88:35 a.m.YWG - ORD

1 stop8h 15mDelta

Sat 9/86:00 a.m.ORD - YWG

1 stop5h 31mDelta

Deal found 10/6C$ 659

Fri 25/79:00 a.m.YWG - MDW

1 stop12h 42mWestJet

Mon 28/76:20 p.m.MDW - YWG

2 stops19h 23mWestJet

Deal found 10/6C$ 669

Mon 23/611:45 a.m.YWG - MDW

2 stops21h 00mPorter Airlines

Mon 30/65:50 p.m.MDW - YWG

2 stops28h 56mPorter Airlines

Deal found 9/6C$ 680

Sun 24/811:45 a.m.YWG - MDW

2 stops28h 39mMultiple Airlines

Sun 31/89:40 a.m.MDW - YWG

2 stops13h 06mMultiple Airlines

Deal found 12/6C$ 781

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 12 June 2025.

Fri 3/108:30 a.m.YWG - ORD

1 stop8h 13mWestJet

Sun 5/101:40 p.m.ORD - YWG

1 stop7h 45mWestJet

Deal found 10/6C$ 328

Mon 23/69:00 a.m.YWG - ORD

1 stop24h 38mMultiple Airlines

Mon 30/610:43 a.m.ORD - YWG

2 stops32h 41mMultiple Airlines

Deal found 9/6C$ 416

Fri 19/912:40 p.m.YWG - MDW

1 stop5h 27mDelta

Tue 23/91:00 p.m.MDW - YWG

2 stops10h 32mDelta

Deal found 11/6C$ 619

Thu 28/82:20 p.m.YWG - ORD

Nonstop2h 31mUnited Airlines

Tue 2/97:15 a.m.ORD - YWG

1 stop5h 54mUnited Airlines

Deal found 10/6C$ 619

Wed 6/85:00 a.m.YWG - ORD

1 stop8h 13mAir Canada

Sun 10/89:55 a.m.ORD - YWG

1 stop6h 23mAir Canada

Deal found 12/6C$ 638

Mon 23/611:45 a.m.YWG - MDW

2 stops21h 00mPorter Airlines

Mon 30/65:50 p.m.MDW - YWG

2 stops28h 56mPorter Airlines

Deal found 9/6C$ 680

Sat 2/88:35 a.m.YWG - ORD

1 stop8h 15mDelta

Sat 9/86:00 a.m.ORD - YWG

1 stop5h 31mDelta

Deal found 10/6C$ 659

Fri 25/79:00 a.m.YWG - MDW

1 stop12h 42mWestJet

Mon 28/76:20 p.m.MDW - YWG

2 stops19h 23mWestJet

Deal found 10/6C$ 669

Sun 24/811:45 a.m.YWG - MDW

2 stops28h 39mMultiple Airlines

Sun 31/89:40 a.m.MDW - YWG

2 stops13h 06mMultiple Airlines

Deal found 12/6C$ 781

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 12 June 2025.

Fri 19/92:20 p.m.YWG - ORD

Nonstop2h 31mUnited Airlines

Tue 23/97:54 p.m.ORD - YWG

Nonstop2h 39mUnited Airlines

Deal found 10/6C$ 619

Thu 28/82:20 p.m.YWG - ORD

Nonstop2h 31mMultiple Airlines

Tue 2/91:01 p.m.ORD - YWG

Nonstop2h 30mMultiple Airlines

Deal found 10/6C$ 850

Fri 18/77:00 a.m.YWG - ORD

Nonstop2h 31mAir Canada

Sat 19/77:58 p.m.ORD - YWG

Nonstop2h 35mAir Canada

Deal found 11/6C$ 896

Last-minute flights from Winnipeg to Chicago
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated 12 June 2025 and is based on user searches.

Sat 21/63:15 p.m.YWG - ORD

2 stops14h 57mMultiple Airlines

Tue 24/610:15 p.m.ORD - YWG

3 stops25h 27mMultiple Airlines

Deal found 11/6C$ 648

Sat 21/66:45 a.m.YWG - ORD

1 stop10h 04mWestJet

Tue 24/68:17 p.m.ORD - YWG

1 stop20h 35mWestJet

Deal found 11/6C$ 882

Sat 21/66:30 a.m.YWG - MDW

2 stops12h 11mWestJet

Tue 24/69:21 a.m.MDW - YWG

2 stops10h 55mWestJet

Deal found 11/6C$ 886

Sat 21/65:00 a.m.YWG - ORD

2 stops13h 28mUnited Airlines

Tue 24/67:58 p.m.ORD - YWG

Nonstop2h 35mUnited Airlines

Deal found 11/6C$ 913

Sat 21/66:15 a.m.YWG - ORD

1 stop6h 48mAir Canada

Tue 24/67:58 p.m.ORD - YWG

Nonstop2h 35mAir Canada

Deal found 11/6C$ 924

Mon 23/69:00 a.m.YWG - ORD

1 stop24h 38mMultiple Airlines

Mon 30/610:43 a.m.ORD - YWG

2 stops32h 41mMultiple Airlines

Deal found 9/6C$ 416

Mon 23/611:45 a.m.YWG - MDW

2 stops21h 00mPorter Airlines

Mon 30/65:50 p.m.MDW - YWG

2 stops28h 56mPorter Airlines

Deal found 9/6C$ 680

Fri 4/76:45 a.m.YWG - ORD

1 stop8h 19mDelta

Sun 6/76:00 a.m.ORD - YWG

1 stop5h 36mDelta

Deal found 11/6C$ 690

Wed 9/712:26 p.m.YWG - MDW

1 stop5h 13mDelta

Sat 12/79:24 a.m.MDW - YWG

1 stop7h 26mDelta

Deal found 10/6C$ 727

Wed 9/712:26 p.m.YWG - MDW

1 stop5h 13mMultiple Airlines

Mon 14/75:20 p.m.MDW - YWG

2 stops29h 26mMultiple Airlines

Deal found 12/6C$ 829

Sat 12/77:00 a.m.YWG - ORD

Nonstop2h 31mUnited Airlines

Wed 16/75:00 a.m.ORD - YWG

1 stop8h 09mUnited Airlines

Deal found 10/6C$ 619

Fri 18/76:35 p.m.YWG - ORD

1 stop14h 34mAir Canada

Sat 19/73:50 p.m.ORD - YWG

1 stop7h 38mAir Canada

Deal found 12/6C$ 669

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 12 June 2025.

Fri 1/89:00 a.m.YWG - ORD

1 stop12h 30mMultiple Airlines

Deal found 12/6C$ 208

Fri 1/89:00 a.m.YWG - MDW

1 stop14h 17mMultiple Airlines

Deal found 12/6C$ 231

Wed 13/88:30 a.m.YWG - ORD

1 stop8h 14mWestJet

Deal found 10/6C$ 232

Sat 12/72:20 p.m.YWG - ORD

Nonstop2h 31mUnited Airlines

Deal found 11/6C$ 343

Fri 1/85:42 p.m.YWG - ORD

1 stop3h 52mDelta

Deal found 10/6C$ 351

Wed 9/75:00 a.m.YWG - ORD

1 stop8h 13mAir Canada

Deal found 11/6C$ 372

Fri 25/78:35 a.m.YWG - MDW

1 stop9h 04mDelta

Deal found 10/6C$ 383

Fri 1/89:00 a.m.YWG - MDW

1 stop12h 42mWestJet

Deal found 10/6C$ 388

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

Fri 3/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 5/10

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 328

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 23/6

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

1 stop24h 38m

Chicago O'Hare Intl

Mon 30/6

10:43 a.m.-7:24 p.m.

2 stops32h 41m

C$ 416

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 19/9

12:40 p.m.-6:07 p.m.

1 stop5h 27m

Chicago Midway

Tue 23/9

1:00 p.m.-11:32 p.m.

2 stops10h 32m

C$ 619

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 28/8

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

Nonstop2h 31m

Chicago O'Hare Intl

Tue 2/9

7:15 a.m.-1:09 p.m.

1 stop5h 54m

C$ 619

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 6/8

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/8

9:55 a.m.-4:18 p.m.

1 stop6h 23m

C$ 638

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 2/8

8:35 a.m.-4:50 p.m.

1 stop8h 15m

Chicago O'Hare Intl

Sat 9/8

6:00 a.m.-11:31 a.m.

1 stop5h 31m

C$ 659

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 25/7

9:00 a.m.-9:42 p.m.

1 stop12h 42m

Chicago Midway

Mon 28/7

6:20 p.m.-1:43 p.m.

2 stops19h 23m

C$ 669

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 23/6

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

2 stops21h 00m

Chicago Midway

Mon 30/6

5:50 p.m.-10:46 p.m.

2 stops28h 56m

C$ 680

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 24/8

11:45 a.m.-4:24 p.m.

2 stops28h 39m

Chicago Midway

Sun 31/8

9:40 a.m.-10:46 p.m.

2 stops13h 06m

C$ 781

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/8

9:00 a.m.-9:30 p.m.

1 stop12h 30m

C$ 208

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 17 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.

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 best time to book flights from Winnipeg to Chicago is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in March is currently the most expensive (average of C$ 352). 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 15% 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. Sunday 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 (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 Porter Airlines, Delta and United Airlines from Winnipeg to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Porter Airlines

8.0

Very good

288 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Delta

8.0

Very good

7,950 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

United Airlines

7.4

Good

8,790 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

WestJet

7.2

Good

2,868 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Air Canada

7.1

Good

9,531 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

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 7 flights from Winnipeg to Chicago per day from 3 different airlines.
What are the cheapest airlines flying from Winnipeg to Chicago round-trip?
WestJet, at C$ 328, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. WestJet is priced at 47% 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$ 232. However, be on the lookout for offers from United Airlines 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?
Before booking your flight to Chicago from Winnipeg, check out the most reliable airlines to get you to your destination on time: Avianca (90%), Air Canada (89%), Air New Zealand( 89%).
What are the cheapest flights from Winnipeg to Chicago?
Looking at all options, your cheapest flight can be booked for C$ 207. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 386 on average our data indicates C$ 1,212 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$ 352). 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 3 airlines flying from Winnipeg to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 198	AverageC$ 477	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
Air Canada	CheapestC$ 375	AverageC$ 642	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
United Airlines	CheapestC$ 539	AverageC$ 679	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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Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

Cheap flights from Winnipeg to Chicago from C$ 208

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel.

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

Cheap flight deals from Winnipeg to Chicago

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 12 June 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 12 June 2025.

Cheapflights Fare Finder

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

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 9 June 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 12 June 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 12 June 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 Porter Airlines, Delta and United Airlines from Winnipeg to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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 3 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.

How does Cheapflights help users find flights from Winnipeg to Chicago?

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Chicago?

Can Cheapflights find flights from Winnipeg to Chicago with no change fees?

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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 12 June 2025.