Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Illinois to Winnipeg from C$ 219

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
2 Apr — 9 Apr1
1 adult

Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 28 March 2025.

Round-trip from

C$ 364

One-way from

C$ 219

Popular in

February

Cheapest in

January

Average price

C$ 908

Good round-trip deal

C$ 458 or less
WestJet
  • WestJet
  • 31/5-10/6
  • 2 total stops
  • 26h 25m total
  • Illinois to Winnipeg
Search Deals
11/5
  • 11/5
  • 2 total stops
  • 14h 31m total
  • Illinois to Winnipeg
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Winnipeg.
Search Deals

Find flight deals from Illinois to Winnipeg

Cheapest flights from Illinois to Winnipeg
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 March 2025.

Sat 31/55:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Tue 10/68:30 a.m.YWG - ORD
1 stop8h 14mWestJet
Deal found 27/3C$ 364
Mon 12/56:20 a.m.ORD - YWG
1 stop10h 08mMultiple Airlines
Mon 19/59:00 a.m.YWG - ORD
1 stop7h 25mMultiple Airlines
Deal found 27/3C$ 407
Mon 12/58:30 a.m.MDW - YWG
1 stop7h 58mMultiple Airlines
Mon 19/56:30 a.m.YWG - MDW
2 stops12h 38mMultiple Airlines
Deal found 28/3C$ 440
Sun 11/512:57 p.m.ORD - YWG
Nonstop2h 34mAir Canada
Sun 18/52:20 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Deal found 27/3C$ 607
Sun 11/510:10 a.m.STL - YWG
2 stops30h 18mMultiple Airlines
Sun 18/57:45 a.m.YWG - STL
3 stops36h 25mMultiple Airlines
Deal found 27/3C$ 657
Sat 28/67:58 p.m.ORD - YWG
Nonstop2h 35mUnited Airlines
Thu 17/77:00 a.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 26/3C$ 728
Sun 11/51:55 p.m.MDW - YWG
1 stop6h 13mDelta
Sun 18/58:30 a.m.YWG - MDW
1 stop4h 45mDelta
Deal found 27/3C$ 763
Sun 26/105:20 p.m.ORD - YWG
1 stop6h 02mDelta
Sat 1/116:40 a.m.YWG - ORD
2 stops5h 58mDelta
Deal found 27/3C$ 776
Tue 1/79:40 a.m.MDW - YWG
2 stops13h 06mPorter Airlines
Tue 15/711:45 a.m.YWG - MDW
2 stops28h 39mPorter Airlines
Deal found 26/3C$ 829
Sun 11/57:30 a.m.STL - YWG
1 stop6h 32mAir Canada
Sun 18/511:00 a.m.YWG - STL
1 stop8h 58mAir Canada
Deal found 27/3C$ 852
Tue 28/102:00 p.m.MDW - YWG
2 stops33h 20mWestJet
Fri 7/117:30 a.m.YWG - MDW
1 stop26h 21mWestJet
Deal found 27/3C$ 878
Thu 5/66:00 a.m.STL - YWG
1 stop10h 28mDelta
Fri 13/69:00 a.m.YWG - STL
1 stop8h 59mDelta
Deal found 27/3C$ 908

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 28 March 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 31/5

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Tue 10/6

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

1 stop8h 14m

C$ 364

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 1/7

6:00 a.m.-4:23 p.m.

1 stop10h 23m

Winnipeg

Mon 28/7

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

1 stop8h 14m

C$ 414

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 11/5

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

Nonstop2h 34m

Winnipeg

Sun 18/5

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

Nonstop2h 28m

C$ 607

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 11/5

10:10 a.m.-4:28 p.m.

2 stops30h 18m

Winnipeg

Sun 18/5

7:45 a.m.-8:10 p.m.

3 stops36h 25m

C$ 657

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 28/6

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

Winnipeg

Fri 18/7

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

Nonstop2h 31m

C$ 728

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 1/7

9:40 a.m.-6:00 p.m.

1 stop8h 20m

Winnipeg

Tue 15/7

6:55 p.m.-8:45 a.m.

1 stop13h 50m

C$ 748

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 11/5

1:55 p.m.-8:08 p.m.

1 stop6h 13m

Winnipeg

Sun 18/5

8:30 a.m.-1:15 p.m.

1 stop4h 45m

C$ 763

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 1/7

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

2 stops13h 06m

Winnipeg

Tue 15/7

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

2 stops28h 39m

C$ 829

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 1/7

2:00 p.m.-11:29 p.m.

2 stops9h 29m

Winnipeg

Tue 8/7

8:50 a.m.-6:40 p.m.

2 stops9h 50m

C$ 830

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 11/5

7:30 a.m.-2:02 p.m.

1 stop6h 32m

Winnipeg

Sun 18/5

11:00 a.m.-7:58 p.m.

1 stop8h 58m

C$ 852

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/3

Showing 1-10 of 23 results
1
2
3

Best time to book a flight from Illinois to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Illinois 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 Illinois to Winnipeg

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 232). 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 IL to YWG?

Find hourly flight availability from Illinois to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 March 2025.

When flying from Illinois to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Winnipeg by month

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

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

Temperature in Winnipeg by month

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

If weather is an important factor for your trip to Winnipeg, 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 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated 28 March 2025.
See what other customers who have flown with Delta, Porter Airlines and United Airlines from Illinois to Winnipeg have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
8,981 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Comfort

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Winnipeg. 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 into for flights to Winnipeg from Illinois?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly into when you book flights from Illinois to Winnipeg.

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

    One-way options have recently been found by users for as low as C$ 334 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 343 and Delta from C$ 390 one-way.

  • What are the most popular routes from Illinois to Winnipeg?

    The most popular route from Illinois to Winnipeg is Chicago O'Hare Intl - Winnipeg. You may also consider Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg.

  • What are the most reliable airlines from Illinois to Winnipeg?

    The top 3 most reliable airlines when flying from Illinois to Winnipeg are SkyWest Airlines (80%), Air Canada (80%) and United Airlines (80%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 459 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 305 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 402.

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

    Yes. In addition to deals on Illinois to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Winnipeg.

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

    Yes. Cheapflights offers flight deals from Illinois to Winnipeg 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 Illinois to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 232). 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

Travelling to a place near Illinois?

Book flights to Illinois if you plan to visit one of these locations
Portage la Prairie

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 Illinois to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Winnipeg flights
Newark to Winnipeg flights
LaGuardia to Winnipeg flights
O'Hare Intl to Winnipeg flights
Los Angeles to Winnipeg flights
Dulles Intl to Winnipeg flights
Minneapolis to Winnipeg flights
Baltimore to Winnipeg flights
Reagan-National to Winnipeg flights
Hobby to Winnipeg flights
Denver to Winnipeg flights
Atlanta to Winnipeg flights
Dallas/Fort Worth to Winnipeg flights
Ontario to Winnipeg flights
Boston to Winnipeg flights
Detroit to Winnipeg flights
George Bush Intcntl to Winnipeg flights
Philadelphia to Winnipeg flights
San Francisco to Winnipeg flights
Seattle to Winnipeg flights
Charlotte to Winnipeg flights
Cleveland to Winnipeg flights
St. Louis to Winnipeg flights
Sacramento to Winnipeg flights
Tampa to Winnipeg flights
Orlando to Winnipeg flights
Fort Lauderdale to Winnipeg flights
Columbus to Winnipeg flights
Duluth to Winnipeg flights
San Antonio to Winnipeg flights
Milwaukee to Winnipeg flights
Sky Harbor Intl to Winnipeg flights
San Jose to Winnipeg flights
Cincinnati to Winnipeg flights
Richmond to Winnipeg flights
Fort Myers to Winnipeg flights
Santa Ana to Winnipeg flights
Portland to Winnipeg flights
San Diego to Winnipeg flights
Hartford to Winnipeg flights
Oakland to Winnipeg flights
Austin to Winnipeg flights
Madison to Winnipeg flights
Salt Lake City to Winnipeg flights
Columbia to Winnipeg flights
Fargo to Winnipeg flights

Top airline flying from Illinois to Winnipeg

Discover the top airline that operate flights from Illinois to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 28 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 458AverageC$ 1,036FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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 Illinois to Winnipeg?

Cheapflights makes it easy to find Illinois to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

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 Winnipeg from Illinois.

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

Yes! Cheapflights helps users easily find flights from Illinois to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from Illinois to Winnipeg become cheaper?

Yes! Start tracking prices for Illinois to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
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.