HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$105+ Cheap flights from Illinois to Winnipeg (YWG)

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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Winnipeg 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.

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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$216
(Justfly.com)

One-way from

$105
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$635

Good round-trip deal

$573 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
Search Deals
From Illinois to Winnipeg
Search Deals
One-way flight from Illinois to Winnipeg
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 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
Price to beat on a one-way 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 March 31, 2025.

This Justfly.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/315:30 pmORD - YWG
1 stop18h 11mWestJet
Tue 6/108:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 3/30$216
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1411:10 amORD - YWG
2 stops13h 21mMultiple Airlines
Wed 5/218:30 amYWG - ORD
1 stop8h 14mMultiple Airlines
Deal found 3/30$257
This Gotogate deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/149:17 pmORD - YWG
1 stop15h 52mAir Canada
Wed 5/212:20 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 3/29$428
This Mytrip deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:50 amSTL - YWG
3 stops14h 23mMultiple Airlines
Sat 5/318:30 amYWG - STL
3 stops27h 40mMultiple Airlines
Deal found 3/30$429
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:30 amMDW - YWG
1 stop7h 58mMultiple Airlines
Sun 5/1112:52 pmYWG - MDW
1 stop4h 53mMultiple Airlines
Deal found 3/30$437
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:00 amMDW - YWG
2 stops17h 25mDelta
Wed 6/186:45 amYWG - MDW
2 stops14h 53mDelta
Deal found 3/30$447
This United deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:58 pmORD - YWG
Nonstop2h 35mUnited Airlines
Tue 6/102:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 3/30$509
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:05 amORD - YWG
2 stops16h 20mDelta
Sat 6/146:45 amYWG - ORD
2 stops6h 04mDelta
Deal found 3/30$514
This Agoda.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Agoda.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/139:20 amMDW - YWG
1 stop10h 48mWestJet
Thu 8/218:50 amYWG - MDW
1 stop4h 12mWestJet
Deal found 3/29$574
This Porter Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/49:40 amMDW - YWG
2 stops24h 46mPorter Airlines
Tue 6/1711:45 amYWG - MDW
2 stops21h 00mPorter Airlines
Deal found 3/30$596
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:00 amSTL - YWG
1 stop10h 28mDelta
Fri 6/139:00 amYWG - STL
1 stop8h 59mDelta
Deal found 3/30$621
This Justfly.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/139:00 amSTL - YWG
1 stop7h 23mWestJet
Tue 8/199:00 amYWG - STL
1 stop6h 58mWestJet
Deal found 3/30$690

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 2,558,603 searches. Data last updated March 31, 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 5/31

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Tue 6/10

8:30 am-4:44 pm

1 stop8h 14m

$216

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/14

11:10 am-12:31 am

2 stops13h 21m

Winnipeg

Wed 5/21

8:30 am-4:44 pm

1 stop8h 14m

$257

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/14

9:17 pm-1:09 pm

1 stop15h 52m

Winnipeg

Wed 5/21

2:20 pm-4:48 pm

Nonstop2h 28m

$428

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 5/13

9:50 am-12:13 am

3 stops14h 23m

Winnipeg

Sat 5/31

8:30 am-12:10 pm

3 stops27h 40m

$429

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/8

8:30 am-4:28 pm

1 stop7h 58m

Winnipeg

Sun 5/11

12:52 pm-5:45 pm

1 stop4h 53m

$437

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/31

6:00 am-11:25 pm

2 stops17h 25m

Winnipeg

Wed 6/18

6:45 am-9:38 pm

2 stops14h 53m

$447

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/31

7:58 pm-10:33 pm

Nonstop2h 35m

Winnipeg

Sun 6/15

2:20 pm-4:51 pm

Nonstop2h 31m

$509

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/31

7:05 am-11:25 pm

2 stops16h 20m

Winnipeg

Sat 6/14

6:45 am-12:49 pm

2 stops6h 04m

$514

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 8/13

9:20 am-8:08 pm

1 stop10h 48m

Winnipeg

Thu 8/21

8:50 am-1:02 pm

1 stop4h 12m

$574

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/4

9:40 am-10:26 am

2 stops24h 46m

Winnipeg

Tue 6/17

11:45 am-8:45 am

2 stops21h 00m

$596

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in April is currently the most expensive (average of $506). 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 March 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Winnipeg as you normally would.

Weekly flight availability from Illinois to Winnipeg

Explore weekly flight availability from Illinois to Winnipeg. 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 March 31, 2025.

The most flights from USIL to YWG 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 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 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 March 31, 2025.
Read reviews from past customers who have flown Delta, Porter Airlines and United Airlines from Illinois to Winnipeg. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

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
7,899 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

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
8,614 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

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
2,789 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

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
9,001 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

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?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Illinois. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

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

    $105 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $184 and $231, respectively.

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

    While some choose either Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg, Chicago O'Hare Intl - Winnipeg is the most popular route from Illinois to Winnipeg.

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

    Consider SkyWest Airlines (80%), Air Canada (80%) or United Airlines (80%) when booking your flight. These represent the most reliable airlines when flying from Illinois to Winnipeg.

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay $409 for a flight from Illinois to Winnipeg. The cheapest flight overall is $157 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $242.

  • 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, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in April is currently the most expensive (average of $506). 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

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.
O'Hare Intl to Winnipeg flights
Minneapolis to Winnipeg flights
John F Kennedy Intl to Winnipeg flights
Newark to Winnipeg flights
Los Angeles to Winnipeg flights
Denver to Winnipeg flights
LaGuardia to Winnipeg flights
Atlanta to Winnipeg flights
Dulles Intl to Winnipeg flights
Seattle to Winnipeg flights
San Francisco to Winnipeg flights
Hobby to Winnipeg flights
Detroit to Winnipeg flights
Baltimore to Winnipeg flights
Reagan-National to Winnipeg flights
Dallas/Fort Worth to Winnipeg flights
George Bush Intcntl to Winnipeg flights
Philadelphia to Winnipeg flights
Midway to Winnipeg flights
Boston to Winnipeg flights
Ontario to Winnipeg flights
San Diego to Winnipeg flights
Love Field to Winnipeg flights
Austin to Winnipeg flights
St. Louis to Winnipeg flights
Sky Harbor Intl to Winnipeg flights
Cleveland to Winnipeg flights
Orlando to Winnipeg flights
Charlotte to Winnipeg flights
Nashville to Winnipeg flights
Sacramento to Winnipeg flights
Portland to Winnipeg flights
Santa Ana to Winnipeg flights
Richmond to Winnipeg flights
Burbank to Winnipeg flights
Tampa to Winnipeg flights
Fort Lauderdale to Winnipeg flights
Raleigh to Winnipeg flights
Las Vegas to Winnipeg flights
Fort Myers to Winnipeg flights
Des Moines to Winnipeg flights
Duluth to Winnipeg flights
San Antonio to Winnipeg flights
Cincinnati to Winnipeg flights
Milwaukee to Winnipeg flights
Allentown to Winnipeg flights
Oakland to Winnipeg flights
Columbus to Winnipeg flights
San Jose to Winnipeg flights
Wichita to Winnipeg flights

Top 2 airlines flying from Illinois to Winnipeg

Discover the top 2 airlines 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 2,558,603 searches. Data last updated March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$232Average$617FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$535Average$666FlexibilityNo cancel feeOn-time69%
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.