Cheap flights from Illinois to Winnipeg from C$ 165
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 29/7. Fares are subject to change and may not be available on all flights or dates of travel.
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 3 July 2025.
Find flight deals from Illinois to Winnipeg
Cheapest flights from Illinois to WinnipegExplore 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 3 July 2025.
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 3 July 2025.
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 3 July 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Thu 16/10
5:30 p.m.-9:01 a.m.
1 stop15h 31m
Winnipeg
Fri 24/10
8:30 a.m.-4:43 p.m.
1 stop8h 13m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Wed 1/10
11:45 a.m.-12:30 a.m.
2 stops12h 45m
Winnipeg
Mon 13/10
9:00 a.m.-12:10 a.m.
1 stop15h 10m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fri 15/8
6:20 a.m.-4:23 p.m.
1 stop10h 03m
Winnipeg
Fri 22/8
6:00 a.m.-11:27 p.m.
2 stops17h 27m
St. LouisWinnipeg
STL - YWG
STLYWG
Lambert-St Louis
Wed 20/8
3:40 p.m.-4:23 p.m.
1 stop24h 43m
Winnipeg
Wed 3/9
6:30 a.m.-7:07 p.m.
2 stops12h 37m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fri 15/8
12:43 p.m.-12:31 a.m.
2 stops11h 48m
Winnipeg
Fri 22/8
8:15 p.m.-9:36 a.m.
2 stops13h 21m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Thu 21/8
9:15 a.m.-4:51 p.m.
1 stop7h 36m
Winnipeg
Sat 23/8
12:43 p.m.-5:37 p.m.
1 stop4h 54m
St. LouisWinnipeg
STL - YWG
STLYWG
Lambert-St Louis
Mon 22/9
5:30 p.m.-3:31 p.m.
1 stop22h 01m
Winnipeg
Mon 29/9
2:20 p.m.-2:27 p.m.
1 stop24h 07m
St. LouisWinnipeg
STL - YWG
STLYWG
Lambert-St Louis
Mon 18/8
1:30 p.m.-8:29 p.m.
1 stop6h 59m
Winnipeg
Mon 8/9
11:40 a.m.-7:57 p.m.
1 stop8h 17m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Tue 29/7
11:39 a.m.-9:31 p.m.
3 stops33h 52m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Wed 23/7
5:34 p.m.-9:31 p.m.
3 stops27h 57m
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.
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$ 231). 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 3 July 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.
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 3 July 2025.
The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).
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 3 July 2025.
See what other customers who have flown with Porter Airlines,Delta, andUnited Airlines from Illinois to Winnipeg have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Food
Crew
Comfort
Entertainment
Overall
Reviews
Mary,Jun 2025
FLL - YYZ
Boarding
Food
Crew
Comfort
Entertainment
Overall
Reviews
Mary,Jun 2025
FLL - YYZ
Boarding
Food
Crew
Comfort
Entertainment
Overall
Reviews
Mary,Jun 2025
FLL - YYZ
Boarding
Food
Crew
Comfort
Entertainment
Overall
Reviews
Mary,Jun 2025
FLL - YYZ
Boarding
Food
Crew
Comfort
Entertainment
Overall
Reviews
Mary,Jun 2025
FLL - YYZ
Boarding
Food
Crew
Comfort
Entertainment
Overall
Reviews
Mary,Jun 2025
FLL - YYZ
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.
Travelling to a place near Illinois?
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Alternative routes for Illinois to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.
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 3 July 2025.
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.