Sign in
Cheap flights from Illinois to Winnipeg from C$ 251
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
11 Nov — 18 Nov1
Cheap flight deals from Illinois to Winnipeg
Enter your travel dates to find the best prices.
Cheapest
Best
Direct
Last-minute
One-way
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 12 October 2026.
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 12 October 2026.
Mon 14/128:15 a.m. -
2 stops16h 55m
Wed 16/127:00 a.m. -
1 stop11h 37m
Deal found 8/10C$ 570
Wed 28/107:28 p.m. -
2 stops21h 57m
Thu 29/109:35 p.m. -
2 stops21h 10m
Deal found 9/10C$ 646
Thu 26/117:49 a.m. -
2 stops17h 21m
Sun 29/117:55 p.m. -
1 stop21h 45m
Deal found 11/10C$ 671
Mon 2/117:50 p.m. -
2 stops21h 35m
Tue 3/119:35 p.m. -
2 stops20h 55m
Deal found 9/10C$ 674
Sun 20/128:10 a.m. -
1 stop30h 30m
Sun 10/19:35 p.m. -
2 stops25h 48m
Deal found 9/10C$ 680
Sun 20/128:10 a.m. -
1 stop30h 30m
Mon 11/17:00 a.m. -
1 stop16h 23m
Deal found 9/10C$ 683
Fri 6/116:20 p.m. -
1 stop15h 55m
Mon 9/117:55 p.m. -
1 stop15h 40m
Deal found 7/10C$ 694
Tue 15/1212:15 p.m. -
1 stop9h 42m
Wed 16/127:00 a.m. -
1 stop11h 37m
Deal found 8/10C$ 717
Sun 20/128:10 a.m. -
1 stop30h 30m
Sat 9/19:35 p.m. -
2 stops14h 15m
Deal found 9/10C$ 738
Thu 10/128:15 a.m. -
2 stops16h 55m
Sat 12/127:00 a.m. -
1 stop10h 40m
Deal found 8/10C$ 754
Best flights from Illinois to WinnipegDiscover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 October 2026.
Discover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 October 2026.
Thu 26/117:49 a.m. -
2 stops17h 21m
Sun 29/117:55 p.m. -
1 stop21h 45m
Deal found 11/10C$ 671
Tue 24/116:20 p.m. -
2 stops23h 46m
Tue 1/127:00 a.m. -
1 stop7h 36m
Deal found 10/10C$ 1,022
Thu 26/114:30 p.m. -
1 stop8h 14m
Sun 29/113:15 p.m. -
Nonstop1h 35m
Deal found 11/10C$ 1,179
Fri 6/116:20 p.m. -
1 stop15h 55m
Mon 9/117:55 p.m. -
1 stop15h 40m
Deal found 7/10C$ 694
Fri 6/1112:15 p.m. -
2 stops29h 51m
Mon 9/1111:35 a.m. -
2 stops30h 05m
Deal found 7/10C$ 1,062
Wed 28/102:50 p.m. -
1 stop7h 07m
Sat 7/117:00 a.m. -
1 stop7h 37m
Deal found 10/10C$ 1,155
Fri 6/119:35 a.m. -
Nonstop2h 48m
Mon 9/112:15 p.m. -
Nonstop2h 35m
Deal found 7/10C$ 1,290
Fri 30/102:50 p.m. -
1 stop7h 07m
Sun 8/117:00 a.m. -
1 stop7h 37m
Deal found 10/10C$ 1,267
Direct flights from Illinois to WinnipegExplore direct flight options from Illinois to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 12 October 2026.
Explore direct flight options from Illinois to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 12 October 2026.
Fri 6/119:35 a.m. -
Nonstop2h 48m
Mon 9/112:15 p.m. -
Nonstop2h 35m
Deal found 7/10C$ 1,290
Thu 22/1010:00 a.m. -
Nonstop2h 37m
Thu 12/112:15 p.m. -
Nonstop2h 35m
Deal found 8/10C$ 1,313
Wed 11/119:35 a.m. -
Nonstop2h 48m
Mon 16/112:15 p.m. -
Nonstop2h 35m
Deal found 8/10C$ 1,314
Wed 4/119:35 a.m. -
Nonstop3h 48m
Wed 11/113:15 p.m. -
Nonstop1h 35m
Deal found 9/10C$ 1,350
Thu 10/129:35 a.m. -
Nonstop2h 48m
Sat 12/122:15 p.m. -
Nonstop2h 45m
Deal found 8/10C$ 1,351
Tue 10/119:35 a.m. -
Nonstop3h 48m
Tue 17/113:15 p.m. -
Nonstop1h 35m
Deal found 11/10C$ 1,353
Mon 8/33:50 p.m. -
Nonstop2h 51m
Tue 9/37:00 a.m. -
Nonstop2h 31m
Deal found 8/10C$ 1,380
Wed 28/109:29 a.m. -
Nonstop2h 54m
Mon 2/112:15 p.m. -
Nonstop2h 35m
Deal found 8/10C$ 1,388
Last-minute flights from Illinois to WinnipegDiscover last-minute flight deals from Illinois to Winnipeg. Data last updated 12 October 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Winnipeg. Data last updated 12 October 2026 and is based on user searches.
Wed 28/107:28 p.m. -
2 stops21h 57m
Thu 29/109:35 p.m. -
2 stops21h 10m
Deal found 9/10C$ 646
Mon 2/117:50 p.m. -
2 stops21h 35m
Tue 3/119:35 p.m. -
2 stops20h 55m
Deal found 9/10C$ 674
Thu 5/117:50 p.m. -
2 stops29h 20m
Thu 12/1110:00 a.m. -
2 stops8h 35m
Deal found 11/10C$ 808
Fri 6/116:20 p.m. -
1 stop15h 55m
Mon 9/117:55 p.m. -
1 stop15h 40m
Deal found 7/10C$ 694
Tue 10/117:35 p.m. -
2 stops29h 35m
Tue 17/119:35 p.m. -
3 stops19h 32m
Deal found 11/10C$ 770
Thu 26/117:49 a.m. -
2 stops17h 21m
Sun 29/117:55 p.m. -
1 stop21h 45m
Deal found 11/10C$ 671
Mon 30/1112:15 p.m. -
1 stop9h 37m
Fri 1/17:00 a.m. -
1 stop13h 16m
Deal found 8/10C$ 788
One-way flights from Illinois to WinnipegSearch for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 12 October 2026.
Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 12 October 2026.
Tue 2/26:00 a.m. -
2 stops19h 10m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/10C$ 251
Sat 30/16:00 a.m. -
2 stops35h 25m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/10C$ 252
Tue 17/117:35 p.m. -
2 stops21h 50m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 9/10C$ 262
Mon 18/16:00 a.m. -
1 stop8h 40m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 11/10C$ 277
Wed 3/210:18 a.m. -
3 stops31h 07m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/10C$ 278
Mon 1/26:00 a.m. -
1 stop8h 40m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/10C$ 282
Thu 4/25:32 p.m. -
1 stop21h 08m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/10C$ 288
Wed 18/117:35 p.m. -
2 stops21h 50m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 9/10C$ 292
Thu 26/117:49 a.m. -
2 stops17h 21m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 12/10C$ 301
Find flight deals from Illinois to Winnipeg
Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 12 October 2026.
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 7,457,451 searches. Data last updated 12 October 2026.
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
Cheapest round-trip
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 18/1
6:00 a.m.-2:40 p.m.
1 stop8h 40m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 277
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 4/2
5:32 p.m.-2:40 p.m.
1 stop21h 08m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 288
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 26/11
7:49 a.m.-1:10 a.m.
2 stops17h 21m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 301
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 9/11
7:50 p.m.-5:25 p.m.
2 stops21h 35m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 322
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sun 8/11
6:00 a.m.-11:55 p.m.
3 stops17h 55m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 361
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 21/11
2:50 p.m.-10:15 a.m.
1 stop19h 25m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 446
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 19/11
2:50 p.m.-9:52 p.m.
1 stop7h 02m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 458
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 18/11
2:50 p.m.-9:52 p.m.
1 stop7h 02m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 458
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 19/11
10:19 a.m.-10:15 a.m.
3 stops23h 56m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 465
Quickest round-trip
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 21/11
9:35 a.m.-12:23 p.m.
Nonstop2h 48m
Winnipeg
Wed 31/12
12:00 a.m.-12:00 a.m.
Nonstop0h 00m
C$ 609
Showing 1-10 of 18 resultsSorted by cheapest first
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.
ORD-YWG
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
USIL-YWG
ORD-YWG
What is the cheapest month to book a flight from Illinois to Winnipeg?
Currently, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 730). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,755). 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 12 October 2026.
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 12 October 2026.
The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
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 Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsSelkirk
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
Complete your trip
Direct flights to Manitoba
Flights by cabin class
Other flight options
Popular flights
Winnipeg flight routes
Alternative routes for Illinois to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Direct flights to Manitoba
Book a non-stop flight to one of these other cities located in Manitoba.
Search flights from Illinois to Winnipeg by cabin class
Find flights from Illinois to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Winnipeg flights
Browse other Illinois and Winnipeg flight options. Last updated on 12 October 2026.
Popular flight searches
Check out other popular destinations found by fellow travellers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 12 October 2026.
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.