$176+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)
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.
CHI — YWG
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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 Chicago to Winnipeg
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Cheapest flights from Chicago to WinnipegExplore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 12/148:15 am -
2 stops16h 55m
Wed 12/167:00 am -
1 stop11h 37m
Deal found 10/8![Multiple Airlines logo]()
$400
This Mytrip deal was found by Cheapflights users on 10/6. 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 11/37:35 pm -
2 stops21h 50m
Tue 11/109:35 pm -
2 stops20h 55m
Deal found 10/6![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Tue 11/106:20 pm -
1 stop15h 55m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/5![Multiple Airlines logo]()
$419
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Mon 11/26:42 pm -
2 stops22h 43m
Tue 11/179:35 pm -
2 stops20h 12m
Deal found 10/6![Multiple Airlines logo]()
$419
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Mon 11/96:08 am -
2 stops19h 02m
Tue 11/179:35 pm -
2 stops20h 12m
Deal found 10/7![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Mon 11/212:15 pm -
1 stop22h 00m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/6![Multiple Airlines logo]()
$426
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Mon 11/97:50 pm -
2 stops29h 20m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/7![Multiple Airlines logo]()
$434
This Mytrip deal was found by Cheapflights users on 10/6. 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 11/36:16 am -
2 stops18h 54m
Tue 11/109:35 pm -
2 stops20h 12m
Deal found 10/6![Multiple Airlines logo]()
$449
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Fri 10/306:42 pm -
2 stops22h 43m
Sun 11/19:35 pm -
2 stops20h 12m
Deal found 10/7![Multiple Airlines logo]()
$451
This Mytrip deal was found by Cheapflights users on 10/9. 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.
Wed 10/287:28 pm -
2 stops21h 57m
Thu 10/299:35 pm -
2 stops21h 10m
Deal found 10/9![Multiple Airlines logo]()
$453
This Mytrip deal was found by Cheapflights users on 10/9. 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.
Wed 10/286:42 pm -
2 stops22h 43m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 10/9![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 10/225:30 pm -
1 stop7h 25m
Tue 10/279:35 pm -
2 stops15h 16m
Deal found 10/6![Multiple Airlines logo]()
$468
Best flights from Chicago to WinnipegDiscover carefully curated flight deals from Chicago to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
Discover carefully curated flight deals from Chicago to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This Mytrip deal was found by Cheapflights users on 10/5. 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 11/106:08 am -
2 stops29h 12m
Tue 11/179:35 pm -
2 stops20h 12m
Deal found 10/5![Multiple Airlines logo]()
$470
This Porter Airlines deal was found by Cheapflights users on 10/7. 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.
Sat 11/216:20 pm -
2 stops23h 46m
Sat 11/287:00 am -
1 stop7h 46m
Deal found 10/7![Porter Airlines logo]()
$714
This Delta deal was found by Cheapflights users on 10/5. 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.
Tue 11/101:31 pm -
2 stops11h 02m
Tue 11/171:45 pm -
1 stop2h 54m
Deal found 10/5![Delta logo]()
$793
This Air Canada deal was found by Cheapflights users on 10/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:00 am -
Nonstop2h 37m
Thu 11/122:15 pm -
Nonstop2h 35m
Deal found 10/5![Air Canada logo]()
$894
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:45 am -
1 stop8h 05m
Thu 11/127:00 am -
2 stops14h 29m
Deal found 10/5![American Airlines logo]()
$928
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/209:23 pm -
1 stop17h 17m
Mon 1/119:35 pm -
2 stops26h 11m
Deal found 10/9![Multiple Airlines logo]()
$511
This FlightHub deal was found by Cheapflights users on 10/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:27 pm -
1 stop10h 52m
Wed 10/289:35 pm -
2 stops12h 28m
Deal found 10/6![WestJet logo]()
$1,044
This Justfly.com deal was found by Cheapflights users on 10/10. 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 10/282:50 pm -
1 stop7h 07m
Mon 11/27:00 am -
1 stop7h 37m
Deal found 10/10![Porter Airlines logo]()
$721
This Mytrip deal was found by Cheapflights users on 10/5. 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.
Mon 11/27:50 pm -
2 stops21h 35m
Mon 11/94:00 pm -
1 stop13h 13m
Deal found 10/5![Multiple Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 10/7. 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.
Mon 11/912:30 pm -
1 stop5h 12m
Tue 11/176:35 am -
1 stop5h 15m
Deal found 10/7![Delta logo]()
$862
This Air Canada deal was found by Cheapflights users on 10/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:35 am -
Nonstop2h 48m
Sun 11/292:15 pm -
Nonstop2h 35m
Deal found 10/8![Air Canada logo]()
$922
This Delta deal was found by Cheapflights users on 10/8. 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.
Mon 12/149:37 am -
2 stops7h 57m
Wed 12/167:00 am -
1 stop9h 16m
Deal found 10/8![Delta logo]()
$867
This Booking.com deal was found by Cheapflights users on 10/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/44:36 pm -
3 stops30h 19m
Fri 11/67:00 am -
3 stops22h 13m
Deal found 10/7![Multiple Airlines logo]()
$817
This Air Canada deal was found by Cheapflights users on 10/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:29 am -
Nonstop2h 54m
Mon 11/28:15 am -
1 stop8h 29m
Deal found 10/10![Air Canada logo]()
$941
This Delta deal was found by Cheapflights users on 10/5. 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.
Wed 11/41:27 pm -
2 stops10h 52m
Wed 11/116:35 am -
1 stop5h 15m
Deal found 10/5![Delta logo]()
$891
This Air Canada deal was found by Cheapflights users on 10/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:35 am -
Nonstop2h 48m
Fri 11/62:15 pm -
Nonstop2h 35m
Deal found 10/7![Air Canada logo]()
$948
This Delta deal was found by Cheapflights users on 10/6. 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 10/226:30 am -
2 stops10h 20m
Thu 11/126:32 pm -
1 stop3h 01m
Deal found 10/6![Delta logo]()
$906
This Justfly.com deal was found by Cheapflights users on 10/10. 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 10/286:20 pm -
2 stops23h 50m
Mon 11/26:00 am -
2 stops28h 11m
Deal found 10/10![Multiple Airlines logo]()
$950
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 12/306:30 pm -
1 stop6h 14m
Mon 1/47:00 am -
1 stop9h 25m
Deal found 10/7![Delta logo]()
$1,054
Last-minute flights from Chicago to WinnipegDiscover last-minute flight deals from Chicago to Winnipeg. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Winnipeg. Data last updated October 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 10/225:30 pm -
1 stop7h 25m
Tue 10/279:35 pm -
2 stops15h 16m
Deal found 10/6![Multiple Airlines logo]()
$468
This Mytrip deal was found by Cheapflights users on 10/9. 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.
Wed 10/287:28 pm -
2 stops21h 57m
Thu 10/299:35 pm -
2 stops21h 10m
Deal found 10/9![Multiple Airlines logo]()
$453
This Mytrip deal was found by Cheapflights users on 10/9. 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.
Wed 10/286:42 pm -
2 stops22h 43m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 10/9![Multiple Airlines logo]()
$466
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Fri 10/306:42 pm -
2 stops22h 43m
Sun 11/19:35 pm -
2 stops20h 12m
Deal found 10/7![Multiple Airlines logo]()
$451
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Mon 11/26:42 pm -
2 stops22h 43m
Tue 11/179:35 pm -
2 stops20h 12m
Deal found 10/6![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Mon 11/212:15 pm -
1 stop22h 00m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/6![Multiple Airlines logo]()
$426
This Mytrip deal was found by Cheapflights users on 10/6. 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 11/37:35 pm -
2 stops21h 50m
Tue 11/109:35 pm -
2 stops20h 55m
Deal found 10/6![Multiple Airlines logo]()
$413
This Mytrip deal was found by Cheapflights users on 10/6. 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 11/36:16 am -
2 stops18h 54m
Tue 11/109:35 pm -
2 stops20h 12m
Deal found 10/6![Multiple Airlines logo]()
$449
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Mon 11/96:08 am -
2 stops19h 02m
Tue 11/179:35 pm -
2 stops20h 12m
Deal found 10/7![Multiple Airlines logo]()
$421
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Mon 11/97:50 pm -
2 stops29h 20m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/7![Multiple Airlines logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Tue 11/106:20 pm -
1 stop15h 55m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/5![Multiple Airlines logo]()
$419
This Mytrip deal was found by Cheapflights users on 10/5. 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 11/106:08 am -
2 stops29h 12m
Tue 11/179:35 pm -
2 stops20h 12m
Deal found 10/5![Multiple Airlines logo]()
$470
One-way flights from Chicago to WinnipegSearch for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
Search for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 2/26:00 am -
2 stops19h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Sat 1/306:00 am -
2 stops35h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Tue 10/277:15 am -
2 stops17h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Tue 11/177:35 pm -
2 stops21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Sat 1/301:18 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$192
This Trip.com deal was found by Cheapflights users on 10/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:16 am -
2 stops17h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 2/36:00 am -
2 stops19h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 2/21:18 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Sun 1/311:18 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 2/15:32 pm -
2 stops23h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 2/45:32 pm -
1 stop21h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/187:35 pm -
2 stops21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$205
Find flight deals from Chicago to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $354 (Kiwi.com) |
One-way from | $176 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $479 |
Good round-trip deal | $875 or less |
Good one-way deal | $337 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 October 10, 2026.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Mon 2/1
1:18 pm-6:25 pm
2 stops28h 07m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 11/19
6:08 am-2:10 am
2 stops19h 02m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 11/18
6:42 pm-2:10 am
2 stops30h 28m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/2
7:50 pm-2:10 am
2 stops29h 20m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$215
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/23
5:26 pm-6:25 pm
2 stops23h 59m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$242
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 11/17
12:27 pm-6:25 pm
3 stops28h 58m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$244
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 11/21
2:40 pm-3:20 pm
2 stops47h 40m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$245
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 10/26
8:04 am-1:10 am
3 stops41h 06m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 10/26
6:20 pm-6:10 pm
2 stops23h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 11/19
2:50 pm-10:52 pm
1 stop7h 02m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$321
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Chicago to Winnipeg
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
CHI-YWG
ORD-YWG
MDW-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 Chicago to Winnipeg
CHI-YWG
ORD-YWG
MDW-YWG
What is the cheapest month to book a flight from Chicago to Winnipeg?
Currently, September is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $512). Flying from Chicago to Winnipeg in January is currently the most expensive (average of $1,231). 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 CHI to YWG?
Find hourly flight availability from Chicago 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 October 10, 2026.
One of the essential ways to save on airfare from Chicago to Winnipeg 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 51% on airfare.
Weekly flight availability from Chicago to Winnipeg
Explore weekly flight availability from Chicago 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 October 10, 2026.
The most flights from CHI 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).
How much does it cost to fly round-trip from Chicago to Winnipeg?
Airfare is below average for this route at the moment.
Chicago to Winnipeg flights typically cost between $446 and $817 in January.The cheapest round-trip price found within the last 5 days was $354 on Multiple Airlines (Jan 13-Jan 15).
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 October 10, 2026.
Read reviews from past customers who have flown United Airlines and Air Canada from Chicago to Winnipeg. 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.
Food
6.7
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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Alternative routes for Chicago to Winnipeg
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Complete your trip
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Chicago and Winnipeg flights
Browse other Chicago and Winnipeg flight options. Last updated on October 10, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on October 10, 2026.
Popular flight searches
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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 October 10, 2026.
Top 3 airlines flying from Chicago to Winnipeg
Discover the top 3 airlines that operate flights from Chicago 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 7,457,451 searches. Data last updated October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$454 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$322 | Average$780 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |