$212+ Cheap flights from Chicago (CHI) to Manitoba
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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Nov 26 — Dec 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Manitoba 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 Manitoba
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Cheapest flights from Chicago to ManitobaExplore the most affordable flight options available from Chicago to Manitoba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2026.
Explore the most affordable flight options available from Chicago to Manitoba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 12/36:20 pm -
1 stop14h 55m
Sun 12/67:55 pm -
1 stop16h 40m
Deal found 10/24![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/106:20 pm -
1 stop14h 55m
Sun 12/139:35 pm -
2 stops25h 07m
Deal found 10/22![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/13:55 pm -
2 stops32h 15m
Wed 12/94:00 pm -
1 stop19h 32m
Deal found 10/23![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/215:58 am -
1 stop7h 42m
Thu 1/289:35 pm -
2 stops15h 15m
Deal found 10/26![Multiple Airlines logo]()
$464
This Mytrip deal was found by Cheapflights users on 10/22. 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.
Sat 11/216:20 pm -
1 stop14h 55m
Mon 11/237:55 pm -
1 stop14h 28m
Deal found 10/22![Multiple Airlines logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/13:55 pm -
2 stops32h 15m
Tue 12/88:00 am -
1 stop18h 08m
Deal found 10/25![Multiple Airlines logo]()
$502
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Fri 12/181:11 pm -
2 stops27h 14m
Mon 12/287:00 am -
1 stop18h 01m
Deal found 10/25![Multiple Airlines logo]()
$593
This Booking.com deal was found by Cheapflights users on 10/27. 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 11/1112:27 pm -
3 stops27h 58m
Thu 11/199:35 pm -
2 stops15h 20m
Deal found 10/27![Multiple Airlines logo]()
$620
This Mytrip deal was found by Cheapflights users on 10/23. 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.
Thu 12/105:02 pm -
2 stops23h 23m
Sun 12/137:55 pm -
2 stops14h 42m
Deal found 10/23![Multiple Airlines logo]()
$699
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/112:33 pm -
2 stops27h 52m
Tue 12/85:45 pm -
1 stop24h 05m
Deal found 10/27![Multiple Airlines logo]()
$717
This Mytrip deal was found by Cheapflights users on 10/22. 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.
Sun 12/68:37 pm -
3 stops27h 33m
Sun 12/139:35 pm -
2 stops19h 31m
Deal found 10/22![Multiple Airlines logo]()
$744
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/112:33 pm -
2 stops27h 52m
Wed 12/95:24 pm -
1 stop24h 26m
Deal found 10/23![Multiple Airlines logo]()
$752
Best flights from Chicago to ManitobaDiscover carefully curated flight deals from Chicago to Manitoba that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
Discover carefully curated flight deals from Chicago to Manitoba that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Fri 2/56:00 am -
1 stop7h 40m
Sun 2/712:40 pm -
2 stops23h 50m
Deal found 10/26![Multiple Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/192:50 pm -
1 stop7h 02m
Thu 11/267:00 am -
1 stop7h 10m
Deal found 10/22![American Airlines logo]()
$639
This FlightHub deal was found by Cheapflights users on 10/26. 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.
Fri 4/29:41 am -
1 stop25h 01m
Tue 4/67:00 am -
1 stop7h 20m
Deal found 10/26![Porter Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 10/24. 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 11/2410:34 am -
1 stop12h 59m
Thu 12/36:25 am -
1 stop11h 25m
Deal found 10/24![Delta logo]()
$779
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/110:24 am -
1 stop13h 15m
Tue 12/85:45 pm -
1 stop24h 05m
Deal found 10/27![WestJet logo]()
$994
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/2112:15 pm -
1 stop9h 37m
Mon 11/239:35 pm -
2 stops15h 00m
Deal found 10/22![Multiple Airlines logo]()
$504
This Booking.com deal was found by Cheapflights users on 10/22. 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.
Thu 12/107:20 am -
2 stops10h 54m
Sun 12/139:35 pm -
2 stops15h 00m
Deal found 10/22![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 3/66:20 pm -
1 stop14h 55m
Sat 3/136:00 am -
1 stop12h 30m
Deal found 10/26![Multiple Airlines logo]()
$614
This Porter Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 3/112:52 pm -
1 stop7h 05m
Fri 3/198:00 am -
1 stop6h 37m
Deal found 10/22![Porter Airlines logo]()
$761
This Booking.com deal was found by Cheapflights users on 10/27. 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 11/1112:27 pm -
3 stops27h 58m
Thu 11/199:35 pm -
3 stops23h 12m
Deal found 10/27![Multiple Airlines logo]()
$690
This Delta deal was found by Cheapflights users on 10/23. 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 12/11:41 pm -
2 stops9h 58m
Wed 12/96:25 am -
2 stops12h 36m
Deal found 10/23![Delta logo]()
$952
This Delta deal was found by Cheapflights users on 10/24. 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 11/251:31 pm -
2 stops10h 02m
Tue 12/112:22 pm -
1 stop5h 28m
Deal found 10/24![Delta logo]()
$965
This Mytrip deal was found by Cheapflights users on 10/22. 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.
Sun 12/68:37 pm -
3 stops27h 33m
Sun 12/139:35 pm -
2 stops19h 31m
Deal found 10/22![Multiple Airlines logo]()
$744
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/108:37 pm -
2 stops23h 13m
Sun 12/136:25 am -
1 stop6h 34m
Deal found 10/23![Multiple Airlines logo]()
$762
This Mytrip deal was found by Cheapflights users on 10/27. 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 12/15:30 pm -
2 stops15h 45m
Tue 12/84:45 pm -
2 stops19h 48m
Deal found 10/27![Multiple Airlines logo]()
$771
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/108:37 pm -
1 stop27h 07m
Thu 12/177:00 am -
2 stops10h 16m
Deal found 10/25![Multiple Airlines logo]()
$909
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/712:20 pm -
2 stops25h 10m
Tue 11/1012:44 pm -
1 stop24h 06m
Deal found 10/24![Multiple Airlines logo]()
$993
Last-minute flights from Chicago to ManitobaDiscover last-minute flight deals from Chicago to Manitoba. Data last updated October 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Manitoba. Data last updated October 27, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 10/27. 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 11/1112:27 pm -
3 stops27h 58m
Thu 11/199:35 pm -
2 stops15h 20m
Deal found 10/27![Multiple Airlines logo]()
$620
This Mytrip deal was found by Cheapflights users on 10/22. 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.
Thu 11/197:31 am -
2 stops16h 39m
Thu 11/268:35 am -
3 stops17h 18m
Deal found 10/22![Multiple Airlines logo]()
$574
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/192:50 pm -
1 stop7h 02m
Thu 11/267:00 am -
1 stop7h 10m
Deal found 10/22![American Airlines logo]()
$639
This Mytrip deal was found by Cheapflights users on 10/22. 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.
Sat 11/216:20 pm -
1 stop14h 55m
Mon 11/237:55 pm -
1 stop14h 28m
Deal found 10/22![Multiple Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 10/24. 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 11/2110:34 am -
1 stop12h 59m
Thu 12/36:25 am -
1 stop11h 25m
Deal found 10/24![Delta logo]()
$826
This FlightHub deal was found by Cheapflights users on 10/24. 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.
Mon 11/236:20 pm -
2 stops23h 46m
Tue 12/17:00 am -
1 stop7h 10m
Deal found 10/24![Porter Airlines logo]()
$604
This Mytrip deal was found by Cheapflights users on 10/22. 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 11/245:26 pm -
2 stops22h 59m
Tue 12/19:35 pm -
2 stops17h 17m
Deal found 10/22![Multiple Airlines logo]()
$519
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Tue 11/242:50 pm -
1 stop7h 02m
Tue 12/17:00 am -
1 stop7h 10m
Deal found 10/22![American Airlines logo]()
$571
This FlightHub deal was found by Cheapflights users on 10/24. 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.
Tue 11/242:50 pm -
1 stop7h 02m
Tue 12/17:00 am -
1 stop7h 10m
Deal found 10/24![Porter Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 10/24. 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 11/2410:34 am -
1 stop12h 59m
Thu 12/36:25 am -
1 stop11h 25m
Deal found 10/24![Delta logo]()
$779
This Delta deal was found by Cheapflights users on 10/24. 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 11/2410:34 am -
1 stop12h 59m
Wed 12/26:25 am -
1 stop11h 25m
Deal found 10/24![Delta logo]()
$804
This FlightHub deal was found by Cheapflights users on 10/24. 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.
Wed 11/252:50 pm -
1 stop7h 02m
Tue 12/17:00 am -
1 stop7h 10m
Deal found 10/24![Porter Airlines logo]()
$637
One-way flights from Chicago to ManitobaSearch for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
Search for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/78:15 am -
2 stops32h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 12/46:20 pm -
2 stops23h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Porter Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 12/43:36 pm -
3 stops26h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/235:26 pm -
2 stops30h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/105:02 pm -
2 stops23h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/108:15 am -
2 stops15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/75:02 pm -
2 stops23h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/116:20 pm -
1 stop14h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 12/72:50 pm -
1 stop7h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 12/43:55 pm -
3 stops32h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/222:52 pm -
3 stops33h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/221:16 pm -
2 stops30h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$343
Find flight deals from Chicago to Manitoba
Keep the following information in mind while searching for Chicago to Manitoba flight deals. Data was last updated October 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $376 (Kiwi.com) |
One-way from | $212 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $817 |
Good round-trip deal | $472 or less |
Good one-way deal | $394 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Manitoba 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 27, 2026.
Use the filters below to find and compare flights from Chicago to Manitoba that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 12/4
3:36 pm-7:14 pm
3 stops26h 38m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$233
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Mon 12/7
5:02 pm-5:25 pm
2 stops23h 23m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$239
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 12/7
4:08 pm-5:25 pm
3 stops24h 17m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 12/7
2:50 pm-10:57 pm
1 stop7h 07m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 12/4
3:55 pm-1:10 am
3 stops32h 15m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$260
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 11/11
7:35 pm-5:25 pm
2 stops20h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$271
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 12/10
5:02 pm-8:50 pm
3 stops26h 48m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$285
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 12/10
4:08 pm-5:25 pm
3 stops24h 17m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$294
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/23
2:50 pm-10:52 pm
1 stop7h 02m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$321
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 12/10
2:50 pm-10:57 pm
1 stop7h 07m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$321
Showing 1-10 of 36 resultsSorted by cheapest first
Best time to book a flight from Chicago to Manitoba
Have a flexible travel schedule? Discover the best time to fly to Manitoba from Chicago with our price prediction graph.
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 Manitoba
CHI-CAMB
ORD-YWG
MDW-YWG
What is the cheapest month to book a flight from Chicago to Manitoba?
Currently, September is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $512). Flying from Chicago to Manitoba 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 MB?
Find hourly flight availability from Chicago to Manitoba. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2026.
It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight at noon.
Reviews of airlines servicing Manitoba
Get insights into the airlines that provide service to Manitoba. 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 Manitoba. Reviews last updated October 27, 2026.
Get a feel of what it's like to fly with United Airlines and Air Canada from Chicago to Manitoba by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
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 Manitoba. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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.
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Alternative routes for Chicago to Manitoba
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Manitoba by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Manitoba by cabin class
Find flights from Chicago to Manitoba, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Manitoba flights
Browse other Chicago and Manitoba flight options. Last updated on October 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Manitoba
Discover the top 3 airlines that operate flights from Chicago to Manitoba. 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$208 | Average$454 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$291 | Average$762 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$322 | Average$780 | FlexibilityNo cancel fee | On-time67% |