Compare live prices for YWG to ORD on
Tue, 14 Apr 2026. Use the search panel
to change origin, destination, passengers, cabin and trip type instantly.
YWG → ORD14 Apr 2026Live inventory
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Showing 25
of 138
live flights
WestJet
WS-6853
17:20
04/14/2026
YWG
24h 53m
1 Stop
⏱ MSP · 21h 39m
18:13
04/15/2026
+1
ORD
₹26,914
per person
✕ Non-refundable5 fare options
WestJet
WS-6853
17:20
04/14/2026
YWG
4h 18m
1 Stop
⏱ MSP · 1h 3m
21:38
04/14/2026
ORD
₹26,914
per person
✕ Non-refundable5 fare options
WestJet
WS-483
06:45
04/14/2026
YWG
11h 28m
2 Stops
⏱ YEG · 1h 13m⏱ MSP · 3h 30m
18:13
04/14/2026
ORD
₹27,079
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-4005
17:20
04/14/2026
YWG
14h 36m
2 Stops
⏱ MSP · 1h 9m⏱ LGA · 6h 24m
07:56
04/15/2026
+1
ORD
₹27,169
per person
✕ Non-refundable
WestJet
WS-6853
17:20
04/14/2026
YWG
26h 32m
1 Stop
⏱ MSP · 23h 18m
19:52
04/15/2026
+1
ORD
₹27,419
per person
✕ Non-refundable🔥 Last 1 seats
WestJet
WS-6853
17:20
04/14/2026
YWG
25h 16m
1 Stop
⏱ MSP · 22h 0m
18:36
04/15/2026
+1
MDW
₹27,419
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
11h 47m
2 Stops
⏱ YYZ · 1h 26m⏱ LGA · 3h 13m
16:47
04/14/2026
ORD
₹27,848
per person
✕ Non-refundable5 fare options
WestJet
WS-382
05:00
04/14/2026
YWG
13h 13m
2 Stops
⏱ YYZ · 3h 48m⏱ MSP · 2h 47m
18:13
04/14/2026
ORD
₹27,848
per person
✕ Non-refundable5 fare options
WestJet
WS-382
05:00
04/14/2026
YWG
15h 40m
2 Stops
⏱ YYZ · 3h 42m⏱ DTW · 6h 31m
20:40
04/14/2026
ORD
₹28,010
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
13h 52m
2 Stops
⏱ YYZ · 3h 42m⏱ DTW · 4h 36m
18:52
04/14/2026
ORD
₹28,010
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
12h 58m
2 Stops
⏱ YYZ · 3h 42m⏱ DTW · 4h 1m
17:58
04/14/2026
MDW
₹28,010
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
13h 35m
2 Stops
⏱ YYZ · 2h 56m⏱ ATL · 3h 39m
18:35
04/14/2026
ORD
₹28,010
per person
✕ Non-refundable3 fare options
Delta Air Lines
DL-3871
11:55
04/14/2026
YWG
25h 28m
2 Stops
⏱ MSP · 5h 20m⏱ SEA · 10h 33m
13:23
04/15/2026
+1
ORD
₹28,690
per person
✕ Non-refundable2 fare options
Delta Air Lines
DL-3871
11:55
04/14/2026
YWG
28h 44m
2 Stops
⏱ MSP · 5h 20m⏱ SEA · 13h 53m
16:39
04/15/2026
+1
ORD
₹28,690
per person
✕ Non-refundable
Delta Air Lines
DL-3871
11:55
04/14/2026
YWG
36h 3m
2 Stops
⏱ MSP · 5h 20m⏱ SEA · 21h 17m
23:58
04/15/2026
+1
ORD
₹28,690
per person
✕ Non-refundable
WestJet
WS-229
07:50
04/14/2026
YWG
13h 28m
2 Stops
⏱ YYC · 3h 18m⏱ SLC · 2h 24m
21:18
04/14/2026
ORD
₹29,337
per person
✕ Non-refundable🔥 Last 5 seats5 fare options
WestJet
WS-539
05:55
04/14/2026
YWG
15h 43m
2 Stops
⏱ YVR · 4h 52m⏱ MSP · 2h 29m
21:38
04/14/2026
ORD
₹29,865
per person
✕ Non-refundable🔥 Last 4 seats5 fare options
WestJet
WS-539
05:55
04/14/2026
YWG
13h 57m
2 Stops
⏱ YVR · 4h 52m⏱ MSP · 0h 44m
19:52
04/14/2026
ORD
₹29,865
per person
✕ Non-refundable🔥 Last 4 seats5 fare options
WestJet
WS-382
05:00
04/14/2026
YWG
11h 18m
2 Stops
⏱ YYZ · 3h 42m⏱ DTW · 2h 11m
16:18
04/14/2026
ORD
₹30,109
per person
✕ Non-refundable5 fare options
WestJet
WS-386
20:05
04/14/2026
YWG
22h 30m
2 Stops
⏱ YYZ · 11h 55m⏱ ATL · 3h 39m
18:35
04/15/2026
+1
ORD
₹30,358
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
15h 40m
2 Stops
⏱ YYZ · 5h 41m⏱ DTW · 4h 31m
20:40
04/14/2026
ORD
₹30,358
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
15h 40m
2 Stops
⏱ YYZ · 7h 37m⏱ DTW · 2h 35m
20:40
04/14/2026
ORD
₹30,358
per person
✕ Non-refundable
WestJet
WS-386
20:05
04/14/2026
YWG
22h 30m
2 Stops
⏱ YYZ · 13h 55m⏱ ATL · 1h 42m
18:35
04/15/2026
+1
ORD
₹30,358
per person
✕ Non-refundable🔥 Last 4 seats
WestJet
WS-382
05:00
04/14/2026
YWG
13h 52m
2 Stops
⏱ YYZ · 7h 37m⏱ DTW · 0h 40m
18:52
04/14/2026
ORD
₹30,358
per person
✕ Non-refundable
WestJet
WS-382
05:00
04/14/2026
YWG
12h 58m
2 Stops
⏱ YYZ · 5h 41m⏱ DTW · 2h 1m
17:58
04/14/2026
MDW
₹30,358
per person
✕ Non-refundable
😕 No flights match your filters.
Winnipeg International (YWG)
Chicago (ORD)
📅 Results on this page are loaded for 14 Apr 2026. Click View all flights for the complete live search.
Winnipeg International to Chicago — what to expect when booking
The YWG–ORD route is served by multiple carriers throughout the year.
Fares on this route can move quickly — a price available now may not be there 30 minutes later.
If your dates are flexible, try shifting your departure by a day or two using the date strip above.
Mid-week departures often show lower base fares compared to weekend starts on many routes.
Before you book
Compare nearby dates
The date strip above lets you scan nearby fares without restarting the search.
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Each result shows baggage, refundability and fare details before you proceed.
❓ Frequently asked questions — Winnipeg International to Chicago flights
Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.
The straight-line distance between Winnipeg International,Canada (YWG) and Chicago,USA (ORD) is approximately shown in the route details above. Actual flying distance may vary slightly depending on routing.
Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.