Winnipeg International to Chicago flight ticket price
Compare live prices for YWG to ORD. Use the search panel
to change origin, destination, passengers, cabin and trip type instantly.
YWG → ORD10 May 2026Live inventory
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Showing 25
of 168
live flights
westjet
WS-223
07:00
05/10/2026
YWG
Winnipeg International Airport
9h 40m
1 Stop
⏱ YYC · 3h 45mYYC Airport
16:40
05/10/2026
ORD
Chicago Airport
₹18,798
per person
✕ Non-refundable7 fare options
Delta Air Lines
DL-3871
11:55
05/10/2026
YWG
Winnipeg International Airport
4h 56m
1 Stop
⏱ MSP · 1h 47mMSP Airport
16:51
05/10/2026
ORD
Chicago Airport
₹19,692
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-3660
06:40
05/10/2026
YWG
Winnipeg International Airport
6h 39m
1 Stop
⏱ MSP · 3h 29mMSP Airport
13:19
05/10/2026
MDW
Chicago Airport
₹19,692
per person
✕ Non-refundable
Delta Airlines
DL-3871
11:55
05/10/2026
YWG
Winnipeg International Airport
7h 25m
1 Stop
⏱ MSP · 4h 10mMSP Airport
19:20
05/10/2026
ORD
Chicago Airport
₹19,792
per person
✕ Non-refundable5 fare options
aircanada
AC-258
08:10
05/10/2026
YWG
Winnipeg International Airport
6h 45m
1 Stop
⏱ YYZ · 2h 15mYYZ Airport
14:55
05/10/2026
ORD
Chicago Airport
₹19,933
per person
✕ Non-refundable18 fare options
aircanada
AC-256
05:10
05/10/2026
YWG
Winnipeg International Airport
8h 15m
1 Stop
⏱ YYZ · 3h 45mYYZ Airport
13:25
05/10/2026
ORD
Chicago Airport
₹19,933
per person
✕ Non-refundable18 fare options
Delta Air Lines
DL-3660
06:40
05/10/2026
YWG
Winnipeg International Airport
8h 17m
1 Stop
⏱ MSP · 5h 9mMSP Airport
14:57
05/10/2026
ORD
Chicago Airport
₹20,443
per person
✕ Non-refundable
aircanada
AC-3920
14:00
05/10/2026
YWG
Winnipeg International Airport
2h 35m
Non-stop
16:35
05/10/2026
ORD
Chicago Airport
₹20,941
per person
✕ Non-refundable23 fare options
WestJet
WS-221
06:00
05/10/2026
YWG
Winnipeg International Airport
10h 40m
1 Stop
⏱ YYC · 4h 45mYYC Airport
16:40
05/10/2026
ORD
Chicago Airport
₹21,846
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-4005
17:41
05/10/2026
YWG
Winnipeg International Airport
3h 39m
1 Stop
⏱ MSP · 0h 30mMSP Airport
21:20
05/10/2026
ORD
Chicago Airport
₹22,186
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-3660
06:40
05/10/2026
YWG
Winnipeg International Airport
5h 7m
1 Stop
⏱ MSP · 1h 59mMSP Airport
11:47
05/10/2026
ORD
Chicago Airport
₹22,186
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-3871
11:55
05/10/2026
YWG
Winnipeg International Airport
6h 1m
1 Stop
⏱ MSP · 2h 52mMSP Airport
17:56
05/10/2026
MDW
Chicago Airport
₹22,186
per person
✕ Non-refundable
Delta Airlines
DL-3526
15:50
05/10/2026
YWG
Winnipeg International Airport
5h 30m
1 Stop
⏱ MSP · 2h 24mMSP Airport
21:20
05/10/2026
ORD
Chicago Airport
₹22,286
per person
✕ Non-refundable5 fare options
aircanada
AC-258
08:10
05/10/2026
YWG
Winnipeg International Airport
5h 51m
1 Stop
⏱ YYZ · 1h 20mYYZ Airport
14:01
05/10/2026
ORD
Chicago Airport
₹22,427
per person
✕ Non-refundable16 fare options
Air Canada
AC-256
05:10
05/10/2026
YWG
Winnipeg International Airport
6h 8m
1 Stop
⏱ YYZ · 1h 35mYYZ Airport
11:18
05/10/2026
ORD
Chicago Airport
₹22,437
per person
✕ Non-refundable🔥 Last 1 seats15 fare options
Air Canada
AC-256
05:10
05/10/2026
YWG
Winnipeg International Airport
6h 53m
1 Stop
⏱ YYZ · 2h 20mYYZ Airport
12:03
05/10/2026
ORD
Chicago Airport
₹22,437
per person
✕ Non-refundable🔥 Last 1 seats15 fare options
Porter Airlines
PD-422
09:20
05/10/2026
YWG
Winnipeg International Airport
6h 58m
1 Stop
⏱ YYZ · 2h 28mYYZ Airport
16:18
05/10/2026
ORD
Chicago Airport
₹22,631
per person
✕ Non-refundable2 fare options
Air Canada
AC-3711
08:45
05/10/2026
YWG
Winnipeg International Airport
14h 13m
1 Stop
⏱ DEN · 8h 52mDEN Airport
22:58
05/10/2026
ORD
Chicago Airport
₹22,967
per person
✕ Non-refundable
Air Canada
AC-3711
08:45
05/10/2026
YWG
Winnipeg International Airport
15h 12m
1 Stop
⏱ DEN · 9h 52mDEN Airport
23:57
05/10/2026
ORD
Chicago Airport
₹22,967
per person
✕ Non-refundable
Air Canada
AC-3711
08:45
05/10/2026
YWG
Winnipeg International Airport
16h 13m
1 Stop
⏱ DEN · 10h 52mDEN Airport
00:58
05/11/2026
+1
ORD
Chicago Airport
₹22,967
per person
✕ Non-refundable
Air Canada
AC-256
05:10
05/10/2026
YWG
Winnipeg International Airport
9h 45m
1 Stop
⏱ YYZ · 5h 15mYYZ Airport
14:55
05/10/2026
ORD
Chicago Airport
₹23,014
per person
✕ Non-refundable
Air Canada
AC-256
05:10
05/10/2026
YWG
Winnipeg International Airport
14h 30m
1 Stop
⏱ YYZ · 10h 0mYYZ Airport
19:40
05/10/2026
ORD
Chicago Airport
₹23,014
per person
✕ Non-refundable
Air Canada
AC-258
08:10
05/10/2026
YWG
Winnipeg International Airport
11h 30m
1 Stop
⏱ YYZ · 7h 0mYYZ Airport
19:40
05/10/2026
ORD
Chicago Airport
₹23,014
per person
✕ Non-refundable🔥 Last 2 seats
Air Canada
AC-270
19:20
05/10/2026
YWG
Winnipeg International Airport
12h 40m
1 Stop
⏱ YYZ · 8h 16mYYZ Airport
08:00
05/11/2026
+1
ORD
Chicago Airport
₹24,738
per person
✕ Non-refundable🔥 Last 1 seats16 fare options
Air Canada
AC-256
05:10
05/10/2026
YWG
Winnipeg International Airport
8h 51m
1 Stop
⏱ YYZ · 4h 20mYYZ Airport
14:01
05/10/2026
ORD
Chicago Airport
₹24,740
per person
✕ Non-refundable3 fare options
😕 No flights match your filters.
Winnipeg International (YWG)
Chicago (ORD)
📅 Results on this page are loaded for 10 May 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
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❓ 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.