Winnipeg International (YWG) to Chicago (ORD) Flights from ₹27,666
Fares on this route currently start from ₹27,666. Compare live YWG to ORD prices, non-stop and connecting flights, departure times and airline choices before booking. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
YWG → ORD04 Jun 2026Live inventory
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Showing 25
of 114
live flights
American Airlines
AA-9107
20:45
06/04/2026
YWG
Winnipeg International Airport
11h 50m
1 Stop
⏱ YYZ · 7h 15mYYZ Airport
08:35
06/05/2026
+1
ORD
Chicago Airport
₹27,666
per person
✕ Non-refundable9 fare options
American Airlines
AA-9107
20:45
06/04/2026
YWG
Winnipeg International Airport
17h 35m
1 Stop
⏱ YYZ · 13h 5mYYZ Airport
14:20
06/05/2026
+1
ORD
Chicago Airport
₹27,818
per person
✕ Non-refundable3 fare options
American Airlines
AA-9107
20:45
06/04/2026
YWG
Winnipeg International Airport
15h 59m
1 Stop
⏱ YYZ · 11h 29mYYZ Airport
12:44
06/05/2026
+1
ORD
Chicago Airport
₹32,779
per person
✕ Non-refundable2 fare options
American Airlines
AA-9107
20:45
06/04/2026
YWG
Winnipeg International Airport
19h 33m
1 Stop
⏱ YYZ · 15h 3mYYZ Airport
16:18
06/05/2026
+1
ORD
Chicago Airport
₹32,779
per person
✕ Non-refundable2 fare options
United Airlines
UA-5747
07:00
06/04/2026
YWG
Winnipeg International Airport
2h 34m
Non-stop
09:34
06/04/2026
ORD
Chicago Airport
₹36,513
per person
✕ Non-refundable10 fare options
United Airlines
UA-5250
12:56
06/04/2026
YWG
Winnipeg International Airport
2h 34m
Non-stop
15:30
06/04/2026
ORD
Chicago Airport
₹36,513
per person
✕ Non-refundable9 fare options
United Airlines
UA-5486
08:45
06/04/2026
YWG
Winnipeg International Airport
10h 6m
1 Stop
⏱ DEN · 4h 40mDEN Airport
18:51
06/04/2026
ORD
Chicago Airport
₹37,241
per person
✕ Non-refundable🔥 Last 5 seats3 fare options
aircanada
AC-258
08:10
06/04/2026
YWG
Winnipeg International Airport
6h 45m
1 Stop
⏱ YYZ · 2h 15mYYZ Airport
14:55
06/04/2026
ORD
Chicago Airport
₹37,294
per person
✕ Non-refundable12 fare options
aircanada
AC-256
05:10
06/04/2026
YWG
Winnipeg International Airport
8h 15m
1 Stop
⏱ YYZ · 3h 45mYYZ Airport
13:25
06/04/2026
ORD
Chicago Airport
₹37,294
per person
✕ Non-refundable12 fare options
Delta Air Lines
DL-3660
06:40
06/04/2026
YWG
Winnipeg International Airport
8h 17m
1 Stop
⏱ MSP · 5h 9mMSP Airport
14:57
06/04/2026
ORD
Chicago Airport
₹37,412
per person
✕ Non-refundable
aircanada
AC-8331
07:20
06/04/2026
YWG
Winnipeg International Airport
9h 45m
1 Stop
⏱ YYC · 4h 0mYYC Airport
17:05
06/04/2026
ORD
Chicago Airport
₹38,456
per person
✓ Refundable14 fare options
aircanada
AC-4135
07:00
06/04/2026
YWG
Winnipeg International Airport
2h 34m
Non-stop
09:34
06/04/2026
ORD
Chicago Airport
₹39,054
per person
✕ Non-refundable12 fare options
aircanada
AC-3760
12:56
06/04/2026
YWG
Winnipeg International Airport
2h 34m
Non-stop
15:30
06/04/2026
ORD
Chicago Airport
₹39,054
per person
✕ Non-refundable12 fare options
aircanada
AC-258
08:10
06/04/2026
YWG
Winnipeg International Airport
12h 6m
1 Stop
⏱ YYZ · 7h 40mYYZ Airport
20:16
06/04/2026
ORD
Chicago Airport
₹39,166
per person
✕ Non-refundable
aircanada
AC-256
05:10
06/04/2026
YWG
Winnipeg International Airport
15h 6m
1 Stop
⏱ YYZ · 10h 40mYYZ Airport
20:16
06/04/2026
ORD
Chicago Airport
₹39,166
per person
✕ Non-refundable
aircanada
AC-3711
08:45
06/04/2026
YWG
Winnipeg International Airport
10h 6m
1 Stop
⏱ DEN · 4h 40mDEN Airport
18:51
06/04/2026
ORD
Chicago Airport
₹39,795
per person
✓ Refundable8 fare options
aircanada
AC-256
05:10
06/04/2026
YWG
Winnipeg International Airport
6h 50m
1 Stop
⏱ YYZ · 2h 20mYYZ Airport
12:00
06/04/2026
ORD
Chicago Airport
₹39,835
per person
✕ Non-refundable13 fare options
United Airlines
UA-8444
05:10
06/04/2026
YWG
Winnipeg International Airport
6h 11m
1 Stop
⏱ YYZ · 1h 35mYYZ Airport
11:21
06/04/2026
ORD
Chicago Airport
₹39,835
per person
✕ Non-refundable5 fare options
United Airlines
UA-8444
05:10
06/04/2026
YWG
Winnipeg International Airport
6h 50m
1 Stop
⏱ YYZ · 2h 20mYYZ Airport
12:00
06/04/2026
ORD
Chicago Airport
₹39,835
per person
✕ Non-refundable5 fare options
United Airlines
UA-8220
15:15
06/04/2026
YWG
Winnipeg International Airport
6h 50m
1 Stop
⏱ YYZ · 2h 15mYYZ Airport
22:05
06/04/2026
ORD
Chicago Airport
₹39,835
per person
✕ Non-refundable5 fare options
aircanada
AC-258
08:10
06/04/2026
YWG
Winnipeg International Airport
8h 49m
1 Stop
⏱ YYZ · 4h 20mYYZ Airport
16:59
06/04/2026
ORD
Chicago Airport
₹39,848
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-4005
17:41
06/04/2026
YWG
Winnipeg International Airport
3h 39m
1 Stop
⏱ MSP · 0h 30mMSP Airport
21:20
06/04/2026
ORD
Chicago Airport
₹39,946
per person
✕ Non-refundable6 fare options
aircanada
AC-3711
08:45
06/04/2026
YWG
Winnipeg International Airport
11h 26m
1 Stop
⏱ DEN · 6h 3mDEN Airport
20:11
06/04/2026
ORD
Chicago Airport
₹39,979
per person
✕ Non-refundable🔥 Last 5 seats
aircanada
AC-3711
08:45
06/04/2026
YWG
Winnipeg International Airport
11h 45m
1 Stop
⏱ DEN · 6h 19mDEN Airport
20:30
06/04/2026
ORD
Chicago Airport
₹39,979
per person
✕ Non-refundable🔥 Last 5 seats
aircanada
AC-3711
08:45
06/04/2026
YWG
Winnipeg International Airport
13h 9m
1 Stop
⏱ DEN · 7h 49mDEN Airport
21:54
06/04/2026
ORD
Chicago Airport
₹39,979
per person
✕ Non-refundable🔥 Last 5 seats
😕 No flights match your filters.
Winnipeg International (YWG)
Chicago (ORD)
📅 Results on this page are loaded for 04 Jun 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.
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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.