- Regular
- StudentStudent Fare
Only students above 12 years of age are eligible for special fares and/or additional baggage allowances. Carrying valid student ID cards and student visas (where applicable) is mandatory, else the passenger may be denied boarding or asked to pay for extra baggage.
Popular Filters
One Way Price
Duration
Stops From Winnipeg
Departure From Winnipeg
₹ 28,471
₹ 24,592
₹ 24,592
Arrival at Chicago
₹ 28,621
₹ 31,299
₹ 24,592
₹ 24,592
Alliances & Airlines
Oneworld
()
SkyTeam
(5)
Star Alliance
(12)
Layover Airports
Layover Duration
Further Flights From Winnipeg (YWG)
Further Flights From Chicago (CHI)
Ahmedabad to Baku- 4 flights a week!
Limited Period Offers
Winnipeg Airport Contact Info
Address
Chicago Airport Contact Info
Address
Top International Routes
Top International Cities
Hotels in Winnipeg
Popular Hotels in Chicago
Hotels in Chicago
Premium Hotels Nearby Chicago
Winnipeg to Chicago Flight Schedule
Plan a trip like never before. Keep yourself informed with updated flight schedules for all airlines between Winnipeg - Chicago on Goibibo. Avail yourself with fit to pocket airfares for all major airlines. Also check Chicago Winnipeg Flight Schedule online.
₹ 27,582
₹ 2,990 Instant Discount
Special Deal Pre-applied for you
Winnipeg to Chicago , 6 Apr
Porter Airlines PD 424
06:00
Mon, 6 Apr 26
Winnipeg, Canada
02 h 32 m
09:32
Mon, 6 Apr 26
Terminal T3
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
Porter Airlines PD 6034 | Operated By American Airlines
11:40
Mon, 6 Apr 26
Terminal T3
Toronto, Canada
01 h 55 m
12:35
Mon, 6 Apr 26
Terminal T3
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Fare Option 1
Fare offered by airline.
₹ 27,582₹ 24,592
₹ 28,419
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
Air Canada AC 372
08:15
Mon, 6 Apr 26
Winnipeg, Canada
02 h 47 m
12:02
Mon, 6 Apr 26
Montreal, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 8481
13:20
Mon, 6 Apr 26
Montreal, Canada
02 h 35 m
14:55
Mon, 6 Apr 26
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic
Fare offered by airline.
₹ 28,419
Standard
Fare offered by airline.
₹ 6,640
₹ 30,855
Flex
Fare offered by airline.
₹ 36,084
Comfort
Fare offered by airline.
₹ 40,268
₹ 28,471
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
Air Canada AC 256
05:30
Mon, 6 Apr 26
Winnipeg, Canada
02 h 30 m
09:00
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 406
10:00
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
01 h 21 m
11:21
Mon, 6 Apr 26
Montreal, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 8481
13:20
Mon, 6 Apr 26
Montreal, Canada
02 h 35 m
14:55
Mon, 6 Apr 26
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Standard
Fare offered by airline.
₹ 13,280
₹ 28,471
Flex
Fare offered by airline.
₹ 36,834
Comfort
Fare offered by airline.
₹ 41,018
Latitude
Fare offered by airline.
₹ 80,745
₹ 28,621
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
Delta Air Lines DL 3871
11:55
Mon, 6 Apr 26
Winnipeg, Canada
01 h 34 m
13:29
Mon, 6 Apr 26
Terminal T1
Minneapolis, United States
BAGGAGE : CHECK INCABIN
Information not available
Delta Air Lines DL 1306
16:26
Mon, 6 Apr 26
Terminal T1
Minneapolis, United States
01 h 36 m
18:02
Mon, 6 Apr 26
Terminal T5
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Delta main basic
Fare offered by airline.
₹ 6,575
₹ 28,621
Delta main classic
Fare offered by airline.
₹ 31,057
Delta comfort classic
Fare offered by airline.
₹ 32,800
Delta comfort extra
Fare offered by airline.
₹ 37,683
₹ 28,621
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
United Airlines UA 5486
08:45
Mon, 6 Apr 26
Winnipeg, Canada
02 h 43 m
10:28
Mon, 6 Apr 26
Denver, United States
BAGGAGE : CHECK INCABIN
Information not available
United Airlines UA 2258
19:17
Mon, 6 Apr 26
Denver, United States
02 h 37 m
22:54
Mon, 6 Apr 26
Terminal T1
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic economy
Fare offered by airline.
₹ 9,895
₹ 28,621
Economy
Fare offered by airline.
₹ 31,057
Economy fully refundable
Fare offered by airline.
₹ 36,286
Economy plus
Fare offered by airline.
₹ 58,152
₹ 28,621
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
United Airlines UA 5486
08:45
Mon, 6 Apr 26
Winnipeg, Canada
02 h 43 m
10:28
Mon, 6 Apr 26
Denver, United States
BAGGAGE : CHECK INCABIN
Information not available
United Airlines UA 1488
20:52
Mon, 6 Apr 26
Denver, United States
02 h 37 m
00:29
Tue, 7 Apr 26
Terminal T1
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic economy
Fare offered by airline.
₹ 9,895
₹ 28,621
Economy
Fare offered by airline.
₹ 31,057
Economy fully refundable
Fare offered by airline.
₹ 36,286
Economy plus
Fare offered by airline.
₹ 61,371
₹ 31,299
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
Air Canada AC 256
05:30
Mon, 6 Apr 26
Winnipeg, Canada
02 h 30 m
09:00
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 3495 | Operated By United Airlines
10:15
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
02 h 03 m
11:18
Mon, 6 Apr 26
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Standard
Fare offered by airline.
₹ 6,640
₹ 31,299
Flex
Fare offered by airline.
₹ 36,528
Latitude
Fare offered by airline.
₹ 80,439
₹ 31,299
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
United Airlines UA 8444 | Operated By Air Canada
05:30
Mon, 6 Apr 26
Winnipeg, Canada
02 h 30 m
09:00
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
United Airlines UA 3473
10:15
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
02 h 03 m
11:18
Mon, 6 Apr 26
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Economy
Fare offered by airline.
₹ 31,299
Economy fully refundable
Fare offered by airline.
₹ 36,528
₹ 34,439
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
Air Canada AC 264
13:30
Mon, 6 Apr 26
Winnipeg, Canada
02 h 26 m
16:56
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 8913
18:30
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
01 h 55 m
19:25
Mon, 6 Apr 26
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic
Fare offered by airline.
₹ 34,439
Standard
Fare offered by airline.
₹ 6,640
₹ 36,880
Flex
Fare offered by airline.
₹ 42,104
Comfort
Fare offered by airline.
₹ 46,288
₹ 36,880
Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI
Winnipeg to Chicago , 6 Apr
United Airlines UA 8193 | Operated By Air Canada
13:30
Mon, 6 Apr 26
Winnipeg, Canada
02 h 26 m
16:56
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
United Airlines UA 8094 | Operated By Air Canada
18:30
Mon, 6 Apr 26
Terminal T1
Toronto, Canada
01 h 55 m
19:25
Mon, 6 Apr 26
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Economy
Fare offered by airline.
₹ 36,880
Economy fully refundable
Fare offered by airline.
₹ 42,104
Winnipeg to Chicago Flight Schedule
Planning to fly from Winnipeg to Chicago? Checking the latest Winnipeg to Chicago
flight schedule helps you plan your journey with ease. With multiple airlines offering frequent connections between
these two cities, passengers can choose flights that best suit their timing, budget, and comfort preferences.
Flights and Duration
Flights between and operate throughout the day, giving travelers
flexible options for departure and arrival. The average flight duration typically ranges between one to three hours
for most domestic routes, depending on the distance and weather conditions. Morning flights are ideal for business
travelers who need to reach Chicago early, while afternoon and evening flights cater to those who prefer
a more relaxed schedule.
Many airlines operate daily services on this route, ensuring a seamless and convenient travel experience.
You can find both non-stop and connecting flights based on your preferences.
Airlines Operating Between Winnipeg and Chicago
Leading airlines such as IndiGo, Air India, Vistara, SpiceJet, and Akasa Air offer regular flights between Winnipeg
and Chicago. Each carrier provides a unique flying experience — from premium cabin options to budget-friendly
fares. Depending on your travel needs, you can choose from early morning departures, mid-day flights, or late-night
schedules.
If you're looking for the most affordable option, the cheapest fare on this route currently starts at
₹27582 (subject to change). Prices may vary based on travel dates, seat availability, and booking time.
How to Check the Latest Flight Schedule
Flight timings and availability can change due to operational or weather factors. It's always best to verify the
Winnipeg to Chicago flight schedule before booking. Most online platforms display live schedules,
allowing you to compare airlines, departure times, and ticket prices in one place.
To get the best deals, try booking your flight at least a few weeks in advance. Early reservations often come with
lower fares and better seat options, especially during busy travel seasons or weekends.
- Arrive early: Reach at least two hours before departure to complete check-in and security formalities.
- Stay updated: Always recheck your flight status on the day of travel for any delays or gate changes.
- Compare options: Consider flight duration, layovers, and airline reputation when booking.
- Pack smart: Follow baggage allowance guidelines to avoid last-minute hassles.
| Winnipeg Chicago Cheap Flights | Fare | Date |
|---|---|---|
| Lowest Airfare Today | Rs 0 | |
| Cheapest Fare Within 30 Days | Rs 27582 |
06 Apr
|
| Cheapest Fare Within 90 Days | Rs 27582 |
06 Apr
|
| Cheapest Fare Within 365 Days | Rs 27582 |
06 Apr
|