December is by far the best month, wherein you can get cheapest flights for Winnipeg to Chicago American Airlines. Meanwhile, November is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.
One Way Fare December- During this month the footfall is less so, the flight is gradually inexpensive.
Round Trip Fare December - is the cheapest month to book round trip flights.
Cheapest Fare- Currently, this is the fare price based on the current demand.
Disclaimer - All the mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.
YWG
06:00
Winnipeg Winnipeg James Armstrong Richardson International Airport
Mon , 08 Dec 2025
ORD
12:31
Chicago Chicago O Hare International Airport
Mon, 08 Dec 2025
YWG
12:10
Winnipeg Winnipeg James Armstrong Richardson International Airport
Mon , 08 Dec 2025
ORD
19:24
Chicago Chicago O Hare International Airport
Mon, 08 Dec 2025
YWG
06:00
Winnipeg Winnipeg James Armstrong Richardson International Airport
Thu , 13 Nov 2025
ORD
14:14
Chicago Chicago O Hare International Airport
Thu, 13 Nov 2025
YWG
06:00
Winnipeg Winnipeg James Armstrong Richardson International Airport
Mon , 10 Nov 2025
ORD
12:27
Chicago Chicago O Hare International Airport
Mon, 10 Nov 2025
YWG
12:10
Winnipeg Winnipeg James Armstrong Richardson International Airport
Mon , 01 Dec 2025
ORD
19:20
Chicago Chicago O Hare International Airport
Mon, 01 Dec 2025
To crack the better offer on Winnipeg to Chicago American Airlines , it’s better to make advanced bookings at least few weeks prior of your intended date because price might rise eventually due to the delay.
Weekdays are the best day to get low-cost flight tickets from Winnipeg to Chicago American Airlines. However, it depends on a certain factor. If the demand is high and festivals are there, then prices could be a little high.
You can book your American Airlines to travel from Winnipeg (YWG) to Chicago (ORD) with ease and convenience at the starting fare of ₹ 23422 via EaseMyTrip. Usually, the price of an American Airlines ticket from Winnipeg to Chicago varies from ₹ 23422 to ₹ 30555. This is due to the fluctuating demand during peak seasons and festive seasons. However, with EaseMyTrip, you can avail exclusive discounts and offers to book a flight ticket within your budget.
In addition to this, when you book your flight ticket via EaseMyTrip, we equip you with comprehensive information like airline number, schedule, departure status and arrival time, thereby making your journey hassle-free. You can always rely on us for exciting deals and offers for booking your American Airlines ticket from Winnipeg to Chicago.
Constantly browsing the internet for cheap Winnipeg to Chicago American Airlines can be a tedious task. However, you can simplify it with the help of EaseMyTrip. Our database can help you with relevant flight information and with exclusive discounts and deals, you can book your American Airlines Winnipeg to Chicago in a budget friendly manner.
The aerial distance between Winnipeg and Chicago is 1148 Kms only and hence, we would advise you to board a direct American Airlines to your destination. You can also board an indirect flight to add a pit stop on your journey. The direct Indigo Airlines takes an average of 07:00 of time to reach the destination.
Currently, the majority of the Winnipeg to Chicago American Airlines are direct and hence, you can expect to reach your destination in a matter of a couple of hours. However, there are a few American Airlines with stopovers. You can choose to layover either at Ahmedabad or Bangalore depending upon your preference and budget.
Additionally, Winnipeg James Armstrong Richardson International Airport Winnipeg and Chicago O Hare International Airport Chicago are the nearest and major airports for your travel and if you are looking forward to saving money on your flight ticket, then a round trip is what you should go for.
EaseMyTrip is one of the largest online travel platforms in India and a trusted name in the Indian travel industry. Whether you are looking to book first class tickets or business class, premium economy, economy class tickets on Winnipeg to Chicago American Airlines, our user-friendly platform is bound to add comfort and convenience on your booking journey. You can also check out amazing offers and customize the services as per your preferences and number of passengers.
On top of this, you can enjoy amazing deals and discounts for your Winnipeg to Chicago American Airlines. With 24/7 reliable support, lower fares, airport pick-up services and first-class customer services, EaseMyTrip is definitely the go-to platform for your journey.
So, if you are looking forward to booking your flight ticket from Winnipeg (YWG) to Chicago (ORD) on American Airlines, try EaseMyTrip today.