Unable to find information about the schedule of direct flights from
Helping travelers to find the best flight offers
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Winnipeg. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A direct flight is the most convenient and comfortable way to fly from Chicago to Winnipeg, despite the fact that sometimes flights with transfers can cost significantly less.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Winnipeg:
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We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Unable to find information about the schedule of direct flights from
The cheapest one-way flight from Chicago to Winnipeg departs on 12/29/2025, is operated by United Airlines and costs $307
The cheapest roundtrip flight from Chicago to Winnipeg departs on 01/15/2026, is operated by Frontier Airlines and costs $246
Fastest flight from Chicago to Winnipeg takes 11h 21m
There are no direct flights on this route.
The distance between Chicago and Winnipeg is 1154km (715 miles). There are 16 direct flights from Chicago to Winnipeg. Chicago and Winnipeg are in the same time zone. Flights from Chicago begin at 9:22 AM. The latest flight from Chicago departs at 9:22 AM
Chicago — Winnipeg
12/29/2025
Departure
Direct flight
UA5475
Starting at $322
Starting at $307
The route Chicago — Winnipeg is served by a single airline — United Airlines. This means that when planning your trip, you won’t need to spend time choosing between dozens of carriers: all flights are operated by one provider, which simplifies the booking process. Despite the limited choice, passengers can still plan ahead, select optimal departure dates, and buy tickets at the lowest price — from $307. Using our service, you can quickly compare available United Airlines flights and book a seat in advance at a favorable rate.
We couldn't find any special offers for flights from Chicago to Winnipeg
The cheapest flight ticket from Chicago to Winnipeg according to data for the last 48 hours costs $307
Often the best time to buy tickets from Chicago to Winnipeg is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Winnipeg can be found flying in these months: December.
The fastest flights from Chicago to Winnipeg start from 11 hours 21 minutes in the air.
The following airlines operate direct flights on the route Chicago — Winnipeg: United Airlines
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Winnipeg