Cheap flights from Chicago to Winnipeg from C$ 140
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 9/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customize your resultsTrusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Winnipeg
Cheap round-trip flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
United Airlines flights from Chicago to Winnipeg
Our best United Airlines deals on Chicago to Winnipeg flight tickets
WestJet flights from Chicago to Winnipeg
Our best WestJet deals on Chicago to Winnipeg flight tickets
See travel insights to Winnipeg from
How to get the cheapest flight ticket from Chicago to Winnipeg
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Winnipeg?
What is the cheapest month to fly to Winnipeg?
The cheapest month to fly to Winnipeg from Chicago is in May. Flight prices, which tend to average around C$ 368, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around C$ 433.
What is the cheapest day to depart on your flight to Winnipeg?
Our data shows that Tuesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 435. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Saturday is C$ 985.
What is the cheapest time of day to depart on your flight to Winnipeg?
In the morning is the cheapest time of day to fly from Chicago to Winnipeg when you can find flight prices for as low as C$ 436. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly at noon, with an average ticket price of C$ 740. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Winnipeg flight route?
Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago - Winnipeg flight prices
What cabin class options are available on Chicago to Winnipeg flights?
There are 1 cabin classes available to choose from on Chicago to Winnipeg flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Winnipeg flights?
You could potentially save up to 39% on your flight if you consider stops on a Chicago to Winnipeg flight.
How many flights depart from Chicago to Winnipeg on average per day?
As of June 2025, there are 7 flights per day flying from Chicago to Winnipeg. The most common time of day flights depart is 7:00p.m., with 51% of flights taking off in the afternoon.
How many flights depart from Chicago to Winnipeg on average per week?
As of June 2025, 49 flights take off from Chicago and land in Winnipeg each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.
When to book flights from Chicago to Winnipeg
Cheap Chicago to Winnipeg (CHI to YWG) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg
How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 2h 29m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport are updated daily.
How many operators does momondo search for flights from Chicago to Winnipeg Airport?
There is 1 operator available for flights from Chicago to Winnipeg Airport as of June 2025.
How old do you have to be to fly from Chicago to Winnipeg Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Winnipeg?
Based on momondo bookings for flights between Chicago and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 83.84% of the total bookings. Other popular models include Boeing 777-300ER with 5.05%, Airbus A350-1000 with 2.02%, and Boeing 737 MAX 8 with 1.52%.
Best airlines flying from Chicago to Winnipeg
Compare and see reviews for airlines that fly from Chicago to Winnipeg with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 435 | Free Cancellation | Rating 7.1 9,553 reviews |
Air Canada Flights From Chicago to Winnipeg
Air Canada flight deals from Chicago to Winnipeg start from C$ 320 round-trip. Over the 14 Air Canada flights for this route in a normal week, average airfare is usually C$ 725 round-trip - but some users have found much cheaper deals with momondo.
Travelling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Winnipeg?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.
Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.
How can momondo help me find flights from Chicago to Winnipeg?
momondo helps you find the best flight between Chicago and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Chicago and alert you when they change.