Cheap flights from Winnipeg to Chicago from $155
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 7/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Winnipeg to Chicago
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 Winnipeg and Chicago?
What is the cheapest month to fly to Chicago?
The month of June is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $409. If you’re not able to fly to Chicago in June, then February is your next best option. Flight prices from Winnipeg to Chicago during February average around $433.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $411. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $797.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Winnipeg to Chicago during this time can be as low as $440. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $675.
What is the cheapest Winnipeg to Chicago flight route?
Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Winnipeg when booking 22 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $512 when searching 22 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Winnipeg for as low as $295 on momondo.
What cabin class options are available on Winnipeg to Chicago flights?
There are 4 cabin classes available to choose from on Winnipeg to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from Winnipeg to Chicago on average per day?
As of April 2025, 3 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 100% of daily flights taking off in the afternoon.
How many flights depart from Winnipeg to Chicago on average per week?
As of April 2025, 21 flights take off from Winnipeg and land in Chicago 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 Winnipeg to Chicago
Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago
How far is Winnipeg to Chicago by plane?
There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 21m.
When did momondo last update prices for flights from Winnipeg Airport to Chicago?
Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Chicago?
The number of operators available for flights from Winnipeg Airport to Chicago is 2 as of April 2025.
How old do you have to be to fly from Winnipeg Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Winnipeg to Chicago?
Based on momondo bookings for flights between Winnipeg and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 62.59% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 16.43%, Boeing 737 MAX 8 with 7.34%, and Airbus A330-300 with 3.15%.
What is the most popular airline from Winnipeg to Chicago?
Based on momondo bookings for flights between Winnipeg and Chicago, the leading airline is United Airlines, making up 49% of the total bookings. Other popular airlines include Air Canada with 30% and WestJet with 21%.
Best airlines flying from Winnipeg to Chicago
Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $239 | Free Cancellation | Rating 7.0 9,118 reviews | |||
| PriceFrom $443 | Free Cancellation | Rating 7.4 8,656 reviews |
United Airlines Flights From Winnipeg to Chicago
United Airlines flight deals from Winnipeg to Chicago start from $443 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $547 round-trip - but some users have found much cheaper deals with momondo.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.0/10 from 9,118 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $572, with deals from around $239 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Winnipeg to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.
Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Winnipeg to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.