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Fares from $204 One Way, $414 Round Trip from Chicago to Winnipeg

Prices starting at $414 for return flights and $204 for one-way flights to Winnipeg were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Need A Hotel In Winnipeg?

Hotels In Top Winnipeg Neighborhoods

Fort Gary
22 hotels
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$75

Humphry Inn & Suites

2.5 out of 5.0
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Mere Hotel

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Stay Near Exciting Winnipeg Attractions

More About Flying To Winnipeg from Chicago

Route Information for Flights from Chicago to Winnipeg

Origin Airport IATA CodeCHI
Destination Airport IATA CodeYWG
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Plan Your Trip from Chicago to Winnipeg

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Winnipeg James Armstrong Richardson International Airport

Whether you are looking for cheap flights to Winnipeg, accommodations in the Winnipeg area, or vacation packages in Manitoba, Canada, Orbitz.com can get you a great deal. Winnipeg James Armstrong Richardson International Airport serves the Winnipeg area and acts as an air hub to more isolated areas in northern Canada, such as Saskatchewan. Airlines served by this airport include Air Canada, Delta Connection, United Express, and Sunwing Airlines.

Airport Transportation Information

Unicity Taxi is the exclusive taxi service for the Winnipeg James Armstrong Richardson International Airport. Taxi rates are typically between $15 and $18 from the airport to the city. Limousine services and hotel shuttles are also popular options for travelers arriving at this airport. For travelers on a budget, Winnipeg Transit operates public buses that go from the airport to various areas of the city. You can also use Orbitz.com to find and book a car from one of the car rental companies in the airport, such as Avis, Enterprise, Hertz, or National Car Rental.

Weather in Winnipeg

Winters in Winnipeg are cold and dry, with below-zero temperatures in January and February being the norm. The average high in the summer months ranges from 73 to 79 degrees Fahrenheit, and lows drop into the 50s, even in midsummer. Winnipeg skies tend to be clear, and the city only gets about 20 inches of precipitation a year.

Winnipeg Activities and Events

Art lovers will enjoy exploring the Winnipeg Art Gallery and the art galleries and historic architecture of the Exchange District National Historic Site. Those interested in history may want to check out the Manitoba Museum, while nature lovers should head to the Bison Safari adventure at FortWhyte Alive. Winnipeg is also home to a multitude of festivals, including the Winnipeg Fringe Festival in July and Folklorama in August. No matter what your preferred activity, rely on Orbitz.com for cheap flights to Winnipeg.

Flights from Chicago to Winnipeg - Frequently Asked Questions

Are there non-stop flights from Chicago to Winnipeg?

Have your passport at the ready, because United Airlines will take you directly from Chicago to Winnipeg. Book your ticket now and enjoy a relaxing, nonstop flight.

What is the shortest flight from Chicago to Winnipeg?

If the weather is good and everything goes to plan, you could be flying into Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) from Chicago, IL (ORD-O'Hare Intl.) in just 2 hours and 21 minutes. With such a short flight time, think about bringing just hand luggage.

What airlines fly from Chicago (and vicinity) to Winnipeg (and vicinity) most frequently?

If you're looking for the airline with the most flights from Chicago (and vicinity) to Winnipeg (and vicinity), United Airlines is your best bet. This renowned carrier operates 40 flights along this route per month.

If I am not able to travel due to COVID-19, can I cancel my flight to Winnipeg?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Winnipeg have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Winnipeg with flexible change policies?

In most cases you'll have the option to reschedule your flight to Winnipeg without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.