Flights from Chicago to Winnipeg

Selected fares from Chicago to Winnipeg

Departure Arrival Travel dates Round-trip
CHI YWG Sat, Nov 7 - Mon, Nov 9 $443
CHI YWG Sat, Nov 7 - Mon, Nov 9 $486
CHI YWG Thu, Sep 17 - Tue, Sep 22 $487
CHI YWG Fri, Nov 6 - Sun, Nov 8 $681
Sun Mon Tue Wed Thu Fri Sat
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25
$495
26 27 28
$495
29
30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Chicago and Winnipeg airports and terminals

Airports in Chicago IL, US

map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from ORD to YWG

    Terminal Carriers
    Terminal 1 Air Canada, United Airlines
    Terminal 2 Air Canada, United Airlines
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Airports in Winnipeg MB, CA

map of airports in Winnipeg
  • 1

    Winnipeg Airport (YWG)

    Distance from City Center: 3.8 miles

    Carriers for flights from CHI to YWG

    Carriers
    Air Canada, United Airlines
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Featured Winnipeg Airport Hotels

From $102

Four Points by Sheraton Winnipeg International Airport

3 stars
3.7 / 5 3 reviews

1999 Wellington Avenue Map

Save 15% on your stay, Breakfast Included

Four Points by Sheraton Winnipeg International Airport is the only hotel adjacent to the Winnipeg James Armstrong Richardson International Airport (YWG).... More

From $86

Hilton Winnipeg Airport Suites

3 stars
4.3 / 5 26 reviews

1800 Wellington Avenue Map

Includes parking for up to 7 nights

Enjoy the spacious rooms and convenient location of the Hilton Winnipeg Airport Suites hotel.... More

From $124

Victoria Inn Airport Conf Ctr

3 stars
4.0 / 5 6 reviews

1808 Wellington Avenue Map

...and 24-hour airport shuttle.... More

From $89

Hampton Inn by Hilton Winnipeg Airport/Polo Park

2 stars
5.0 / 5 3 reviews

730 Berry Street Map

Free On The House hot breakfast, Wi-Fi

Hampton Inn by Hilton Winnipeg Airport/Polo Park is located just 2 minutes from Winnipeg International Airport.... More

From $77

Days Inn & Suites Winnipeg Airport, Manitoba

2 stars
4.0 / 5 3 reviews

695 Berry Street Map

Stay 3, Save 20%

For excellent value and first-rate accommodations, stay at the newly built Days Inn and Suites Winnipeg Airport hotel.... More

August

Cheapest weekend flights in August from Chicago to Winnipeg

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 28 Chicago (ORD) Winnipeg (YWG) Air Canada $495
Earn $4.95
Return Mon, Aug 31 Winnipeg (YWG) Chicago (ORD) Air Canada

Lowest roundtrip airfare in August from Chicago to Winnipeg

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Aug 25 Chicago (ORD) Winnipeg (YWG) Air Canada $495
Earn $4.95
Return Tue, Sep 1 Winnipeg (YWG) Chicago (ORD) Air Canada

Best one-week trip in August from Chicago to Winnipeg

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Aug 25 Chicago (ORD) Winnipeg (YWG) Air Canada $495
Earn $4.95
Return Tue, Sep 1 Winnipeg (YWG) Chicago (ORD) Air Canada
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September

Lowest roundtrip airfare in September from Chicago to Winnipeg

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 17 Chicago (ORD) Winnipeg (YWG) Air Canada $487
Earn $4.87
Return Tue, Sep 22 Winnipeg (YWG) Chicago (ORD) Air Canada
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October

Cheapest weekend flights in October from Chicago to Winnipeg

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 8 Chicago (ORD) Winnipeg (YWG) Delta Air Lines $443
Earn $4.43
Return Mon, Oct 12 Winnipeg (YWG) Chicago (ORD) Delta Air Lines

Lowest roundtrip airfare in October from Chicago to Winnipeg

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 8 Chicago (ORD) Winnipeg (YWG) Delta Air Lines $443
Earn $4.43
Return Mon, Oct 12 Winnipeg (YWG) Chicago (ORD) Delta Air Lines
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Flights 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.

Interesting facts about flights from Chicago to Winnipeg

    • 6 direct flights are operating from Chicago to Winnipeg today.
    • Today's average time for a direct flight is 2h 8m.
    • Air Canada flight 4463 (9:07 AM GMT, Canadair Regional Jet 700) is today's earliest available flight from Chicago to Winnipeg.
    • Air Canada flight 3381 (7:36 PM GMT, Embraer RJ135/RJ140/RJ145) is today's latest available flight from Chicago to Winnipeg.
    • Today's shortest direct flight from Chicago to Winnipeg (Air Canada flight 4463, Canadair Regional Jet 700) takes 2h 7m.
    • Today's longest direct flight from Chicago to Winnipeg (Air Canada flight 3381, Embraer RJ135/RJ140/RJ145) takes 2h 11m.
    • Flights from Midway Airport (MDW), O'Hare International Airport (ORD) to Winnipeg Airport (YWG) are available for this route.