By clicking, I agree to the terms

Winnipeg to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Winnipeg to Chicago

Departure Arrival Travel dates Round-trip
YWG CHI Fri, Oct 3 - Sun, Oct 5 $460
YWG CHI Thu, Sep 11 - Sun, Sep 14 $461
YWG CHI Sun, Aug 31 - Tue, Sep 2 $508
YWG CHI Sun, Aug 31 - Tue, Sep 2 $722

Winnipeg and Chicago airports and terminals

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 YWG to CHI

    Carriers
    Air Canada, United Airlines
Back to menu Return to top

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from YWG to ORD

    Terminal Carriers
    Terminal 1 Air Canada, United Airlines
    Terminal 2 Air Canada, United Airlines
Back to menu Return to top

Cheap flights from Winnipeg to Chicago

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 26 27 28 29 30
31
$486

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 165 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 68 reviews

6500 SOUTH CICERO AVE Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 22 reviews

6530 S. Cicero Avenue Map

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 30 reviews

6540 S. Cicero Ave. Map

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.6 / 5 11 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $99

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 146 reviews

6501 N. Mannheim Road Map

Save 15% on your stay, Breakfast Included

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

August

Cheapest weekend flights in August from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 1 Winnipeg (YWG) Chicago (ORD) Air Canada $643
Earn $6.43
Return Sun, Aug 3 Chicago (ORD) Winnipeg (YWG) Air Canada

Lowest roundtrip airfare in August from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Aug 31 Winnipeg (YWG) Chicago (ORD) United Airlines $486
Earn $4.86
Return Tue, Sep 2 Chicago (ORD) Winnipeg (YWG) United Airlines

Best one-week trip in August from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Aug 4 Winnipeg (YWG) Chicago (ORD) Air Canada $586
Earn $5.86
Return Mon, Aug 11 Chicago (ORD) Winnipeg (YWG) Air Canada
Back to menu Return to top

September

Cheapest weekend flights in September from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 11 Winnipeg (YWG) Chicago (ORD) United Airlines $461
Earn $4.61
Return Sun, Sep 14 Chicago (ORD) Winnipeg (YWG) United Airlines

Lowest roundtrip airfare in September from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 11 Winnipeg (YWG) Chicago (ORD) United Airlines $461
Earn $4.61
Return Sun, Sep 14 Chicago (ORD) Winnipeg (YWG) United Airlines
Back to menu Return to top

October

Cheapest weekend flights in October from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 3 Winnipeg (YWG) Chicago (ORD) Air Canada $460
Earn $4.60
Return Sun, Oct 5 Chicago (ORD) Winnipeg (YWG) Air Canada

Lowest roundtrip airfare in October from Winnipeg to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 3 Winnipeg (YWG) Chicago (ORD) Air Canada $460
Earn $4.60
Return Sun, Oct 5 Chicago (ORD) Winnipeg (YWG) Air Canada
Back to menu Return to top

Flights to Chicago

James Armstrong Richardson International Airport in Winnipeg, MN

Twenty airlines provide international and domestic flights from the James Armstrong Richardson International Airport, which is the main airport that serves Winnipeg, Manitoba, Canada. Cheap flights from Winnipeg that are available through Orbitz.com usually depart from this major airport.

Parking at James Armstrong Richardson Airport

There are two parking facilities at James Armstrong Richardson Airport. One is a large economy lot with lower prices for long-term parking, and the other is smaller and known as the Parkade. You can treat yourself to valet parking for an extra 25 Canadian dollars at the Parkade, where the fees are 20 Canadian dollars per day and 90 dollars per week. Weekly fees are 75 Canadian dollars and daily fees are 15 dollars at the economy lot, and the short-term parking fee at either lot is two Canadian dollars per half-hour.

Transportation to James Armstrong Richardson Airport

Winnipeg Transit operates city buses from various points in Winnipeg to the airport. Bus tickets are available from authorized vendors for 2.15 Canadian dollars, or you can pay 2.45 dollars cash on the bus itself. A private shuttle is also available from the town of Brandon for 48 Canadian dollars. Unicity is the official airport taxi service, and its rates range from 9.25 to 32 Canadian dollars depending on the distance traveled. Limousines and private shuttles are also available. Whether you choose the bargain bus or a luxury limousine, you can relax on your way to the airport knowing everything is ready for you when you book your tickets and other travel needs through Orbitz.com.

Restaurants at James Armstrong Richardson Airport

There are nine dining options at this airport, including Starbucks Coffee, T.G.I. Friday's, Tim Hortons, a local pizzeria, a bar and an Oriental fast-food restaurant. This gives you a wide choice of food and drink to enjoy before you board the flight that you selected from the cheap flights from Winnipeg that are featured on Orbitz.com.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Interesting facts about flights from Winnipeg to Chicago

    • 8 direct flights are operating from Winnipeg to Chicago today.
    • Today's average time for a direct flight is 2h 9m.
    • Air Canada flight 4499 (1:00 AM GMT, Canadair Regional Jet) is today's earliest available flight from Winnipeg to Chicago.
    • Air Canada flight 3197 (10:08 AM GMT, Embraer RJ135/RJ140/RJ145) is today's latest available flight from Winnipeg to Chicago.
    • Today's shortest direct flight from Winnipeg to Chicago (Air Canada flight 3071, Embraer RJ135/RJ140/RJ145) takes 2h 8m.
    • Today's longest direct flight from Winnipeg to Chicago (Air Canada flight 4499, Canadair Regional Jet) takes 2h 12m.
    • Flights from Winnipeg Airport (YWG) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between Winnipeg and Chicago

Equipment Carrier
Embraer RJ135/RJ140/RJ145 United Airlines, Air Canada
Canadair Regional Jet 700 United Airlines, Air Canada
Canadair Regional Jet United Airlines, Air Canada