C$ 210 Find Cheap Flights from Chicago to Winnipeg – Compare and Save

Among airlines operating Chicago O'Hare Intl Airport to Winnipeg flights:

• Air Canada: offers free seat selection
• United Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only United Airlines operates flights between Chicago O'Hare Intl Airport and Winnipeg.

Flights from Chicago O'Hare Intl Airport to Winnipeg usually depart from Chicago O'Hare Intl (ORD) and arrive at Winnipeg (YWG).

Here are some options for this route, based on selected ticket types and cabin classes:

• Air Canada: a carry-on bag and a checked bag in Economy Class
• United Airlines: a carry-on bag and a checked bag in Economy Class
• Air New Zealand: a carry-on bag and a checked bag in First Class

Bag allowance can vary by ticket type, cabin class, route, and airline, so travellers should check the fare details before booking.

Two cabin classes are available on flights from Chicago O'Hare Intl Airport to Winnipeg:

• Economy Class
• First Class

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 611 round-trip via Calgary (YYC), compared to C$ 1,164 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 55–C$ 119 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

The Embraer 175 (Enhanced Winglets) family is used most often on this route, operated mainly by Air Canada and United Airlines. Other aircraft seen on the route include Boeing 777-300 variants.

One-stop flights from Chicago O'Hare Intl Airport to Winnipeg most commonly connect through:

• Toronto Pearson Intl (YYZ) – 43% of one-stop connections
• Minneapolis St Paul (MSP) – 39% of one-stop connections
• Calgary (YYC) – 17% of one-stop connections

Toronto Pearson Intl (YYZ) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 46% on the Chicago O'Hare Intl Airport to Winnipeg route. Wednesday is the cheapest departure day at C$ 728 round-trip on average, while Monday is the most expensive at C$ 1,342, a difference of C$ 614. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Chicago O'Hare Intl Airport to Winnipeg flights, with 50% leaving in that window. Evening departures account for 50%, Afternoon flights for 0%, and Night flights for 0%.

These are the earliest and latest flight times available from Chicago O'Hare Intl Airport to Winnipeg:

• Earliest: departs at 9:15 am and lands at 11:57 am
• Latest: departs at 7:54 pm and lands at 10:36 pm.

The flight takes about 2h 42m.

A direct flight from Chicago O'Hare Intl Airport to Winnipeg takes 2h 42m, covering 1,829 km.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 454 to C$ 1,996. That means the highest observed fare was about 4x higher than the lowest one.

One-way fares from Chicago O'Hare Intl Airport to Winnipeg are currently lower than usual. Average one-way flight prices are about C$ 234, which is 50% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 36m, compared with 6h 56m via Toronto Pearson Intl (YYZ) and 9h 47m via Calgary (YYC).

Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates starting from around C$ 25 for economy cars. Top options include:
· Thrifty
· Dollar
· Hertz
· Alamo
· Fox

Round-trip flights from Chicago O'Hare Intl Airport to Winnipeg range from C$ 829 to C$ 1,328, with an average of C$ 1,051 over the past 12 months. Anything below C$ 829 counts as a good deal.