C$ 271 Find Cheap Flights from Winnipeg to Chicago – Compare and Save

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

• Earliest: departs at 8:00 am and lands at 10:44 am
• Latest: departs at 3:15 pm and lands at 5:59 pm.

The flight takes about 2h 44m.

Only Economy Class is available on flights from Winnipeg to Chicago O'Hare Intl Airport.

A direct flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 44m, 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.

Round-trip flights from Winnipeg to Chicago O'Hare Intl Airport range from C$ 680 to C$ 1,075, with an average of C$ 896 over the past 12 months. Anything below C$ 680 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 43% above the C$ 896 route average. Book 23 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 442 round-trip via Calgary (YYC), compared to C$ 996 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 36–C$ 143 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 737 MAX 8 variants.

Afternoon is the busiest departure period on Winnipeg to Chicago O'Hare Intl Airport flights, with 100% leaving in that window. Morning departures account for 0%, Evening flights for 0%, and Night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 528 to C$ 1,790. That means the highest observed fare was about 3x higher than the lowest one.

One-way fares from Winnipeg to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about C$ 396, which is 30% below the typical average for this route.

Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates averaging C$ 90 for economy cars. Top options include:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

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

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

• Calgary (YYC) – 74% of one-stop connections
• Minneapolis St Paul (MSP) – 15% of one-stop connections
• Toronto Pearson Intl (YYZ) – 9% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) – 2% of one-stop connections

Yes. Flexible dates can save you up to 37% on flights from Winnipeg to Chicago O'Hare Intl Airport. Tuesday is the cheapest departure day at C$ 800 round-trip on average, while Sunday is the most expensive at C$ 1,256, a difference of C$ 456.

KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

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

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 45m, compared with 7h 48m via Toronto Pearson Intl (YYZ) and 9h 24m via Calgary (YYC).

Chicago O'Hare Intl Airport is 1 hour behind Winnipeg (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

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

• United Airlines: offers free seat selection

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

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 Business Class
• United Airlines: a cabin bag in Economy Class class

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