C$ 240 Find Cheap Flights from Winnipeg to Chicago – Compare and Save

Among airlines operating Winnipeg to Chicago O'Hare Intl Airport 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 Winnipeg and Chicago O'Hare Intl Airport.

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

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 cabin bag in Economy Class class

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

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

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 384 round-trip via Calgary (YYC), compared to C$ 954 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 34–C$ 96 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 737-700 Passenger/BBJ1 (winglets) variants.

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

• Calgary (YYC) – 75% of one-stop connections
• Minneapolis St Paul (MSP) – 17% of one-stop connections
• Toronto Pearson Intl (YYZ) – 8% of one-stop connections

Calgary (YYC) handles the largest share of one-stop connections on this route.

On the Winnipeg to Chicago O'Hare Intl Airport route, being flexible with your departure day can save you up to 48%. Saturday is the cheapest day at C$ 682 round-trip on average, while Sunday is the most expensive at C$ 1,299 – a C$ 617 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

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%.

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.

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

• Earliest: departs at 7:00 am and lands at 9:36 am
• Latest: departs at 2:15 pm and lands at 4:51 pm.

The flight takes about 2h 36m.

Last-minute fares on this route – booked within 2 weeks of departure – run 62% above the route average of C$ 772. Book 23 weeks before departure for the lowest fares.

A direct flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 36m, 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$ 408 to C$ 1,816. That means the highest observed fare was about 4x 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$ 342, which is 35% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 57m, compared with 6h 58m via Toronto Pearson Intl (YYZ) and 9h 30m via Calgary (YYC).

Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around C$ 24 for economy cars. Top options include:
• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Round-trip flights from Winnipeg to Chicago O'Hare Intl Airport range from C$ 592 to C$ 984, with an average of C$ 772 over the past 12 months. Anything below C$ 592 counts as a good deal.