$145 Find Cheap Flights from Chicago to Winnipeg - Compare and Save

Among airlines operating Chicago 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 and Winnipeg.

Flights from Chicago to Winnipeg may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Winnipeg (YWG).

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

• Air Canada: a cabin bag and a checked bag in Economy Class
• United Airlines: a cabin 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 travelers should check the fare details before booking.

Two cabin classes are available on flights from Chicago to Winnipeg:

• Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $247 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $844 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$86 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

One-stop flights from Chicago to Winnipeg most commonly connect through:

• Minneapolis St Paul (MSP) - 40% of one-stop connections
• Toronto Pearson Intl (YYZ) - 40% of one-stop connections
• Calgary (YYC) - 16% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 4% of one-stop connections

Minneapolis St Paul (MSP) 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 to Winnipeg route. Wednesday is the cheapest departure day at $528 round-trip on average, while Monday is the most expensive at $973, a difference of $445. 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 to Winnipeg flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

These are the earliest and latest flight times available from Chicago to Winnipeg:

• Earliest: departs at 9:15 am and lands at 11:58 am
• Latest: departs at 7:54 pm and lands at 10:37 pm.

The flight takes about 2h 43m.

A nonstop flight from Chicago to Winnipeg takes 2h 43m, covering 720 miles.

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 $316 to $1,744. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Chicago to Winnipeg are currently lower than usual. Average one-way flight prices are about $236, which is 30% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 40m, 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 $18 for economy cars. Top options include:
• Thrifty
• Dollar
• Hertz
• Alamo
• Fox

Round-trip flights from Chicago to Winnipeg range from $569 to $955, with an average of $744 over the past 12 months. Anything below $569 counts as a good deal.