$203 Find Cheap Flights from Winnipeg to Chicago - Compare and Save

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

• Earliest: departs at 8:00 am and lands at 10:42 am
• Latest: departs at 3:15 pm and lands at 5:57 pm.

The flight takes about 2h 42m.

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

• Economy Class
• Business Class
• First Class

A nonstop flight from Winnipeg to Chicago takes 2h 42m, 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.

Round-trip flights from Winnipeg to Chicago range from $455 to $740, with an average of $610 over the past 12 months. Anything below $455 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 50% above the $610 route average. Book 23 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $300 round-trip via Calgary (YYC), compared to $691 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Afternoon is the busiest departure period on Winnipeg to Chicago flights, with 100% of flights 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 $405 to $1,120. That means the highest observed fare was about 3x higher than the lowest one.

One-way fares from Winnipeg to Chicago are currently lower than usual. Average one-way flight prices are about $317, which is 19% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

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

Near Chicago Midway Airport (MDW) — daily rates averaging $84:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

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

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

• Calgary (YYC) - 67% of one-stop connections
• Minneapolis St Paul (MSP) - 24% of one-stop connections
• Toronto Pearson Intl (YYZ) - 9% of one-stop connections

Yes. Flexible dates can save you up to 37% on flights from Winnipeg to Chicago. Wednesday is the cheapest departure day at $561 round-trip on average, while Sunday is the most expensive at $881, a difference of $320.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only United Airlines operates flights between Winnipeg and Chicago.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 5h 10m, compared with 7h 36m via Toronto Pearson Intl (YYZ) and 9h 15m via Calgary (YYC).

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Winnipeg to Chicago flights:

• Air Canada: offers free seat selection
• 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 cabin bag and a checked bag in Economy Class
• United Airlines: a cabin bag and a checked bag in First Class

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