$172 Find Cheap Flights from Winnipeg to Chicago - Compare and Save

Among airlines operating Winnipeg to Chicago 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.

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).

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.

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

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $277 round-trip via Calgary (YYC), compared to $686 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$69 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

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

• Calgary (YYC) - 73% of one-stop connections
• Minneapolis St Paul (MSP) - 19% 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 route, being flexible with your departure day can save you up to 48%. Saturday is the cheapest day at $491 round-trip on average, while Sunday is the most expensive at $935: a $444 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 flights, with 100% of flights 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 are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

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

• 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 $555. Book 23 weeks before departure for the lowest fares.

A nonstop flight from Winnipeg to Chicago takes 2h 36m, 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 $294 to $1,590. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Winnipeg to Chicago are currently lower than usual. Average one-way flight prices are about $221, which is 42% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 5h 03m, compared with 6h 58m via Toronto Pearson Intl (YYZ) and 9h 30m via Calgary (YYC).

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 from around $17:

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

Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

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

Round-trip flights from Winnipeg to Chicago range from $426 to $708, with an average of $555 over the past 12 months. Anything below $426 counts as a good deal.