Winnipeg to Chicago/Prospect Heights/Wheeling (YWG–PWK) — Airlines, Schedules & Connections

YWG Airport Page →
700 mi airlines charter/private 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 1 1-stop flight Verified 1w ago
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 1 hub
FLL Fort Lauderdale ~7h 43m → LF Fort Lauderdale (FLL) to Chicago/Prospect Heights/Wheeling flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Winnipeg to Chicago/Prospect Heights/Wheeling
Connecting service available through multiple hubs.
1 Airlines 700 mi 1h 29m nonstop

YWG–PWK had nonstop service, last on the schedule in June 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 700 miles in 1h 29m.

Also explore YWG Routes PWK Routes YWG Live Flights PWK Live Flights YWG Delays
All flights from Chicago/Prospect Heights/Wheeling (PWK) Chicago/Prospect Heights/Wheeling to Winnipeg flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop YWG–PWK service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
TWY TWY 1 – – 100% – –
Alliance coverage
Unaffiliated: TWY (1 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for YWG to PWK.
1-STOP
One-Stop Connections
1
Hubs
~7h
Fastest
~7h
Longest
FLL ~7h 43m
Verified with published schedule alignment and minimum connection time.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
YWG → PWK
100%
Generally reliable. Most flights run on time.
Departing
100%
Return
PWK → YWG
84%
Generally reliable. Most flights run on time.
Arriving
84%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. YWG delays →
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Chicago/Prospect Heights/Wheeling is 0 hours the same as Winnipeg.
YWG: CDT · PWK: CDT

When it's 6:00 PM in Winnipeg, it's 6:00 PM in Chicago/Prospect Heights/Wheeling.
Distance & Flight Time
700 mi / 1,126 km
Nonstop flight time is approximately 1h 29m gate to gate.
Visa & Entry

Canadian citizens do not need a visa or ESTA to enter the United States for tourism or business stays up to 6 months. A valid Canadian passport is required for air travel. Land and sea crossings also accept a NEXUS card, enhanced driver's license, or FAST card. At the border, officers determine the length of stay and may ask for proof of ties to Canada and a return plan.

Verify entry requirements with official sources before travel.
Facts

YWG–PWK Quick Facts

Key statistics for the Winnipeg to Chicago/Prospect Heights/Wheeling route.
Route details
Distance700 mi / 1,126 km
Flight time1h 29m
Time difference0 hours
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: YWG
Full nameWinnipeg / James Armstrong Richardson International Airport
IATA / ICAOYWG / CYWG
TimezoneAmerica/Winnipeg
Passengers/yr4.2M
Elevation783 ft / 239 m
Destination: PWK
Full nameChicago Executive Airport
IATA / ICAOPWK / KPWK
TimezoneAmerica/Chicago
Elevation647 ft / 197 m
FAQ

Frequently Asked Questions

Common questions about YWG to PWK flights.
Nonstop flights from Winnipeg / James Armstrong Richardson International Airport to Chicago Executive Airport take about 1h 29m gate to gate. The route covers 700 miles.
1 airline operated the nonstop from YWG to PWK. The last scheduled nonstop was in June 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in June 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 1h 29m.
Yes, 1-stop connections are available, ranked by layover time.
Yes, return flights from PWK to YWG are available. Use the direction toggle at the top to view the return schedule.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from YWG to PWK

Winnipeg / James Armstrong Richardson International Airport (YWG) and Chicago Executive Airport (PWK) had nonstop service, last on the schedule in June 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

YWG to PWK Flight Duration and Schedule

Nonstop flight time from YWG to PWK is about 1 hours 29 minutes gate to gate. The route covers a distance of 700 miles (1,126 km).

Connecting Options and Alternatives

1-stop connecting options are also available.