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

PWK Airport Page →
700 mi airlines charter/private 1/wk
On-time Some delays Frequent delays
Flight Schedule No service Verified 15m ago
Also flown by charter / private operators.
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 More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago/Prospect Heights/Wheeling to Winnipeg
Connecting service available through multiple hubs.
1 Airlines 700 mi 1h 32m nonstop

PWK–YWG 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 32m.

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

Airline Landscape

Carriers that operated nonstop PWK–YWG service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
TWY TWY 1 – – – – –
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 PWK to YWG.
1-STOP
One-Stop Connections
0
Hubs
–
Fastest
–
Longest
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
PWK → YWG
100%
Generally reliable. Most flights run on time.
Arriving
100%
Return
YWG → PWK
100%
Generally reliable. Most flights run on time.
Departing
100%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. YWG delays →
Alternatives

Other ways to reach Winnipeg from Chicago/Prospect Heights/Wheeling

Nearby airports with service to Winnipeg / James Armstrong Richardson International Airport.
Metric PWK→YWG ORD→YWG MDW→YWG
Distance from PWK – 9 mi 24 mi
Nonstop airlines – 8 3
Weekly flights – 43 –
Flight time 1h 32m 1h 35m 1h 46m
Chicago (ORD) to Winnipeg flights · Chicago (MDW) to Winnipeg flights
Airports within 200 miles of PWK with service to Winnipeg / James Armstrong Richardson International Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago/Prospect Heights/Wheeling, it's 6:00 PM in Winnipeg.
Distance & Flight Time
700 mi / 1,126 km
Nonstop flight time is approximately 1h 32m gate to gate.
Visa & Entry

US passport holders enter Canada without a visa for stays up to 6 months. No eTA is needed when arriving by air with a US passport. Passport must be valid for the duration of the stay. A return or onward ticket and proof of funds may be requested at the border.

Verify entry requirements with official sources before travel.
Facts

PWK–YWG Quick Facts

Key statistics for the Chicago/Prospect Heights/Wheeling to Winnipeg route.
Route details
Distance700 mi / 1,126 km
Flight time1h 32m
Time difference0 hours
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: PWK
Full nameChicago Executive Airport
IATA / ICAOPWK / KPWK
TimezoneAmerica/Chicago
Elevation647 ft / 197 m
Destination: YWG
Full nameWinnipeg / James Armstrong Richardson International Airport
IATA / ICAOYWG / CYWG
TimezoneAmerica/Winnipeg
Passengers/yr4.2M
Elevation783 ft / 239 m
FAQ

Frequently Asked Questions

Common questions about PWK to YWG flights.
Nonstop flights from Chicago Executive Airport to Winnipeg / James Armstrong Richardson International Airport take about 1h 32m gate to gate. The route covers 700 miles.
1 airline operated the nonstop from PWK to YWG. 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 32m.
Yes, 1-stop connections are available, ranked by layover time.
Yes, return flights from YWG to PWK are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD and MDW. See the Alternatives section for a full comparison.
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 PWK to YWG

Chicago Executive Airport (PWK) and Winnipeg / James Armstrong Richardson International Airport (YWG) 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.

PWK to YWG Flight Duration and Schedule

Nonstop flight time from PWK to YWG is about 1 hours 32 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. Nearby alternative airports include Chicago (ORD) and Chicago (MDW).