Chicago to Winnipeg (MDW–YWG) — Airlines, Schedules & Connections

MDW Airport Page →
722 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 15 1-stop flights Verified 1mo 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.

Last scheduled nonstop: May 2026.

✦ 1-Stop connections via 10 hubs
MSP Minneapolis 4h 1m DLKEVS → AMDLKE Minneapolis (MSP) to Winnipeg flights
DEN Denver 6h 7m UAWN → ACUA Denver (DEN) to Winnipeg flights
CUN Cancún 10h 21m WN → WS Cancún (CUN) to Winnipeg flights
LAS Las Vegas 11h 10m EJALXJWN → WS Las Vegas (LAS) to Winnipeg flights
GRR Grand Rapids ~5h 27m WN → Grand Rapids (GRR) to Winnipeg flights
DAL Dallas ~5h 33m EJAKOWWN → Dallas (DAL) to Winnipeg flights
YYC Calgary ~6h 55m → DEF8LA Calgary (YYC) to Winnipeg flights
ATL Atlanta ~7h 3m AFAMDL → Atlanta (ATL) to Winnipeg flights
SLC Salt Lake City ~7h 32m VJAWN → Salt Lake City (SLC) to Winnipeg flights
PSP Palm Springs ~9h 12m → Palm Springs (PSP) to Winnipeg flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Winnipeg
Connecting service available through multiple hubs.
1 Airlines 722 mi 1h 46m nonstop

MDW–YWG had nonstop service, last on the schedule in May 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 722 miles in 1h 46m.

Also explore MDW Routes YWG Routes MDW Live Flights YWG Live Flights MDW Delays YWG Delays
All flights from Winnipeg (YWG) Winnipeg to Chicago flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop MDW–YWG service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
KAI KAI 0 – – 56% – –
Alliance coverage
Unaffiliated: KAI (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for MDW to YWG.
1-STOP
One-Stop Connections
15
Hubs
~4h
Fastest
~17h
Longest
MSP ~4h 1m GRR ~5h 27m DAL ~5h 33m DEN ~6h 7m YYC ~6h 55m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
496
Candidates
Two-stop connections loaded in the connections tab above.
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
MDW → YWG
56%
Frequent delays expected. Consider flexible booking.
Departing
56%
Arriving
69%
Return
YWG → MDW
79%
Generally reliable. Most flights run on time.
Departing
79%
Arriving
79%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays → YWG delays →
Alternatives

Other ways to reach Winnipeg from Chicago

Nearby airports with service to Winnipeg / James Armstrong Richardson International Airport.
Metric MDW→YWG ORD→YWG
Distance from MDW – 15 mi
Nonstop airlines – 8
Weekly flights – 43
Flight time 1h 46m 1h 35m
Departure OTP 56% –
Chicago (ORD) to Winnipeg flights
Airports within 200 miles of MDW 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.
MDW: CDT · YWG: CDT

When it's 6:00 PM in Chicago, it's 6:00 PM in Winnipeg.
Distance & Flight Time
722 mi / 1,163 km
Nonstop flight time is approximately 1h 46m 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

MDW–YWG Quick Facts

Key statistics for the Chicago to Winnipeg route.
Route details
Distance722 mi / 1,163 km
Flight time1h 46m
Time difference0 hours
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 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 MDW to YWG flights.
Nonstop flights from Chicago Midway International Airport to Winnipeg / James Armstrong Richardson International Airport take about 1h 46m gate to gate. The route covers 722 miles.
1 airline operated the nonstop from MDW to YWG. The last scheduled nonstop was in May 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 May 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 1h 46m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Minneapolis–Saint Paul, Denver and Cancún.
Nearby alternatives include ORD. 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 MDW to YWG

Chicago Midway International Airport (MDW) and Winnipeg / James Armstrong Richardson International Airport (YWG) had nonstop service, last on the schedule in May 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.

MDW to YWG Flight Duration and Schedule

Nonstop flight time from MDW to YWG is about 1 hours 46 minutes gate to gate. The route covers a distance of 722 miles (1,163 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Minneapolis–Saint Paul, Denver and Cancún. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).