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

YWG Airport Page →
722 mi airlines charter/private 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 5 1-stop flights Verified 2w 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 connections via 5 hubs
MSP Minneapolis 3h 45m AFAMDL → AFDLWN Minneapolis (MSP) to Chicago flights
ORD Chicago 5h 4m ACAVCM → UA Chicago (ORD) to Chicago flights
DEN Denver 6h ACUA → WN Denver (DEN) to Chicago flights
LAS Las Vegas 7h 55m WS → DLEJALXJ Las Vegas (LAS) to Chicago flights
CUN Cancún 11h 19m WS → WN Cancún (CUN) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Winnipeg to Chicago
Connecting service available through multiple hubs.
722 mi 1h 54m nonstop

While no nonstop service exists between YWG and MDW, 1-stop connecting options are available.

Also explore YWG Routes MDW Routes YWG Live Flights MDW Live Flights YWG Delays MDW Delays
All flights from Chicago (MDW) Chicago to Winnipeg flights
Connections

Connection Landscape

1-stop and 2-stop options for YWG to MDW.
1-STOP
One-Stop Connections
5
Hubs
~3h
Fastest
~11h
Longest
MSP ~3h 45m ORD ~5h 4m DEN ~6h 0m LAS ~7h 55m CUN ~11h 19m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
442
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
YWG → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
100%
Return
MDW → YWG
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
100%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. YWG delays → MDW delays →
Alternatives

Other ways to reach Chicago from Winnipeg

Nearby airports with service to Chicago Midway International Airport.
Metric YWG→MDW GFK→MDW DVL→MDW
Distance from YWG – 136 mi 145 mi
Nonstop airlines – 1 1
Weekly flights – – –
Flight time 1h 54m 1h 33m 1h 45m
Departure OTP 100% – –
Grand Forks (GFK) to Chicago flights · Devils Lake (DVL) to Chicago flights · International Falls (INL) to Chicago flights
Airports within 200 miles of YWG with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Chicago is 0 hours the same as Winnipeg.
YWG: CDT · MDW: CDT

When it's 6:00 PM in Winnipeg, it's 6:00 PM in Chicago.
Distance & Flight Time
722 mi / 1,163 km
Nonstop flight time is approximately 1h 54m 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–MDW Quick Facts

Key statistics for the Winnipeg to Chicago route.
Route details
Distance722 mi / 1,163 km
Flight time1h 54m
Time difference0 hours
Airlines (nonstop)0
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: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about YWG to MDW flights.
Nonstop flights from Winnipeg / James Armstrong Richardson International Airport to Chicago Midway International Airport take about 1h 54m gate to gate. The route covers 722 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Minneapolis–Saint Paul, Chicago O'Hare and Denver.
Yes, return flights from MDW to YWG are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include GFK, DVL and INL. 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 YWG to MDW

Winnipeg / James Armstrong Richardson International Airport (YWG) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

YWG to MDW Flight Duration and Schedule

Nonstop flight time from YWG to MDW is about 1 hours 54 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, Chicago O'Hare and Denver. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Grand Forks (GFK), Devils Lake (DVL) and International Falls (INL).