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

YWG Airport Page →
airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 14 1-stop flights
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 10 hubs
MSP Minneapolis 4h 23m AFAMDL → AFDLEJA Minneapolis (MSP) to Chicago flights
DEN Denver 5h 34m ACUA → WN Denver (DEN) to Chicago flights
LAS Las Vegas 9h 3m ASPWS → EJAGTWJTL Las Vegas (LAS) to Chicago flights
CUN Cancún 10h 38m WS → WN Cancún (CUN) to Chicago flights
GRR Grand Rapids ~5h 56m UA → WN Grand Rapids (GRR) to Chicago flights
PDX Portland ~6h 39m → WN Portland (PDX) to Chicago flights
ATL Atlanta ~7h 19m → AFAMDL Atlanta (ATL) to Chicago flights
FLL Fort Lauderdale ~8h 3m → EJAWN Fort Lauderdale (FLL) to Chicago flights
MCO Orlando ~8h 15m → WN Orlando (MCO) to Chicago flights
PHX Phoenix ~8h 29m → WN Phoenix (PHX) 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.

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
14
Hubs
~4h
Fastest
~11h
Longest
MSP ~4h 23m DEN ~5h 34m GRR ~5h 56m PDX ~6h 39m ATL ~7h 19m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
456
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
91%
Generally reliable. Most flights run on time.
Departing
91%
Arriving
78%
Return
MDW → YWG
49%
Frequent delays expected. Consider flexible booking.
Departing
49%
Arriving
79%
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 – 1 –
Departure OTP 91% – –
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.
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
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.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Minneapolis–Saint Paul, Denver and Harry Reid.
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.

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Minneapolis–Saint Paul, Denver and Harry Reid. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Grand Forks (GFK), Devils Lake (DVL) and International Falls (INL).