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

MDW Airport Page →
722 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 48 1-stop flights Verified 1h ago
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  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Winnipeg
1 carrier, 1 flights/week nonstop.
1 Airlines 1 Flights/wk 722 mi 2h 50m nonstop 48 1-stop hubs

MDW–YWG is served by 1 airline with nonstop service. KAI leads the route. The flight covers 722 miles in approximately 2h 50m. Beyond nonstop, 48 hubs offer 1-stop connections.

Also explore MDW Routes YWG Routes MDW Live Flights YWG Live Flights MDW Delays YWG Delays
Carriers on this route

Airline Landscape

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for MDW to YWG.
1-STOP
One-Stop Connections
48
Hubs
~3h
Fastest
~19h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
651
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.
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 1 3
Weekly flights 1 28
Flight time 2h 50m 2h 34m
Departure OTP 100% –
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 2h 50m.
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 time2h 50m
Time difference0 hours
Airlines (nonstop)1
Weekly flights1 out
1-stop connections48 hubs
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 approximately 2h 50m. The route covers 722 miles.
1 airline operates nonstop service: KAI.
There are approximately 1 nonstop flights per week from MDW to YWG.
Yes, 1-stop connections are available through PWK, RST, STP, OMA, YQG, CLE, SDF, ORD, YYZ, DAL, YOW, BNA, STL, YVR, YHU, ASE, JFK, YEG, YYC, EWR, ATL, AUS, SLC, SRQ, APF, APC, YLW, MCO, PHX, SCF, SNA, FLL, PSP, LAX, MIA, GCM, CUN, UDD, SFO, PLS, SJD, MBJ, LIR, MSP, PUJ, SXM, LAS and DEN. These options provide additional schedule flexibility.
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) are connected by nonstop service from KAI. With 1 weekly departures, this is a regularly served route.

MDW to YWG Flight Duration and Schedule

Nonstop flight time from MDW to YWG ranges from 2 hours 50 minutes. The route covers a distance of 722 miles (1,163 km).

Connecting Options and Alternatives

48 one-stop connections are available, with the fastest taking approximately 3 hours via PWK. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).