Calgary to Chicago (YYC–MDW) — Airlines, Schedules & Connections

YYC Airport Page →
airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 35 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 5h 15m AFDLKE → AFDLWN Minneapolis (MSP) to Chicago flights
DTW Detroit 5h 55m WS → AFDLKE Detroit (DTW) to Chicago flights
DEN Denver 6h 9m ACUAWS → WN Denver (DEN) to Chicago flights
BNA Nashville 6h 30m JRTWS → WN Nashville (BNA) to Chicago flights
SEA Seattle 7h 6m ASAYEK → WN Seattle (SEA) to Chicago flights
ATL Atlanta 7h 15m WS → AFAMDL Atlanta (ATL) to Chicago flights
DFW Dallas-Fort Worth 7h 24m AAAYBA → F9Y4 Dallas-Fort Worth (DFW) to Chicago flights
LAS Las Vegas 7h 41m KEWS → EJAGTWJTL Las Vegas (LAS) to Chicago flights
PHX Phoenix 8h WS → WN Phoenix (PHX) to Chicago flights
SLC Salt Lake City 8h 45m AFDLLA → WN Salt Lake City (SLC) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Calgary to Chicago
Connecting service available through multiple hubs.
+1h ahead

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

Also explore YYC Routes MDW Routes YYC Live Flights MDW Live Flights YYC Delays MDW Delays
All flights from Chicago (MDW) Chicago to Calgary flights
Connections

Connection Landscape

1-stop and 2-stop options for YYC to MDW.
1-STOP
One-Stop Connections
35
Hubs
~5h
Fastest
~32h
Longest
MSP ~5h 15m DTW ~5h 55m CMH ~6h 5m DEN ~6h 9m DAL ~6h 24m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
2,010
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
YYC → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
85%
Return
MDW → YYC
28%
Frequent delays expected. Consider flexible booking.
Departing
28%
Arriving
94%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. YYC delays → MDW delays →
Alternatives

Other ways to reach Chicago from Calgary

Nearby airports with service to Chicago Midway International Airport.
Metric YYC→MDW YEG→MDW FCA→MDW
Distance from YYC – 152 mi 194 mi
Nonstop airlines – 1 2
Weekly flights – 1 1
Departure OTP 100% – –
Edmonton (YEG) to Chicago flights · Kalispell (FCA) to Chicago flights
Airports within 200 miles of YYC with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+1h
Chicago is 1 hour ahead of Calgary.
YYC: MDT · MDW: CDT

When it's 6:00 PM in Calgary, it's 7:00 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

YYC–MDW Quick Facts

Key statistics for the Calgary to Chicago route.
Route details
Time difference+1 hour
Airlines (nonstop)0
1-stop connectionsAvailable
Origin: YYC
Full nameCalgary International Airport
IATA / ICAOYYC / CYYC
TimezoneAmerica/Edmonton
Passengers/yr18.0M
Elevation3,557 ft / 1,084 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 YYC to MDW flights.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Minneapolis–Saint Paul, Detroit Metropolitan Wayne County and Denver.
Chicago is 1 hour ahead of Calgary.
Yes, return flights from MDW to YYC are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include YEG and FCA. 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, Detroit Metropolitan Wayne County and Denver. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Edmonton (YEG) and Kalispell (FCA).