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

YYC Airport Page →
airlines 0/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 68 1-stop flights
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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
Calgary to Chicago
Connecting service available through multiple hubs.
+1h ahead 68 1-stop hubs

While no nonstop service exists between YYC and MDW, connecting options are available through 68 hubs.

Also explore YYC Routes MDW Routes YYC Live Flights MDW Live Flights YYC Delays MDW Delays
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for YYC to MDW.
1-STOP
One-Stop Connections
68
Hubs
~4h
Fastest
~32h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
2,064
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 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 0 1 1
Weekly flights 0 1 –
Departure OTP 79% – –
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 connections68 hubs
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 through APA, BZN, MKE, BJC, RST, BOI, YIP, EGE, YEG, CMH, LEX, YVR, DAL, YKF, CVG, MAF, SCF, BED, HOU, MNZ, IAD, ORD, PSP, TEB, YYZ, SJC, YOW, RDU, SAT, OAK, TUS, PIE, LGA, SNA, CLD, IAH, YHU, YUL, APF, OPF, MTH, TLC, SJD, FLL, NAS, DEN, MSP, ATL, DFW, SEA, PUJ, SAN, LBG, SFO, LAS, DTW, LAX, PHX, BNA, BOS, TPA, CLT, MCO, SLC, EWR, MBJ, CUN and GDL. These options provide additional schedule flexibility.
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

68 one-stop connections are available, with the fastest taking approximately 4 hours via APA. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Edmonton (YEG) and Kalispell (FCA).