Key West to Chicago (EYW–MDW) — Airlines, Schedules & Connections

EYW Airport Page →
1,239 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 60 1-stop flights Verified 34m 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
Key West to Chicago
Connecting service available through multiple hubs.
1 Flights/wk 1,239 mi 3h 2m nonstop -1h behind 60 1-stop hubs

While no nonstop service exists between EYW and MDW, connecting options are available through 60 hubs.

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for EYW to MDW.
1-STOP
One-Stop Connections
60
Hubs
~3h
Fastest
~23h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,459
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 Key West

Nearby airports with service to Chicago Midway International Airport.
Metric EYW→MDW MIA→MDW OPF→MDW
Distance from EYW – 126 mi 131 mi
Nonstop airlines 0 12 7
Weekly flights 1 18 4
Flight time 3h 2m 2h 38m 2h 48m
Miami (MIA) to Chicago flights · Miami (OPF) to Chicago flights · Fort Myers (RSW) to Chicago flights
Airports within 200 miles of EYW 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 behind Key West.
EYW: EDT · MDW: CDT

When it's 6:00 PM in Key West, it's 5:00 PM in Chicago.
Distance & Flight Time
1,239 mi / 1,994 km
Nonstop flight time is approximately 3h 2m.
Facts

EYW–MDW Quick Facts

Key statistics for the Key West to Chicago route.
Route details
Distance1,239 mi / 1,994 km
Flight time3h 2m
Time difference-1 hour
Airlines (nonstop)0
Weekly flights1 out / 1 return
1-stop connections60 hubs
Origin: EYW
Full nameKey West International Airport
IATA / ICAOEYW / KEYW
TimezoneAmerica/New_York
Passengers/yr1.5M
Elevation3 ft / 1 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 EYW to MDW flights.
Nonstop flights from Key West International Airport to Chicago Midway International Airport take approximately 3h 2m. The route covers 1,239 miles.
There are approximately 1 nonstop flights per week from EYW to MDW. The return direction has about 1 weekly flights.
Yes, 1-stop connections are available through STL, PNS, MSY, RSW, ORL, SRQ, JAX, PIE, MTH, LCK, SDF, SUA, MCN, CLE, AVL, TYS, MKE, CHS, MCI, TUL, MNZ, CMH, RIC, ORD, NAS, ORF, SAV, BWI, IAD, HOU, PBI, DAL, SYR, OMA, HVN, AUS, PVD, OKC, IAH, FLL, EIS, SXM, LAS, BUR, RDU, TPA, BNA, MCO, CVG, ATL, CLT, MIA, PIT, LGA, EWR, BOS, DCA, PHL, DFW and IND. These options provide additional schedule flexibility.
Chicago is 1 hour behind Key West.
Yes, return flights from MDW to EYW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include MIA, OPF and RSW. 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 EYW to MDW

Key West International Airport (EYW) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

EYW to MDW Flight Duration and Schedule

Nonstop flight time from EYW to MDW ranges from 3 hours 2 minutes. The route covers a distance of 1,239 miles (1,994 km). There are approximately 1 weekly flights outbound and 1 return, totaling 2 flights per week in both directions.

Connecting Options and Alternatives

60 one-stop connections are available, with the fastest taking approximately 3 hours via STL. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Miami (MIA), Miami (OPF) and Fort Myers (RSW).