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

MDW Airport Page →
1,239 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 22 1-stop flights Verified 1w ago
Charter / private route. No scheduled airline service — operated by charter & private aviation.
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
ATL Atlanta 4h 45m AFAMDL → AFAMDL Atlanta (ATL) to Key West flights
CLT Charlotte 5h 7m WN → AA Charlotte (CLT) to Key West flights
MCO Orlando 5h 22m WN → MX Orlando (MCO) to Key West flights
TPA Tampa 6h 6m WN → MX Tampa (TPA) to Key West flights
DCA Washington 6h 16m WN → AA Washington (DCA) to Key West flights
MIA Miami 8h 17m WN → AAUA Miami (MIA) to Key West flights
PIT Pittsburgh 9h 37m WN → G4 Pittsburgh (PIT) to Key West flights
FLL Fort Lauderdale 9h 42m WN → MTN Fort Lauderdale (FLL) to Key West flights
IND Indianapolis 13h 2m WN → G4 Indianapolis (IND) to Key West flights
RDU Raleigh/Durham 14h 37m WN → MX Raleigh/Durham (RDU) to Key West flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Key West
Flown by charter / private operators — no scheduled airline service.
1,239 mi 2h 43m nonstop +1h ahead

MDW–EYW has no scheduled airline service; it is flown by charter / private operators. 1-stop connecting options are also available.

Also explore MDW Routes EYW Routes MDW Live Flights EYW Live Flights MDW Delays
All flights from Key West (EYW) Key West to Chicago flights
Connections

Connection Landscape

1-stop and 2-stop options for MDW to EYW.
1-STOP
One-Stop Connections
22
Hubs
~4h
Fastest
~24h
Longest
PIE ~4h 40m ATL ~4h 45m SRQ ~4h 58m CLT ~5h 7m AVL ~5h 18m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,094
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
MDW → EYW
40%
Frequent delays expected. Consider flexible booking.
Departing
40%
Return
EYW → MDW
51%
Frequent delays expected. Consider flexible booking.
Arriving
51%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Key West from Chicago

Nearby airports with service to Key West International Airport.
Metric MDW→EYW ORD→EYW SBN→EYW
Distance from MDW – 15 mi 74 mi
Nonstop airlines – 4 1
Weekly flights ~1 21 –
Flight time 2h 43m 3h 24m 1h 43m
Departure OTP 40% – –
Chicago (ORD) to Key West flights · South Bend (SBN) to Key West flights · Milwaukee (MKE) to Key West flights
Airports within 200 miles of MDW with service to Key West International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+1h
Key West is 1 hour ahead of Chicago.
MDW: CDT · EYW: EDT

When it's 6:00 PM in Chicago, it's 7:00 PM in Key West.
Distance & Flight Time
1,239 mi / 1,994 km
Nonstop flight time is approximately 2h 43m gate to gate.
Facts

MDW–EYW Quick Facts

Key statistics for the Chicago to Key West route.
Route details
Distance1,239 mi / 1,994 km
Flight time2h 43m
Time difference+1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out / ~1 return
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: EYW
Full nameKey West International Airport
IATA / ICAOEYW / KEYW
TimezoneAmerica/New_York
Passengers/yr1.5M
Elevation3 ft / 1 m
FAQ

Frequently Asked Questions

Common questions about MDW to EYW flights.
Nonstop flights from Chicago Midway International Airport to Key West International Airport take about 2h 43m gate to gate. The route covers 1,239 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Hartsfield Jackson Atlanta, Charlotte Douglas and Orlando.
Key West is 1 hour ahead of Chicago.
Yes, return flights from EYW to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD, SBN and MKE. 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 EYW

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

MDW to EYW Flight Duration and Schedule

Nonstop flight time from MDW to EYW is about 2 hours 43 minutes gate to gate. The route covers a distance of 1,239 miles (1,994 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Hartsfield Jackson Atlanta, Charlotte Douglas and Orlando. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), South Bend (SBN) and Milwaukee (MKE).