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

EYW Airport Page →
1,239 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 14 1-stop flights Verified 3w ago
Charter / private route. No scheduled airline service — operated by NetJets Aviation, Executive Jet Management.
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
TPA Tampa 4h 38m MX → NJEWN Tampa (TPA) to Chicago flights
TYS Knoxville/Maryville 4h 40m G4 → G4 Knoxville/Maryville (TYS) to Chicago flights
ATL Atlanta 4h 42m AFAMDL → AFAMDL Atlanta (ATL) to Chicago flights
MIA Miami 4h 44m AABAQR → EJAWN Miami (MIA) to Chicago flights
CVG Cincinnati / Covington 4h 55m G4 → WN Cincinnati / Covington (CVG) to Chicago flights
CLT Charlotte 5h 18m AA → WN Charlotte (CLT) to Chicago flights
MCO Orlando 5h 41m MX → WN Orlando (MCO) to Chicago flights
DCA Washington 6h AAAS → WN Washington (DCA) to Chicago flights
PHL Philadelphia 6h 41m AAAS → WN Philadelphia (PHL) to Chicago flights
IND Indianapolis 7h 20m G4 → WN Indianapolis (IND) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Key West to Chicago
Flown by charter / private operators — no scheduled airline service.
1,239 mi 2h 38m nonstop -1h behind

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

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

Connection Landscape

1-stop and 2-stop options for EYW to MDW.
1-STOP
One-Stop Connections
14
Hubs
~4h
Fastest
~22h
Longest
TPA ~4h 38m TYS ~4h 40m ATL ~4h 42m MIA ~4h 44m CVG ~4h 55m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
931
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
EYW → MDW
72%
Moderate delays possible. Allow buffer time.
Arriving
72%
Return
MDW → EYW
63%
Moderate delays possible. Allow buffer time.
Departing
63%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
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 – 13 9
Weekly flights ~1 16 2
Flight time 2h 38m 2h 43m 2h 36m
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 2h 38m gate to gate.
Facts

EYW–MDW Quick Facts

Key statistics for the Key West to Chicago route.
Route details
Distance1,239 mi / 1,994 km
Flight time2h 38m
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out
1-stop connectionsAvailable
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 about 2h 38m gate to gate. The route covers 1,239 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Tampa, McGhee Tyson and Hartsfield Jackson Atlanta.
On a single ticket, yes. Your bags are checked through to MDW and move between planes without you. On two separate tickets you collect your bags at the connecting airport and recheck them, so build in extra layover time.
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 is about 2 hours 38 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 Tampa, McGhee Tyson and Hartsfield Jackson Atlanta. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Miami (MIA), Miami (OPF) and Fort Myers (RSW).