Owensboro to Chicago (OWB–MDW) — Airlines, Schedules & Connections

OWB Airport Page →
airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 3 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 3 hubs
CLT Charlotte 5h 50m LF → WN Charlotte (CLT) to Chicago flights
HOU Houston ~6h 6m → WN Houston (HOU) to Chicago flights
DFW Dallas-Fort Worth ~6h 17m → F9Y4 Dallas-Fort Worth (DFW) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Owensboro to Chicago
Connecting service available through multiple hubs.

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

Also explore OWB Routes MDW Routes OWB Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Owensboro flights
Connections

Connection Landscape

1-stop and 2-stop options for OWB to MDW.
1-STOP
One-Stop Connections
3
Hubs
~5h
Fastest
~6h
Longest
CLT ~5h 50m HOU ~6h 6m DFW ~6h 17m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
158
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
OWB → MDW
67%
Moderate delays possible. Allow buffer time.
Arriving
67%
Return
MDW → OWB
73%
Moderate delays possible. Allow buffer time.
Departing
73%
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 Owensboro

Nearby airports with service to Chicago Midway International Airport.
Metric OWB→MDW EVV→MDW SDF→MDW
Distance from OWB – 29 mi 83 mi
Nonstop airlines – 2 7
Weekly flights – 1 24
Evansville (EVV) to Chicago flights · Louisville (SDF) to Chicago flights · Marion (MWA) to Chicago flights
Airports within 200 miles of OWB with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Chicago is 0 hours the same as Owensboro.
OWB: CDT · MDW: CDT

When it's 6:00 PM in Owensboro, it's 6:00 PM in Chicago.
Facts

OWB–MDW Quick Facts

Key statistics for the Owensboro to Chicago route.
Route details
Time difference0 hours
Airlines (nonstop)0
1-stop connectionsAvailable
Origin: OWB
Full nameOwensboro Daviess County Airport
IATA / ICAOOWB / KOWB
TimezoneAmerica/Chicago
Passengers/yr0.0M
Elevation407 ft / 124 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 OWB to MDW flights.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Charlotte Douglas.
Yes, return flights from MDW to OWB are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include EVV, SDF and MWA. 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 Charlotte Douglas. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Evansville (EVV), Louisville (SDF) and Marion (MWA).