Oshkosh to Chicago (OSH–MDW) — Airlines, Schedules & Connections

OSH Airport Page →
157 mi airlines charter/private
On-time Some delays Frequent delays
Flight Schedule Charter / private Verified 1mo 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 More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Oshkosh to Chicago
Flown by charter / private operators — no scheduled airline service.
157 mi 0h 29m nonstop

OSH–MDW has no scheduled airline service; it is flown by charter / private operators.

Also explore Browse available seat maps OSH Routes MDW Routes OSH Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Oshkosh flights
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
OSH → MDW
76%
Generally reliable. Most flights run on time.
Arriving
76%
Return
MDW → OSH
62%
Moderate delays possible. Allow buffer time.
Departing
62%
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 Oshkosh

Nearby airports with service to Chicago Midway International Airport.
Metric OSH→MDW ATW→MDW GRB→MDW
Distance from OSH – 19 mi 40 mi
Nonstop airlines – 2 2
Weekly flights – – 1
Flight time 0h 29m 1h 3m 0h 41m
Appleton (ATW) to Chicago flights · Green Bay (GRB) to Chicago flights · Madison (MSN) to Chicago flights
Airports within 200 miles of OSH 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 Oshkosh.
OSH: CDT · MDW: CDT

When it's 6:00 PM in Oshkosh, it's 6:00 PM in Chicago.
Distance & Flight Time
157 mi / 253 km
Nonstop flight time is approximately 0h 29m gate to gate.
Facts

OSH–MDW Quick Facts

Key statistics for the Oshkosh to Chicago route.
Route details
Distance157 mi / 253 km
Flight time0h 29m
Time difference0 hours
Airlines (nonstop)Charter / private
Origin: OSH
Full nameWittman Regional Airport
IATA / ICAOOSH / KOSH
TimezoneAmerica/Chicago
Elevation808 ft / 246 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 OSH to MDW flights.
Nonstop flights from Wittman Regional Airport to Chicago Midway International Airport take about 0h 29m gate to gate. The route covers 157 miles.
Yes, return flights from MDW to OSH are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ATW, GRB and MSN. 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 OSH to MDW

Wittman Regional Airport (OSH) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

OSH to MDW Flight Duration and Schedule

Nonstop flight time from OSH to MDW is about 0 hours 29 minutes gate to gate. The route covers a distance of 157 miles (253 km).

Connecting Options and Alternatives

Nearby alternative airports include Appleton (ATW), Green Bay (GRB) and Madison (MSN).