Pittsfield to Chicago (PSF–MDW) — Airlines, Schedules & Connections

PSF Airport Page →
742 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Flight Schedule Charter / private 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 More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Pittsfield to Chicago
Flown by charter / private operators — no scheduled airline service.
742 mi 2h nonstop -1h behind

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

Also explore PSF Routes MDW Routes PSF Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Pittsfield flights
Connections

Connection Landscape

1-stop and 2-stop options for PSF to MDW.
1-STOP
One-Stop Connections
0
Hubs
–
Fastest
–
Longest
Verified with published schedule alignment and minimum connection time.
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
PSF → MDW
67%
Moderate delays possible. Allow buffer time.
Arriving
67%
Return
MDW → PSF
100%
Generally reliable. Most flights run on time.
Departing
100%
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 Pittsfield

Nearby airports with service to Chicago Midway International Airport.
Metric PSF→MDW ALB→MDW BDL→MDW
Distance from PSF – 34 mi 46 mi
Nonstop airlines – 2 3
Weekly flights ~1 21 21
Flight time 2h 2h 10m 1h 54m
Albany (ALB) to Chicago flights · Hartford (BDL) to Chicago flights · Worcester (ORH) to Chicago flights
Airports within 200 miles of PSF 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 Pittsfield.
PSF: EDT · MDW: CDT

When it's 6:00 PM in Pittsfield, it's 5:00 PM in Chicago.
Distance & Flight Time
742 mi / 1,194 km
Nonstop flight time is approximately 2h 0m gate to gate.
Facts

PSF–MDW Quick Facts

Key statistics for the Pittsfield to Chicago route.
Route details
Distance742 mi / 1,194 km
Flight time2h
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out
1-stop connectionsAvailable
Origin: PSF
Full namePittsfield Municipal Airport
IATA / ICAOPSF / KPSF
TimezoneAmerica/New_York
Elevation1,188 ft / 362 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 PSF to MDW flights.
Nonstop flights from Pittsfield Municipal Airport to Chicago Midway International Airport take about 2h gate to gate. The route covers 742 miles.
Yes, 1-stop connections are available, ranked by layover time.
Chicago is 1 hour behind Pittsfield.
Yes, return flights from MDW to PSF are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ALB, BDL and ORH. 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 PSF to MDW

Pittsfield Municipal Airport (PSF) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

PSF to MDW Flight Duration and Schedule

Nonstop flight time from PSF to MDW is about 2 hours gate to gate. The route covers a distance of 742 miles (1,194 km).

Connecting Options and Alternatives

1-stop connecting options are also available. Nearby alternative airports include Albany (ALB), Hartford (BDL) and Worcester (ORH).