Chicago to Portland (MDW–PWM) — Airlines, Schedules & Connections

MDW Airport Page →
893 mi airlines charter/private 8/wk
On-time Some delays Frequent delays
Flight Schedule 6 flights Verified 1h ago
Also flown by charter / private operators.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop
✓
→
WN1133
WN Southwest
73H
7:40 AM
CDT
10:55 AM
EDT
2h 15m
44%
M T W T F S S
Prices
✓
→
WN1467
WN Southwest
738
1:00 PM
CDT
4:15 PM
EDT
2h 15m
44%
M T W T F S S
Prices
✓
→
WN4272
WN Southwest
738
6:55 PM
CDT
10:10 PM
EDT
2h 15m
44%
M T W T F S S
Prices
✓
←
WN2464
WN Southwest
73H
6:45 AM
EDT
8:20 AM
CDT
2h 35m
—
M T W T F S S
Prices
✓
←
WN3415
WN Southwest
73H
7:40 AM
EDT
9:15 AM
CDT
2h 35m
—
M T W T F S S
Prices
✓
←
WN3642
WN Southwest
7S7
3:55 PM
EDT
5:40 PM
CDT
2h 45m
—
M T W T F S S
Prices

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
BWI Baltimore 4h 10m UAWN → WN Baltimore (BWI) to Portland flights
LGA New York 4h 21m WN → AADLWS New York (LGA) to Portland flights
DCA Washington 4h 22m WN → AA Washington (DCA) to Portland flights
PHL Philadelphia 4h 26m EJAWN → AAASEJA Philadelphia (PHL) to Portland flights
BNA Nashville 4h 46m WN → WN Nashville (BNA) to Portland flights
CLT Charlotte 5h 8m WN → AA Charlotte (CLT) to Portland flights
CMH Columbus 5h 19m EJAWN → MX Columbus (CMH) to Portland flights
ATL Atlanta 5h 28m AFAMDL → AFAMDL Atlanta (ATL) to Portland flights
DTW Detroit 5h 33m AFDLKE → DLKEWS Detroit (DTW) to Portland flights
PIT Pittsburgh 5h 36m WN → MX Pittsburgh (PIT) to Portland flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Portland
1 carrier, 8 flights/week nonstop.
1 Airlines 893 mi 2h 15m nonstop +1h ahead

MDW–PWM is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 893 miles in approximately 2h 15m. Beyond nonstop, 1-stop connecting options are also available.

Also explore MDW Routes PWM Routes MDW Live Flights PWM Live Flights MDW Delays PWM Delays
All flights from Portland (PWM) Portland to Chicago flights
Carriers on this route

Airline Landscape

All carriers operating nonstop MDW–PWM service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 8 738, 73H 2h15 53% – –
Aircraft on this route
738 Boeing 737-800 – WN
73H Boeing 737-800 (Winglets) – WN
Alliance coverage
Unaffiliated: WN (8 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Schedule

Weekly Schedule Pattern

Nonstop flight frequency by day of week, MDW to PWM direction.
Mon
1
flight
Tue
1
flight
Wed
1
flight
Thu
1
flight
Fri
1
flight
Sat
2
flights
Sun
1
flight
Departure time distribution
12 AM6 AM12 PM6 PM12 AM
Morning departures
Afternoon/evening departures
3
Nonstop flights
8
Outbound / wk
7
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for MDW to PWM.
1-STOP
One-Stop Connections
29
Hubs
~4h
Fastest
~28h
Longest
BWI ~4h 10m LGA ~4h 21m DCA ~4h 22m PHL ~4h 26m IND ~4h 33m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,449
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 → PWM
53%
Frequent delays expected. Consider flexible booking.
Departing
53%
Arriving
28%
Return
PWM → MDW
64%
Moderate delays possible. Allow buffer time.
Departing
64%
Arriving
59%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays → PWM delays →
Alternatives

Other ways to reach Portland from Chicago

Nearby airports with service to Portland International Jetport.
Metric MDW→PWM ORD→PWM
Distance from MDW – 15 mi
Nonstop airlines 1 8
Weekly flights 8 71
Flight time 2h 15m 1h 45m
Departure OTP 53% –
Chicago (ORD) to Portland flights
Airports within 200 miles of MDW with service to Portland International Jetport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago, it's 7:00 PM in Portland.
Distance & Flight Time
893 mi / 1,437 km
Nonstop flight time is approximately 2h 15m gate to gate.
Facts

MDW–PWM Quick Facts

Key statistics for the Chicago to Portland route.
Route details
Distance893 mi / 1,437 km
Flight time2h 15m
Time difference+1 hour
Airlines (nonstop)1
Weekly flights8 out / 7 return
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: PWM
Full namePortland International Jetport
IATA / ICAOPWM / KPWM
TimezoneAmerica/New_York
Passengers/yr2.4M
Elevation76 ft / 23 m
FAQ

Frequently Asked Questions

Common questions about MDW to PWM flights.
Nonstop flights from Chicago Midway International Airport to Portland International Jetport take about 2h 15m gate to gate. The route covers 893 miles.
1 airline operates flights from MDW to PWM: Southwest Airlines.
This route has daily service. Check the schedule above for departure days and times in each direction.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Baltimore/Washington International Thurgood Marshall, LaGuardia and Ronald Reagan Washington National.
Portland is 1 hour ahead of Chicago.
Yes, return flights from PWM to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD. 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 PWM

Chicago Midway International Airport (MDW) and Portland International Jetport (PWM) are connected by nonstop service from Southwest Airlines. With 8 weekly departures, this is a regularly served route.

MDW to PWM Flight Duration and Schedule

Nonstop flight time from MDW to PWM is about 2 hours 15 minutes gate to gate. The route covers a distance of 893 miles (1,437 km). There are approximately 8 weekly flights outbound and 7 return, totaling 15 flights per week in both directions.

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Baltimore/Washington International Thurgood Marshall, LaGuardia and Ronald Reagan Washington National. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).