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

MDW Airport Page →
893 mi airlines charter/private 14/wk
On-time Some delays Frequent delays
Flight Schedule 12 flights Verified 36m ago
Also flown by charter / private operators: NetJets Aviation.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop
✓
→
WN2775
Starts Oct 6 Seat map
WN Southwest
7M8 Seat map
7:45 AM
CDT
10:55 AM
EDT
2h 10m
51%
M T W T F S S
Prices
✓
→
WN4720
Starts Oct 3
WN Southwest
73H
4:10 PM
CDT
7:20 PM
EDT
2h 10m
51%
M T W T F S S
Prices
✓
→
WN2398
Starts Oct 1
WN Southwest
73H
6:40 PM
CDT
9:50 PM
EDT
2h 10m
51%
M T W T F S S
Prices
✓
→
WN431
WN Southwest
737
6:45 PM
CDT
9:46 PM
EDT
2h 1m
51%
M T W T F S S
Prices
✓
→
WN300
WN Southwest
7S7
6:50 PM
CDT
10:10 PM
EDT
2h 20m
51%
M T W T F S S
Prices
✓
→
WN2746
Starts Oct 4
WN Southwest
73H
7:50 PM
CDT
11:05 PM
EDT
2h 15m
51%
M T W T F S S
Prices
✓
←
WN2876
Starts Oct 1
WN Southwest
73H
6:30 AM
EDT
8:05 AM
CDT
2h 35m
—
M T W T F S S
Prices
✓
←
WN3550
Starts Oct 4
WN Southwest
73H
7:25 AM
EDT
9:00 AM
CDT
2h 35m
—
M T W T F S S
Prices
✓
←
WN3338
WN Southwest
7S7
7:40 AM
EDT
9:10 AM
CDT
2h 30m
—
M T W T F S S
Prices
✓
←
WN2751
Seat map
WN Southwest
7M8 Seat map
3:45 PM
EDT
5:20 PM
CDT
2h 35m
—
M T W T F S S
Prices
✓
←
WN3557
Starts Oct 3
WN Southwest
73H
4:35 PM
EDT
6:10 PM
CDT
2h 35m
—
M T W T F S S
Prices
✓
←
WN1881
Starts Oct 6
WN Southwest
73H
6:00 PM
EDT
7:35 PM
CDT
2h 35m
—
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 5m WN → WN Baltimore (BWI) to Portland flights
LGA New York 4h 18m WN → AADLWS New York (LGA) to Portland flights
PHL Philadelphia 4h 30m EJAWN → AAASQR Philadelphia (PHL) to Portland flights
PIT Pittsburgh 4h 35m WN → MX Pittsburgh (PIT) to Portland flights
BNA Nashville 4h 40m EJAWN → WN Nashville (BNA) to Portland flights
DCA Washington 4h 44m WN → AA Washington (DCA) to Portland flights
CLT Charlotte 4h 56m LXJWN → AA Charlotte (CLT) to Portland flights
CMH Columbus 5h 2m WN → MX Columbus (CMH) to Portland flights
ATL Atlanta 5h 15m AFAMDL → AFAMDL Atlanta (ATL) to Portland flights
DTW Detroit 5h 24m AFDLKE → DLKEWS Detroit (DTW) to Portland flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Portland
1 carrier, 14 flights/week nonstop.
1 Airlines 893 mi 2h 10m 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 10m. Beyond nonstop, 1-stop connecting options are also available.

Also explore Choose a flight to see its seat map 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 14 737, 73H, 7M8, 7S7 2h01-2h20 100% – –
Aircraft on this route
737 Boeing 737-700 – WN
73H Boeing 737-800 (Winglets) – WN
7M8 Boeing 737 MAX 8 – WN
7S7 Boeing 737 MAX 7 – WN
Alliance coverage
Unaffiliated: WN (14 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
2
flights
Tue
2
flights
Wed
2
flights
Thu
2
flights
Fri
2
flights
Sat
2
flights
Sun
2
flights
Departure time distribution
12 AM6 AM12 PM6 PM12 AM
Morning departures
Afternoon/evening departures
6
Nonstop flights
14
Outbound / wk
14
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for MDW to PWM.
1-STOP
One-Stop Connections
19
Hubs
~4h
Fastest
~19h
Longest
BWI ~4h 5m LGA ~4h 18m PHL ~4h 30m PIT ~4h 35m BNA ~4h 40m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,337
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
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
100%
Return
PWM → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
100%
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 GYY→PWM
Distance from MDW – 15 mi 21 mi
Nonstop airlines 1 9 1
Weekly flights 14 96 –
Flight time 2h 10m 2h 13m 1h 52m
Departure OTP 100% – –
Chicago (ORD) to Portland flights · Gary (GYY) 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 10m 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 10m
Time difference+1 hour
Airlines (nonstop)1
Weekly flights14 out / 14 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 10m 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 Philadelphia.
On a single ticket, yes. Your bags are checked through to PWM 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.
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 and GYY. 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 14 weekly departures, this is a well served route.

MDW to PWM Flight Duration and Schedule

Nonstop flight time from MDW to PWM is about 2 hours 10 minutes gate to gate. The route covers a distance of 893 miles (1,437 km). There are approximately 14 weekly flights outbound and 14 return, totaling 28 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 Philadelphia. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD) and Gary (GYY).