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

PDX Airport Page →
1,747 mi airlines 14/wk
On-time Some delays Frequent delays
Flight Schedule 5 flights Verified 12m ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop
✓
→
WN1162
WN Southwest
738
8:05 AM
PDT
1:54 PM
CDT
3h 49m
—
M T W T F S S
Prices
✓
→
WN3708
WN Southwest
738
11:55 PM
PDT
5:50 AM+1
CDT
3h 55m
—
M T W T F S S
Prices
✓
←
WN1651
WN Southwest
737
10:05 AM
CDT
12:25 PM
PDT
4h 20m
—
M T W T F S S
Prices
✓
←
WN3579
WN Southwest
B38M
10:10 AM
CDT
12:30 PM
PDT
4h 20m
—
M T W T F S S
Prices
✓
←
WN2497
WN Southwest
738
8:50 PM
CDT
11:10 PM
PDT
4h 20m
—
M T W T F S S
Prices

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Portland to Chicago
1 carrier, 14 flights/week nonstop.
1 Airlines 14 Flights/wk 1,747 mi 3h 49m nonstop +2h ahead 101 1-stop hubs

PDX–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,747 miles in approximately 3h 49m. Beyond nonstop, 101 hubs offer 1-stop connections.

Also explore PDX Routes MDW Routes PDX Live Flights MDW Live Flights PDX Delays MDW Delays
Carriers on this route

Airline Landscape

All carriers operating nonstop PDX–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 14 738 3h49-3h55 100% – –
Aircraft on this route
738 Boeing 737-800 – 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, PDX to MDW 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
2
Nonstop flights
14
Outbound / wk
15
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for PDX to MDW.
1-STOP
One-Stop Connections
101
Hubs
~5h
Fastest
~32h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
2,610
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.
Alternatives

Other ways to reach Chicago from Portland

Nearby airports with service to Chicago Midway International Airport.
Metric PDX→MDW EUG→MDW SEA→MDW
Distance from PDX – 106 mi 129 mi
Nonstop airlines 1 1 1
Weekly flights 14 – 15
Flight time 3h 49m 4h 27m 3h 46m
Departure OTP 100% – –
Eugene (EUG) to Chicago flights · Seattle (SEA) to Chicago flights
Airports within 200 miles of PDX with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+2h
Chicago is 2 hours ahead of Portland.
PDX: PDT · MDW: CDT

When it's 6:00 PM in Portland, it's 8:00 PM in Chicago.
Distance & Flight Time
1,747 mi / 2,811 km
Nonstop flight time is approximately 3h 49m to 3h 55m.
Facts

PDX–MDW Quick Facts

Key statistics for the Portland to Chicago route.
Route details
Distance1,747 mi / 2,811 km
Flight time3h 49m to 3h 55m
Time difference+2 hours
Airlines (nonstop)1
Weekly flights14 out / 15 return
1-stop connections101 hubs
Origin: PDX
Full namePortland International Airport
IATA / ICAOPDX / KPDX
TimezoneAmerica/Los_Angeles
Passengers/yr17.3M
Elevation31 ft / 9 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 PDX to MDW flights.
Nonstop flights from Portland International Airport to Chicago Midway International Airport take approximately 3h 49m to 3h 55m. The route covers 1,747 miles.
1 airline operates nonstop service: Southwest Airlines.
There are approximately 14 nonstop flights per week from PDX to MDW. The return direction has about 15 weekly flights.
Yes, 1-stop connections are available through MKE, RIL, APA, BOI, BZN, FNL, BIL, SUS, ATW, MSO, YVR, ROG, CMH, OMA, VNY, JAC, HDN, OKC, TRM, OTH, EUG, STS, SNA, FTW, SBA, PSP, PTK, NEW, RNO, SAT, YEG, SCF, CLD, ICT, CID, TEB, GSO, IAD, IAH, SAV, LGA, HPN, TYS, RDU, FOK, SUA, BUF, LAL, YUL, SSI, SJD, TPA, PIE, JAX, SRQ, FLL, ESN, OPF, MTH, CUN, ORD, DTW, DFW, CLT, OAK, SMF, SEA, SFO, STL, MSY, SAN, AUS, LAS, SJC, GRR, ONT, ABQ, PHX, MSP, DSM, DEN, LAX, ATL, GDL, CVG, PHL, SLC, MCI, DAL, BOS, SDF, BNA, DCA, EWR, BWI, TUS, BUR, ASG, MCO, CMA and MIA. These options provide additional schedule flexibility.
Chicago is 2 hours ahead of Portland.
Yes, return flights from MDW to PDX are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include EUG and SEA. 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 PDX to MDW

Portland International Airport (PDX) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 14 weekly departures, this is a well served route.

PDX to MDW Flight Duration and Schedule

Nonstop flight time from PDX to MDW ranges from 3 hours 49 minutes to 3 hours 55 minutes. The route covers a distance of 1,747 miles (2,811 km). There are approximately 14 weekly flights outbound and 15 return, totaling 29 flights per week in both directions.

Connecting Options and Alternatives

101 one-stop connections are available, with the fastest taking approximately 5 hours via MKE. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Eugene (EUG) and Seattle (SEA).