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

MDW Airport Page →
1,747 mi airlines 15/wk
On-time Some delays Frequent delays
Flight Schedule 5 flights Verified 33m ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop
✓
→
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
✓
←
WN1162
WN Southwest
738
5:09 AM
PDT
11:01 AM
CDT
3h 52m
—
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

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
Chicago to Portland
2 carriers, 15 flights/week nonstop.
2 Airlines 15 Flights/wk 1,747 mi 3h 37m nonstop -2h behind 95 1-stop hubs

MDW–PDX is served by 2 airlines with nonstop service. Southwest Airlines and Delta Air Lines lead the route. The flight covers 1,747 miles in approximately 3h 37m. Beyond nonstop, 95 hubs offer 1-stop connections.

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

Airline Landscape

All carriers operating nonstop MDW–PDX service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 14 737, 738, B38M 4h20 100% – –
DL Delta Air Lines 0 – – 100% SkyTeam –
Aircraft on this route
737 Boeing 737-700 – WN
738 Boeing 737-800 – WN
B38M Boeing 737 MAX 8 – WN
Alliance coverage
Unaffiliated: WN (14 flights/wk, 100%)
SkyTeam: DL (0 flights/wk, 0%)
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 PDX 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
3
Nonstop flights
15
Outbound / wk
14
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for MDW to PDX.
1-STOP
One-Stop Connections
95
Hubs
~4h
Fastest
~32h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
2,623
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 Portland from Chicago

Nearby airports with service to Portland International Airport.
Metric MDW→PDX ORD→PDX
Distance from MDW – 15 mi
Nonstop airlines 2 10
Weekly flights 15 193
Flight time 3h 37m 4h 20m
Departure OTP 100% –
Chicago (ORD) to Portland flights
Airports within 200 miles of MDW with service to Portland International Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago, it's 4:00 PM in Portland.
Distance & Flight Time
1,747 mi / 2,811 km
Nonstop flight time is approximately 3h 37m to 4h 20m.
Facts

MDW–PDX Quick Facts

Key statistics for the Chicago to Portland route.
Route details
Distance1,747 mi / 2,811 km
Flight time3h 37m to 4h 20m
Time difference-2 hours
Airlines (nonstop)2
Weekly flights15 out / 14 return
1-stop connections95 hubs
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: PDX
Full namePortland International Airport
IATA / ICAOPDX / KPDX
TimezoneAmerica/Los_Angeles
Passengers/yr17.3M
Elevation31 ft / 9 m
FAQ

Frequently Asked Questions

Common questions about MDW to PDX flights.
Nonstop flights from Chicago Midway International Airport to Portland International Airport take approximately 3h 37m to 4h 20m. The route covers 1,747 miles.
2 airlines operate nonstop service: Delta Air Lines and Southwest Airlines.
There are approximately 15 nonstop flights per week from MDW to PDX. The return direction has about 14 weekly flights.
Yes, 1-stop connections are available through YVR, JAC, FCM, ICT, EGE, ASE, OKC, YWG, BIL, BOI, YEG, MKC, BZN, CMH, BFI, MSN, MSO, APA, PIT, SUN, ELP, LGB, PVU, OTH, VNY, HPN, RNO, SDF, MEM, ORD, TEB, RDU, TRM, STS, SAT, SCF, PDK, UDD, GSO, ISP, AFW, HOU, SNA, SGR, SBA, PSP, FXE, IAD, DSM, IAH, PBI, JFK, SJD, TPA, STL, ABQ, FLL, CUN, CLT, BWI, MCO, DCA, EWR, DTW, ATL, HND, OAK, LAS, PHX, MCI, DEN, GRR, SEA, TUS, SLC, SMF, BOS, AUS, LAX, DFW, DAL, PHL, SFO, SJC, MSP, SAN, CVG, ONT, MIA, BUR, MSY, GDL, BNA, HCR and BXM. These options provide additional schedule flexibility.
Portland is 2 hours behind Chicago.
Yes, return flights from PDX 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 PDX

Chicago Midway International Airport (MDW) and Portland International Airport (PDX) are connected by nonstop service from Delta Air Lines and Southwest Airlines. With 15 weekly departures, this is a well served route.

MDW to PDX Flight Duration and Schedule

Nonstop flight time from MDW to PDX ranges from 3 hours 37 minutes to 4 hours 20 minutes. The route covers a distance of 1,747 miles (2,811 km). There are approximately 15 weekly flights outbound and 14 return, totaling 29 flights per week in both directions.

Connecting Options and Alternatives

95 one-stop connections are available, with the fastest taking approximately 4 hours via YVR. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).