Direct (non-stop) flights from Portland (PDX) to Chicago (MDW)
Find comprehensive flight information, schedules, and booking details for direct flights from Portland (PDX), US to Chicago (MDW), US. This popular route is operated by 1 airline, offering multiple daily departures.• Flight Duration: 3h 50m - 4h 00m (average flight time)• Distance: 1756 miles (2825 km) (air miles between airports)• Daily Flights: 1-2 flights (scheduled departures per day)
Portland (PDX)
US
Chicago (MDW)
US
FLIGHT TIME
3h 50m - 4h 00m
FLIGHT DISTANCE
1756 miles (2825 km)
3h 55m - 3h 55m
05:00
05:00
1756 miles (2825 km)
February
1 (Show)
8
Terminal 1 (Chicago (MDW))
Flight Schedule
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Airlines Operating This Route
Click any airline to view their specific flight schedules, policies, and route details for this connection. You can also explore flights from Portland (PDX) and flights to Chicago (MDW).
Route Insights
Route Demand
This route operates 8 flights per week, serving moderate demand between Portland (PDX) and Chicago (MDW).
Best Time to Fly
Best Value Period
February typically offers the best value for travelers, with lower average fares compared to peak travel periods.
Price Trends
Price variation throughout the year is significant, with Feb being the most affordable month and prices increasing during peak travel seasons.
Distance & Duration Explained
Route Distance
At 1756 miles (2825 km), this is an ultra-long-haul route between Portland (PDX) and Chicago (MDW), requiring larger aircraft and extended flight times.
Flight Duration
Flight duration averages 3h 50m - 4h 00m, with actual times ranging from 3h 55m - 3h 55m depending on aircraft type, wind conditions, and routing.
Airline Comparison
Available Airlines
Southwest Airlines is the sole operator on this route, providing 1 daily flight between PDX and MDW.
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Best Time to Visit & Travel Planning
Cheapest Day
Cheapest Month
Average Fare
$268
Travel Planning Tips for Portland (PDX) to Chicago (MDW)
- Best Day to Book
Wednesday typically offers the lowest fares for flights from Portland (PDX) to Chicago (MDW). Consider booking on this day for potential savings.
- Best Month to Travel
January is generally the cheapest month to fly from Portland (PDX) to Chicago (MDW). Plan your trip during this month for the best deals.
- Average Flight Price
The average fare for flights from Portland (PDX) to Chicago (MDW) is approximately $268. Prices may vary based on booking time, season, and airline.
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Related Pages
Related Airports
Related Airlines
Frequently Asked Questions
How many flights operate from Portland (PDX) to Chicago (MDW)?
There is 1 direct flight operating from Portland (PDX) to Chicago (MDW). Approximately 1-2 flights daily.
Which airlines operate flights from Portland (PDX) to Chicago (MDW)?
1 airline operates on this route: Southwest Airlines.
How long is the flight from Portland (PDX) to Chicago (MDW)?
The flight duration from Portland (PDX) to Chicago (MDW) is approximately 3h 50m - 4h 00m.
What is the distance from Portland (PDX) to Chicago (MDW)?
The distance from Portland (PDX) to Chicago (MDW) is 1756 miles (2825 km).
What is the flight time range for this route?
Flight times on this route range from 3h 55m - 3h 55m.
What are the earliest and latest flight departure times?
The earliest flight departs at 05:00 and the latest flight departs at 05:00.
What is the cheapest month to fly from Portland (PDX) to Chicago (MDW)?
February is typically the cheapest month to fly on this route.
How many flights operate per week on this route?
Approximately 8 flights operate per week from Portland (PDX) to Chicago (MDW).
What types of aircraft operate on this route?
This route is served by Boeing 737MAX 8 Passenger.
What is the average flight price from Portland (PDX) to Chicago (MDW)?
The average flight price for a round-trip ticket from Portland (PDX) to Chicago (MDW) is approximately $428 USD. Prices can vary based on booking time, season, and airline.
When is the best time to book flights from Portland (PDX) to Chicago (MDW) for the lowest prices?
February is typically the cheapest month to fly from Portland (PDX) to Chicago (MDW). Booking in advance and avoiding peak travel seasons can help you find better deals.
How far is Chicago (MDW) from Portland (PDX)?
The distance from Portland (PDX) to Chicago (MDW) is 1756 miles (2825 km). This is a long-haul flight route.
How long does it take to fly from Portland (PDX) to Chicago (MDW)?
The flight time from Portland (PDX) to Chicago (MDW) is approximately 3h 50m - 4h 00m. Actual flight duration may vary based on weather conditions, aircraft type, and routing.
What city does Chicago (MDW) serve?
Chicago (MDW) serves Chicago, US.