Which airlines fly from Chicago to Portland?

This route is served by 1 airlines: Southwest Airlines.

Are there direct flights from Chicago to Portland?

Yes, there are direct flights on this route. Check the calendar above — prices for direct flights are highlighted.

Cheap flights Chicago — Portland | Prices from 203 $

Q: How long is the flight from Chicago to Portland?

Approximate flight time — 2 h 11 min. This is an average for a direct flight. With connections, the time may be longer.

Q: What is the distance from Chicago to Portland?

The straight-line distance — 1 425 km. This is the "as-the-crow-flies" distance; the actual route may be longer.

Q: How much do flights from Chicago to Portland cost?

The minimum price over 6 months — from 203 $ on 14.12.2026. Prices depend on the season, day of the week and how far in advance you book.

Q: What is the time difference between Chicago and Portland?

The time difference — +1 h. Keep this in mind when planning your flight and connections.

Q: When is the best time to buy tickets Chicago — Portland?

Optimal — 1–3 months before departure. The cheapest days — Tuesday, Wednesday, Saturday. Check the calendar above — it shows the best dates.

Route characteristics

Distance

1 425 km

Flight time

2 h 11 min

Time difference

+1 h

Minimum price

from 203 $ (14.12.2026)

Departure airports

6 pcs.

Arrival airports

1 pcs.

Airlines on the route

1 pcs.

Who flies this route 1 pcs.

Southwest Airlines

Low-cost 1 flight

Where to buy tickets 1 pcs.

Biletix

1 ticket

Airports

From — Chicago

CGX Merrill C Meigs
DPA DuPage Airport
MDW Chicago Midway International Airport
ORD O'Hare International Airport
PWK Chicago Executive Airport
RFD Chicago Rockford International Airport

To — Portland

PWM Portland International Jetport

Frequently asked questions about the route Chicago — Portland

How long is the flight from Chicago to Portland?

Approximate flight time — 2 h 11 min. This is an average for a direct flight. With connections, the time may be longer. You will see the exact time when searching for tickets.

What is the distance from Chicago to Portland?

The straight-line distance — 1 425 km. This is the "as-the-crow-flies" distance; the actual route may be longer.

How much do flights from Chicago to Portland cost?

The minimum price over 6 months — from 203 $ on 14.12.2026. Prices depend on the season, day of the week and how far in advance you book. Usually cheaper 1–3 months before departure.

What is the time difference?

The difference — +1 h. Keep this in mind when planning your flight and connections.

From which airports does Chicago operate flights?

From Chicago: CGX (Merrill C Meigs), DPA (DuPage Airport), MDW (Chicago Midway International Airport), ORD (O'Hare International Airport), PWK (Chicago Executive Airport), RFD (Chicago Rockford International Airport). Choose the most convenient airport.

To which airports in Portland do flights arrive?

To Portland: PWM (Portland International Jetport). Check which airport your flight arrives at.

Which airlines fly this route?

This route is served by 1 airline: Southwest Airlines.

When is the best time to buy tickets?

Optimal — 1–3 months before departure. The cheapest days — Tuesday, Wednesday, Saturday. Check the calendar above — it shows the best dates.

How do I book tickets?

Choose a date, passengers and click "Find tickets" — a search will open comparing prices from 800+ airlines. Booking is made directly with the airline or agency.

About the route Chicago — Portland

Flights Chicago — Portland is a popular route. The straight-line distance is 1 425 km. Flight time 2 h 11 min. Time difference +1 h.

From Chicago (CHI) flights depart from 6 airports. To Portland (PWM) — one arrival airport.

1 airline operate on this route: Southwest Airlines. Compare prices, baggage allowance and departure times.

The minimum price for the next 6 months — from 203 $ (14.12.2026). The cheapest dates are highlighted in the calendar above.

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