Flying from Portland, Or to Chicago can be expensive. Our search helps you compare cheap flights, airfare deals, and flight tickets across airlines and agencies so you can book at the best price.
We scan trusted travel agencies and airline booking systems for the route Portland, Or - Chicago (PDX - CHI). We do not sell tickets or add fees - you choose where to buy.
Airfares vary by date, time, and airport. Use filters to find the best option by departure/arrival time, number of stops, airline or alliance, and booking channel.
If your dates are flexible, check the low-fare calendar to find the cheapest days. Booking round-trip in one order often reduces fees, and prices usually rise as departure approaches.
We also recommend you to look through the prices for return tickets from Chicago to Portland, Or.
Airlines are flying from Portland, Or to Chicago
| Southwest Airlines |
Popular flights from Portland, Or
- Cheap flights from Portland, Or to Honolulufrom 33 308र
- Cheap flights from Portland, Or to Las Vegasfrom 17 026र
- Cheap flights from Portland, Or to Konafrom 36 519र
- Cheap flights from Portland, Or to Sochi (Adler)from 190 115र
- Cheap flights from Portland, Or to Los Angeles, Cafrom 25 910र
- Cheap flights from Portland, Or to Minneapolisfrom 6 644र
- Cheap flights from Portland, Or to Orlando Executivefrom 8 702र
- Cheap flights from Portland, Or to Phuketfrom 129 389र
- Cheap flights from Portland, Or to Tokyofrom 28 146र
- Cheap flights from Portland, Or to Phoenixfrom 3 662र
- Cheap flights from Portland, Or to New Yorkfrom 14 816र
- Cheap flights from Portland, Or to San Francisco, CAfrom 12 849र
- Cheap flights from Portland, Or to Khabarovskfrom 149 103र
- Cheap flights from Portland, Or to Samarafrom 136 869र
- Cheap flights from Portland, Or to Miamifrom 25 906र
- Cheap flights from Portland, Or to Mexico Cityfrom 27 239र
- Cheap flights from Portland, Or to Puerto Vallartafrom 17 323र
- Cheap flights from Portland, Or to Jacksonville, FLfrom 21 144र
- Cheap flights from Portland, Or to Nha Trangfrom 103 765र
- Cheap flights from Portland, Or to Palm Springsfrom 9 928र
- Cheap flights from Portland, Or to Istanbulfrom 36 205र
- Cheap flights from Portland, Or to Bangkokfrom 33 720र
- Cheap flights from Portland, Or to Kauai Islandfrom 14 258र
- Cheap flights from Portland, Or to Taipeifrom 75 809र
- Cheap flights from Portland, Or to Nairobifrom 29 097र
- Cheap flights from Portland, Or to Ontariofrom 25 808र
- Cheap flights from Portland, Or to Parisfrom 31 305र
- Cheap flights from Portland, Or to Washingtonfrom 8 965र
- Cheap flights from Portland, Or to Dublinfrom 26 180र
Frequently asked questions about flights from Portland, Or to Chicago
How long does the flight from Portland, Or to Chicago take?
Flight duration from Portland, Or to Chicago varies by route, airline, and number of stops. Direct flights are faster; connecting flights may take longer. Use our search to compare options and see exact durations for your dates.
Are there direct flights from Portland, Or to Chicago?
Availability of direct flights from Portland, Or to Chicago depends on the route and season. Use our search and filter by "Direct" or "Non-stop" to see only direct options. We compare offers from many airlines and agencies.
Which airlines fly from Portland, Or to Chicago?
Several airlines may operate flights from Portland, Or to Chicago. On this page you can see airlines that serve this route. Our search compares prices across airlines and agencies so you can choose the best offer. We do not sell tickets; you book directly with the airline or agency.
What is the cheapest month to fly from Portland, Or to Chicago?
Prices from Portland, Or to Chicago vary by month and demand. On this page you can see average round-trip prices by month. Use the low-fare calendar and monthly table to find the cheapest dates. Booking in advance and avoiding peak seasons often helps get the best price.