Cheap flights from Chicago to Portland from £98
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore flight deals to Portland
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by departure date
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
How much do flights to Portland cost?
Getting from Portland airport to the city center
Fastest options: MAX Light Rail and taxi/ride-hailing. Best value: TriMet MAX Red Line.
Transport Option | Typical time | Typical cost | Frequency | Best for |
|---|---|---|---|---|
38-45 min | $2.50-$2.80 (adult fare; day pass available) | every 15 min (traffic dependent) | budget travelers | |
45-60 min | $2.50-$2.80 (adult fare; transfers included) | every 15–30 min (traffic dependent) | east side destinations | |
20-40 min | $35-$50 (metered; varies by traffic) | on-demand 24/7 (traffic dependent) | door-to-door convenience | |
20-40 min | $25-$45 (surge pricing may apply) | on-demand 24/7 (traffic dependent) | flexible pickup | |
20-40 min | $50-$90 (pre-booked; fixed rate) | by reservation (traffic dependent) | groups or luggage | |
20-40 min | $40-$100 (per day; varies by provider) | on-demand (traffic dependent) | exploring Oregon |
Notes:
- Prices in USD; table created in 2025 and subject to change.
- MAX Red Line runs directly from the airport terminal to downtown Portland with no transfers required.
- Taxis and ride-hailing pickups are located on the lower level of the terminal.
- We recommend checking official transport websites for your travel planning.
Updated: December 2025
Key info about flying to Portland
Weekly direct flights
Discover the top airlines offering direct flights from Chicago to Portland in the next month. You’ll find the number of daily direct flights per airline in the chart.
| Airline | Mon 09.02 | Tue 10.02 | Wed 11.02 | Thu 12.02 | Fri 13.02 | Sat 14.02 | Sun 15.02 |
|---|---|---|---|---|---|---|---|
| 3 | 2 | 2 | 3 | 3 | 3 | 3 | |
| 1 | 1 | --- | 1 | 1 | 1 | 1 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 25 total | Daily flights: 3.57 average | Most flights: Monday 3 flights |
| Airline | Mon 16.02 | Tue 17.02 | Wed 18.02 | Thu 19.02 | Fri 20.02 | Sat 21.02 | Sun 22.02 |
|---|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 3 | 3 | 3 | 3 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| --- | --- | 1 | 1 | 1 | 1 | 1 | |
| Weekly flights: 30 total | Daily flights: 4.29 average | Most flights: Wednesday 3 flights |
| Airline | Mon 23.02 | Tue 24.02 | Wed 25.02 | Thu 26.02 | Fri 27.02 | Sat 28.02 | Sun 01.03 |
|---|---|---|---|---|---|---|---|
| 2 | --- | 3 | 3 | 3 | --- | 3 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| 1 | --- | 1 | 1 | --- | --- | --- | |
| Weekly flights: 24 total | Daily flights: 3.43 average | Most flights: Wednesday 3 flights |
| Airline | Mon 02.03 | Tue 03.03 | Wed 04.03 | Thu 05.03 | Fri 06.03 | Sat 07.03 | Sun 08.03 |
|---|---|---|---|---|---|---|---|
| 1 | 3 | 3 | 3 | 3 | 3 | 3 | |
| --- | 1 | 1 | 1 | 1 | 1 | 1 | |
| 1 | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 26 total | Daily flights: 3.71 average | Most flights: Tuesday 3 flights |
Check-in for a flight from Chicago to Portland
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| United Airlines | UAL | UA | No |
| Hawaiian Airlines | HAL | HA | No |
| Alaska Airlines | ASA | AS | No |
| Volaris | VOI | Y4 | No |
| VivaAerobus | VIV | VB | No |
Online check-in is not available for these airlines.
Weather in Portland
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | 8°C | 2°C |
| February | 8°C | 2°C |
| March | 11°C | 3°C |
| April | 14°C | 5°C |
| May | 19°C | 8°C |
| June | 23°C | 11°C |
| July | 28°C | 13°C |
| August | 28°C | 15°C |
| September | 24°C | 12°C |
| October | 17°C | 8°C |
| November | 10°C | 4°C |
| December | 7°C | 2°C |
14 day forecast
Portland travel tips
Visit Powell's City of Books in Portland, the largest independent bookstore in the world
In search of a new interesting book, visit Powell's City of Books at 1005 W Burnside Street in Portland, the largest independent bookstore in the world! You will definitely find something good in one of 9 rooms with 3,500 sections and nearly a million books. By the way, prices are also very affordable; there is a large collection of second-hand books.
Explore the underground life of Portland
It's time to explore the Shanghai Tunnels if you know everything about ordinary life in Portland. The unique tour will lead you through the underground catacombs of the late 19th and early 20th centuries. Nobody knows what it was used for, but the hidden trapdoors and holding cells will prompt you.
Use e-scooters to explore Portland's parks
When you go to any park in Portland, make your walk even more exciting with e-scooters. The bright-orange Nike Biketown rental offers good e-scooters. They have stations in every park and cost not so much ($0.10 per minute).
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.
Explore alternative trips
Flights from Chicago
Flights to Portland
Popular routes
Airports near Chicago
Airports near Portland
Download our app