Flight tickets from Chicago to Portland

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Flight deals from Chicago to Portland

Looking for a cheap last-minute deal or the best return flight from Chicago to Portland Airport? If you want to travel next month, return fares start from ₹ 16,268. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Portland

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Portland flights are currently cheapest in September.

Direct flights from Chicago to Portland

Chicago to Portland: Alternative routes

Compare routes from Chicago to Portland below. You may find an airport to fly into that's cheaper, faster, or easier than Portland.

Chicago to Portland: Flight information

The things to know before you go.
Cheapest flight found₹ 8,145
Cheapest month to flySeptember
Average flight time2 hrs, 25 mins
Most popular airlineAmerican Airlines
Average flights per week106

Finding cheap flights from Chicago to Portland: Frequently asked questions

The best price we found for a return flight from Chicago to Portland is ₹ 16,268. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 25 minutes is the average flight time from Chicago to Portland.
American Airlines, United and Republic Airways fly direct from Chicago to Portland.
As of April 2026, there are 106 flights per week flying from Chicago to Portland.
The cheapest month to fly from Chicago to Portland is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Portland Airport on Tuesday, 12 May 2026.
Yes – the average flight time is 2 hours and 25 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Portland but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Portland is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Portland is United .

Travelling from Chicago to Portland International Jetport Airport (PWM): What you need to know

  • The first chapter of your trip begins at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to Portland International Jetport Airport (PWM) setting off from either of these.

  • Around 2 hours 30 minutes is the typical travel time on a direct Chicago to Portland International Jetport Airport flight.

  • The timezone in Portland is UTC-4, which is one hour ahead of Chicago. Portland International Jetport Airport is located in Portland.

  • The most popular route is from O'Hare International Airport (ORD) to Portland International Jetport Airport (PWM), with 23 direct weekly services. If you'd rather get moving right away, the earliest flight from ORD to PWM is the 7:10am United Airlines service. If a later flight fits your day better, the final departure is at 7:10pm with American Airlines.

  • To ensure you get on your flight from Chicago to PWM, leave enough time to navigate the airport and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general rule.

  • In high season, expect extended wait times and be there earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international journeys.

Airports in Chicago

O'Hare International Airport (ORD)

  • Get to your destination in one go from O'Hare International Airport (ORD). Nonstop flights from Chicago to Portland International Jetport Airport (PWM) operate from here.

  • United Airlines is a well-known airline that operates direct flights from Chicago to Portland International Jetport Airport jetting out of ORD.

  • United Airlines is the airline most travellers choose for flights from ORD to PWM.

  • The top on-time carrier on this route is United Airlines. Its services land as planned 77.48% of the time.

  • Located around 40 kilometres from the centre of Chicago, ORD can be reached in about 35 minutes by car, depending on traffic. The journey on public transport takes roughly 55 minutes.

  • Want a leisurely start to your break? Stay near O'Hare International Airport. Whether you're catching an early flight from Chicago to Portland International Jetport Airport or want to avoid feeling rushed, these hotels are the answer:

  • Of the departures from O'Hare International Airport, 74.85% land on schedule at their destination.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Looking to fly out of Chicago Midway International Airport (MDW)? Direct Chicago to Portland International Jetport Airport (PWM) flight tickets are available from this popular hub.

  • Southwest Airlines offers direct flights from Chicago to PWM leaving from MDW. Book your favourite window (or aisle) seat and arrive at your destination in a single hop.

  • On the MDW to PWM route, Southwest Airlines is the top airline in terms of bookings.

  • Using public transport, you can travel from central Chicago to MDW in about 45 minutes. The airport is roughly 19 kilometres away, and getting there by car takes approximately 20 minutes.

  • Got a crack-of-dawn departure? Think about staying at one of these hotels near Chicago Midway International Airport the day before your Chicago to PWM flight:

  • Chicago Midway International Airport has an on-time performance of 77.88%. This figure gives an insight into how frequently flights that leave from this airport arrive on schedule.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kilometres from central Chicago. The drive from the city centre to the airport takes about 1 hour 25 minutes. If you're thinking about using public transport, expect a journey of around 4 hours 15 minutes.

  • Make catching an early Chicago to Portland International Jetport Airport flight one of the easiest parts of your trip. Stay at one of these accommodation options close to Chicago Rockford International Airport and get to your gate feeling relaxed and unhurried:

  • Flights departing from RFD make it to their destination on schedule 76.19% of the time.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Portland International Jetport Airport (PWM)

Getting from Portland International Jetport Airport (PWM) to central Portland

  • Portland International Jetport Airport is around 5 kilometres from central Portland. How long it takes to get to the centre by cab or car hire depends on the time of day. Do a little research before you go.

  • Travelling on public transport takes around 40 minutes.

How to find the cheapest flights from Chicago to Portland International Jetport Airport (PWM)

  • The lowest price we've found for a one-way ticket from Chicago to Portland International Jetport Airport is ₹ 8,145. For a return flight on this route, the best price is ₹ 16,268. Depending on the availability when you book, these fares can change.

  • Don't leave everything to the last minute. You're more likely to find cheap flights from Chicago to PWM if you book early. Airlines often have some excellent early bird discounts.

  • The 'Whole month' search tool will show you the cheapest Chicago to Portland International Jetport Airport tickets throughout the month. It's an easy way to snap up a bargain if your trip dates are flexible.

  • There's no need to check back in every day to find out if prices have dropped when you set up a Price Alert. We'll let you know when a better deal is available on flight tickets from Chicago to PWM.

  • Filters make it easier to find a bargain for your flight from Chicago to Portland International Jetport Airport. Choose the departure times, carriers and stops that work for you. Then sort the results by 'Cheapest' to find the best price quickly.

The best time to fly from Chicago to Portland International Jetport Airport (PWM)

  • Picture the kind of break you want when deciding when to fly. April is the quietest month to visit Portland. August is when most people book flights from Chicago to Portland International Jetport Airport (PWM), which may be perfect if you're chasing more action.

  • Book a Chicago to PWM flight ticket departing in July if you want to visit the city during its warmest month. You can expect temperatures in Portland to range from 14ºC to 25ºC.

  • January sees temperatures of between -10ºC and 3ºC. Search for cheap tickets from Chicago to Portland International Jetport Airport around that time if you like cooler conditions.

More about Portland

Explore more of the United States

  • Boston is just one of the many cities in the United States waiting to be explored once you've seen the sights of Portland. Around 153 kilometres away to the south-west, well-known attractions include Museum of Fine Arts Boston, Freedom Trail and Quincy Market.

  • Around 193 kilometres south-west of Portland, Worcester is another favourite stop in the United States. Experience major highlights starting with Worcester Art Museum, Redemption Rock Brewing and Union Station.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.