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Cheap Flights from Chicago Midway (MDW) to Portland (PDX)

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Flight deals from Chicago Midway Airport to Portland Airport

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Portland Airport? If you want to travel next month, return fares start from £188. Find the lowest prices on one-way and return tickets right here.
Portland.£188 per passenger.Departing Sat, 18 Apr, returning Sat, 25 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 18 Apr, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Sat, 25 Apr, arriving in Chicago Midway.Price includes taxes and charges.From £188, select.
Portland.£212 per passenger.Departing Wed, 13 May, returning Tue, 19 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 13 May, arriving in Portland.Inbound indirect flight with Southwest Airlines, departs from Portland on Tue, 19 May, arriving in Chicago Midway.Price includes taxes and charges.From £212, select.
Portland.£217 per passenger.Departing Wed, 29 Apr, returning Mon, 4 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Apr, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Mon, 4 May, arriving in Chicago Midway.Price includes taxes and charges.From £217, select.
Portland.£217 per passenger.Departing Wed, 20 May, returning Mon, 25 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 20 May, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Mon, 25 May, arriving in Chicago Midway.Price includes taxes and charges.From £217, select.
Portland.£229 per passenger.Departing Sat, 30 May, returning Tue, 2 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 30 May, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Tue, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
Portland.£229 per passenger.Departing Sat, 15 Aug, returning Tue, 18 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 15 Aug, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Tue, 18 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
Portland.£229 per passenger.Departing Wed, 22 Jul, returning Wed, 5 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 22 Jul, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Wed, 5 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
Portland.£229 per passenger.Departing Tue, 30 Jun, returning Sat, 4 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 30 Jun, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Sat, 4 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
Portland.£229 per passenger.Departing Sat, 20 Jun, returning Sat, 27 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 20 Jun, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Sat, 27 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
Portland.£229 per passenger.Departing Wed, 1 Jul, returning Tue, 7 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 1 Jul, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Tue, 7 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £229, select.
Portland.£246 per passenger.Departing Mon, 14 Sep, returning Thu, 17 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 14 Sep, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Thu, 17 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £246, select.
Portland.£261 per passenger.Departing Fri, 29 Jan, returning Mon, 8 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 29 Jan, arriving in Portland.Inbound indirect flight with Delta, departs from Portland on Mon, 8 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £261, select.
Portland.£275 per passenger.Departing Tue, 29 Sep, returning Sun, 4 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 29 Sep, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Sun, 4 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £275, select.
Portland.£302 per passenger.Departing Thu, 5 Nov, returning Tue, 10 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 5 Nov, arriving in Portland.Inbound indirect flight with Delta, departs from Portland on Tue, 10 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £302, select.
Portland.£430 per passenger.Departing Mon, 23 Mar, returning Thu, 26 Mar.Return flight with Frontier Airlines and Allegiant Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 23 Mar, arriving in Portland.Inbound indirect flight with Allegiant Air, departs from Portland on Thu, 26 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £430, select.
Portland.£471 per passenger.Departing Thu, 26 Mar, returning Mon, 30 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 26 Mar, arriving in Portland.Inbound direct flight with Southwest Airlines departs from Portland on Mon, 30 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £471, select.

Find the cheapest month to fly from Chicago Midway to Portland

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Portland flights are currently cheapest in April.
Mar
from £430
Apr
from £188
May
from £212
Jun
from £229
Jul
from £229
Aug
from £229
Sep
from £246
Oct
Find prices
Nov
from £302
Dec
Find prices
Jan
Find prices
Feb
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Direct flights from Chicago Midway to Portland

Chicago Midway to Portland: Alternative routes

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

Portland

6 miles from central Portland
ClosestCheapest
from £188
Search flights

Salem

45 miles from central Portland
Search flights

Chicago to Portland: Flight information

The things to know before you go.
Cheapest flight found£188
Cheapest month to flyApril
Average flight time4 hrs, 20 mins
Most popular airlineSouthwest Airlines
Average flights per week18

Check out these Portland hotels

Ready to plan your stay? Other travellers rate these Portland hotels for cleanliness, service and location.
Violet Suites PDX
1.34 miles from city centre
£286
Per night
The Ritz-Carlton, Portland
0.16 miles from city centre
£374
Per night
Bluebird Guesthouse
2.65 miles from city centre
£130
Per night
Violet Suites PDX
1.34 miles from city centre
£286
Per night
The Ritz-Carlton, Portland
0.16 miles from city centre
£374
Per night
Bluebird Guesthouse
2.65 miles from city centre
£130
Per night
Explore top-rated hotels

Finding cheap flights from Chicago Midway to Portland: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Portland is £188. 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.
4 hours and 20 minutes is the average flight time from Chicago Midway to Portland.
Southwest Airlines flies direct from Chicago Midway to Portland.
As of March 2026, there are 18 flights per week flying from Chicago Midway to Portland.
The cheapest month to fly from Chicago Midway to Portland is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Portland Airport on Saturday, 18 April 2026.
Yes – the average flight time is 4 hours and 20 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.
Currently, Southwest Airlines offers the cheapest flight tickets to Portland.

Flying from Chicago Midway International Airport (MDW) to Portland International Airport (PDX): what you need to know

  • The average time for a direct flight from Chicago Midway International Airport to Portland International Airport is 4 hours 20 minutes.

  • Portland's timezone is UTC-7, making Portland two hours behind Chicago.

  • Flights from MDW to PDX start at 08:10 — the first with Southwest Airlines. The last service of the day is at 22:50 with Southwest Airlines. In total, you can take your pick of ten weekly Chicago Midway International Airport to Portland International Airport flights.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to board your MDW to PDX flight.

  • During popular months such as July, it's a good idea to get to the airport earlier than normal. Arrive two hours before domestic departures and four hours ahead for an international flight when you travel during a peak period in general.

  • Southwest Airlines offers direct flights from Chicago Midway International Airport to Portland International Airport. Book with this popular airline, then get ready to discover the sights in Portland — and maybe even more of United States if your schedule allows.

  • The airline that serves the most passengers on this route is Southwest Airlines.

  • With a reliable 80.33% of services landing on schedule, Southwest Airlines is the most punctual carrier for MDW to PDX flights.

  • Consider adding a stopover when booking your ticket from Chicago Midway International Airport to Portland International Airport. Just deselect 'Direct flights only' to break up your trip, or even explore someplace new along the way. Check out these options between MDW and PDX:

    • Minneapolis-St. Paul International Airport

    • Denver International Airport

    • Kansas City International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)

  • The cheapest price we've found for a one-way Chicago Midway International Airport to Portland International Airport flight is £94. A return ticket right now is £188. Depending on the availability when you book, these fares may change.

  • To get cheap tickets from MDW to PDX, reserve your journey six months ahead of your planned departure.

  • The cheapest month for flights from Chicago Midway International Airport to Portland International Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have a flexible travel schedule.

  • Snapping up cheap flights from MDW to PDX is a cinch with Price Alerts. Simply create one of these automatic alerts and we'll let you know when a new discounted fare appears.

  • Discover the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Chicago Midway International Airport to Portland International Airport, use the 'Sort by' function. You can also filter results by airline, arrival and departure times, and journey duration.

Handy information about Chicago Midway International Airport (MDW)

  • The address for MDW is 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway International Airport, data shows 77.88% of flights arrive within the expected timeframe.

  • Central Chicago to Chicago Midway International Airport is around 12 miles. Depending on traffic, it'll take about 20 minutes to get there if you're catching a cab, ride-sharing or driving.

  • The trip when using public transport will take about 45 minutes.

  • Taking an early flight from Chicago Midway International Airport to Portland International Airport? Avoid rushing to the airport (and sneak in some extra snooze time) by picking one of these stays close to MDW:

Arriving at Portland International Airport (PDX)

Getting from Portland International Airport (PDX) to central Portland

  • PDX is located at 7000 NE Airport Way.

  • Portland International Airport is approximately 12 miles from the centre of Portland. Driving there takes about 20 minutes.

  • Travelling on public transport will take you roughly 45 minutes.

When to fly to Portland International Airport (PDX)

  • July is the most popular month for flights from Chicago Midway International Airport to Portland International Airport. To escape the crowds, head to Portland in May.

  • The warmest month in Portland is August, with temperatures ranging between 12ºC (54ºF) and 31ºC (88ºF). Lock in your flights from Chicago Midway International Airport to Portland International Airport in this month if this is the type of weather you enjoy.

  • December has average temperatures of between 0ºC (32ºF) and 9ºC (48ºF). Search for cheap tickets from MDW to PDX sometime then if you like travelling in cooler conditions.

Explore more of United States

  • Seattle is just one of the many places in United States waiting to be explored once you've seen Portland. Around 150 miles away to the north, check out popular attractions including Greyhound: Bus Station, LMN Architects and Boeing Radiation Effects Lab.

  • Around 290 miles north-east of Portland, Spokane is another essential stop in United States. No visit is complete without checking out Manito Park, Northwest Museum of Arts & Culture and Spokane Falls.

Plan the rest of your trip from Chicago to Portland

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