Skyscanner home

297 € Cheap Flights from Portland to Chicago Midway

Compare Portland to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Portland to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Portland Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 305 €. Find the lowest prices on one-way and return tickets right here.
Chicago.297 € per passenger.Departing Tue, 20 Oct, returning Thu, 22 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Tue, 20 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 22 Oct, arriving in Portland.Price includes taxes and charges.From 297 €, select.
Chicago.303 € per passenger.Departing Tue, 8 Sep, returning Tue, 8 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Portland on Tue, 8 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 8 Sep, arriving in Portland.Price includes taxes and charges.From 303 €, select.
Chicago.305 € per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 5 Sep, arriving in Portland.Price includes taxes and charges.From 305 €, select.
Chicago.305 € per passenger.Departing Wed, 18 Nov, returning Thu, 19 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Wed, 18 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 19 Nov, arriving in Portland.Price includes taxes and charges.From 305 €, select.
Chicago.305 € per passenger.Departing Thu, 6 Aug, returning Thu, 13 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Thu, 6 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 13 Aug, arriving in Portland.Price includes taxes and charges.From 305 €, select.
Chicago.305 € per passenger.Departing Sat, 19 Sep, returning Mon, 21 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sat, 19 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 21 Sep, arriving in Portland.Price includes taxes and charges.From 305 €, select.
Chicago.309 € per passenger.Departing Thu, 3 Dec, returning Sun, 6 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Thu, 3 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 6 Dec, arriving in Portland.Price includes taxes and charges.From 309 €, select.
Chicago.310 € per passenger.Departing Tue, 28 Jul, returning Tue, 8 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Tue, 28 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Sep, arriving in Portland.Price includes taxes and charges.From 310 €, select.
Chicago.312 € per passenger.Departing Sat, 25 Jul, returning Tue, 28 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sat, 25 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Jul, arriving in Portland.Price includes taxes and charges.From 312 €, select.
Chicago.313 € per passenger.Departing Sun, 27 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sun, 27 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Portland.Price includes taxes and charges.From 313 €, select.
Chicago.313 € per passenger.Departing Sat, 31 Oct, returning Tue, 3 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sat, 31 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Nov, arriving in Portland.Price includes taxes and charges.From 313 €, select.
Chicago.318 € per passenger.Departing Wed, 22 Jul, returning Mon, 10 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Portland on Wed, 22 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 10 Aug, arriving in Portland.Price includes taxes and charges.From 318 €, select.
Chicago.323 € per passenger.Departing Fri, 31 Jul, returning Mon, 10 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Fri, 31 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 10 Aug, arriving in Portland.Price includes taxes and charges.From 323 €, select.
Chicago.341 € per passenger.Departing Sun, 22 Nov, returning Fri, 4 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sun, 22 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 4 Dec, arriving in Portland.Price includes taxes and charges.From 341 €, select.
Chicago.345 € per passenger.Departing Sat, 2 Jan, returning Mon, 4 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Portland on Sat, 2 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 4 Jan, arriving in Portland.Price includes taxes and charges.From 345 €, select.
Chicago.532 € per passenger.Departing Sat, 19 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Portland on Sat, 19 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 2 Jan, arriving in Portland.Price includes taxes and charges.From 532 €, select.

Find the cheapest month to fly from Portland to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Portland to Chicago Midway flights are currently cheapest in October.
Jul
from 312 €
Aug
from 305 €
Sep
from 303 €
Oct
from 297 €
Nov
from 305 €
Dec
from 309 €
Jan
from 345 €
Feb
Find prices
Mar
Find prices
Apr
Find prices
May
Find prices
Jun
Find prices

Direct flights from Portland to Chicago Midway

Portland to Chicago Midway: Alternative routes

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

Chicago Midway

14km from central Chicago
Closest
from 297 €
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from 218 €
Search flights

Chicago Rockford

127km from central Chicago
from 273 €
Search flights

Portland to Chicago: Flight information

The things to know before you go.
Cheapest flight found297 €
Cheapest month to flyOctober
Average flight time3 hrs, 51 mins
Most popular airlineSouthwest Airlines
Average flights per week15

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

The best price we found for a return flight from Portland to Chicago Midway is 297 €. 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.
3 hours and 51 minutes is the average flight time from Portland to Chicago Midway.
Southwest Airlines flies direct from Portland to Chicago Midway.
As of July 2026, there are 15 flights per week flying from Portland to Chicago Midway.
The cheapest month to fly from Portland to Chicago Midway is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago Midway Airport on Tuesday, 20 October 2026.
Yes – the average flight time is 3 hours and 51 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • The average duration of a direct flight from Portland Airport to Chicago Midway Airport is 3 hours 55 minutes.

  • The timezone in Chicago is UTC-6, which is two hours ahead of Portland.

  • Flights from PDX to MDW start at 05:00 — the earliest with Southwest Airlines. The last departure is at 14:35 with Southwest Airlines. Overall, you can choose from nine weekly Portland Airport to Chicago Midway Airport flights.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Be at the airport with enough time to board your PDX to MDW flight.

  • Flying during a peak month like July? Major public holidays and other high seasons can mean longer queues and delays at security. Play things extra safe and arrive up to four hours before international flights and two hours before domestic departures.

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

  • Most passengers choose to fly with Southwest Airlines on this route.

  • Southwest Airlines tops the rankings as the most punctual carrier for PDX to MDW flights, with 90.23% of its services arriving on schedule.

  • We make it a piece of cake to book a flight with a stopover. To see your options for tickets from Portland Airport to Chicago Midway Airport, deselect 'Direct flights only.' Then, choose a flight with a stop long enough to explore the city of your choice. Popular stopovers between PDX and MDW include:

    • Denver International Airport

    • Minneapolis St Paul Airport

    • Salt Lake City Airport

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

  • The cheapest price we've seen for a one-way Portland Airport to Chicago Midway Airport flight is 143 €. A return ticket is currently 297 €. Depending on the availability when you book, these fares may change.

  • To find cheap tickets from PDX to MDW, book ahead. Airlines tend to offer lower fares when flights are first released.

  • May is the cheapest month for flights from Portland Airport to Chicago Midway Airport. If you want to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • Snapping up cheap flights from PDX to MDW is easy with Price Alerts. Simply set up one of these automatic alerts and we'll let you know as soon as a lower fare pops up.

  • Tailor your flights with filters. Select your preferred departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from Portland Airport to Chicago Midway Airport.

Handy information about Portland Airport (PDX)

  • You'll find PDX at 7000 NE Airport Way.

  • 83% of flights leaving Portland Airport land at their destination on time. Given its solid on-time performance, you're unlikely to be delayed when setting off from PDX.

  • To reach Portland Airport from central Portland, it'll take about 20 minutes by car. This depends on traffic, however. It's approximately 19 kilometres from the airport to the city centre.

  • Taking public transport? Expect a trip time of around 40 minutes.

  • Booked an early flight from Portland Airport to Chicago Midway Airport? Avoid rushing to the airport (and enjoy a little extra shut-eye) by picking one of these stays close to PDX:

Arriving at Chicago Midway Airport (MDW)

  • The last thing you want is a long journey to your hotel if you're getting in late on a Portland Airport to Chicago Midway Airport flight. Reserve one of these accommodation options near MDW instead:

  • Go wherever you want, whenever you want with a Chicago Midway Airport rental car. Book your wheels from Dollar, Hertz or Budget and chase adventure across Chicago and beyond.

  • For the best deal, reserve your vehicle from Chicago Midway Airport around four weeks before travelling.

When to fly to Chicago Midway Airport (MDW)

  • It's time to work out your dates for your flight from Portland Airport to Chicago Midway Airport. July is the busiest month to head to Chicago. If you want a quieter vibe, go in December.

  • Before locking in your flight from Portland Airport to Chicago Midway Airport, think about the kind of weather you like. July is the warmest month in Chicago, with the temperature ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from PDX to MDW sometime around then if you want to travel in cooler conditions.

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another well-known destination in the United States and is around 257 kilometres south-east of Chicago. No journey is complete without a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan the rest of your trip from Portland to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.