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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 to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.$180 per passenger.Departing Thu, 23 Jan, returning Tue, 28 Jan.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Thu, 23 Jan, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 28 Jan, arriving in Portland.Price includes taxes and charges.From $180, select.
Chicago.$181 per passenger.Departing Thu, 14 Nov, returning Mon, 18 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Thu, 14 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 18 Nov, arriving in Portland.Price includes taxes and charges.From $181, select.
Chicago.$214 per passenger.Departing Tue, 10 Dec, returning Fri, 13 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Tue, 10 Dec, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 13 Dec, arriving in Portland.Price includes taxes and charges.From $214, select.
Chicago.$242 per passenger.Departing Tue, 26 Nov, returning Wed, 4 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Tue, 26 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 4 Dec, arriving in Portland.Price includes taxes and charges.From $242, select.
Chicago.$249 per passenger.Departing Fri, 21 Feb, returning Sun, 23 Feb.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Fri, 21 Feb, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 23 Feb, arriving in Portland.Price includes taxes and charges.From $249, select.
Chicago.$302 per passenger.Departing Mon, 30 Dec, returning Fri, 3 Jan.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Mon, 30 Dec, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 3 Jan, arriving in Portland.Price includes taxes and charges.From $302, select.
Chicago.$414 per passenger.Departing Thu, 31 Oct, returning Thu, 7 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Thu, 31 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 7 Nov, arriving in Portland.Price includes taxes and charges.From $414, select.
Chicago.$427 per passenger.Departing Fri, 10 Jan, returning Tue, 14 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Fri, 10 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 14 Jan, arriving in Portland.Price includes taxes and charges.From $427, 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 January.
Nov
from $182
Dec
from $215
Jan
from $181
Feb
from $250
Mar
from $724
Apr
Find prices
May
from $808
Jun
from $1,241
Jul
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Aug
from $925
Sep
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Oct
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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.

Portland to Chicago: Flight information

The things to know before you go.
Cheapest flight found$181
Cheapest month to flyJanuary
Average flight time3 hrs, 57 mins
Most popular airlineSouthwest Airlines
Average flights per week12

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 $181. 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 57 minutes is the average flight time from Portland to Chicago Midway.
Southwest Airlines flies direct from Portland to Chicago Midway.
As of November 2024, there are 12 flights per week flying from Portland to Chicago Midway.
The cheapest month to fly from Portland to Chicago Midway is usually November 2024.
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 Thursday, 23 January 2025.
Yes – the average flight time is 3 hours and 57 minutes.
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, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

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

  • The average time for a direct flight from Portland International Airport to Chicago Midway International Airport is 3 hours 55 minutes. Chicago's timezone is UTC-5, making Chicago 2 hours ahead of Portland.

  • There are 10 flights from Portland International Airport to Chicago Midway International Airport weekly. Get the 05:00 flight if you want to leave as soon as possible. If you're keen to leave later, the latest flight from PDX to MDW departs at 22:50.

  • Longer lines at check-in and security are more likely if you're travelling during high season, so allow some extra breathing room. A good rule for peak periods? Arrive up to four hours early for international flights and at least two hours for domestic departures.

  • If you want a stopover for your flight from Portland International Airport to Chicago Midway International Airport, simply uncheck 'Direct flights only' and check out your options. These are the top stopovers between PDX and MDW:

    • Denver International Airport

    • Salt Lake City International Airport

    • Minneapolis-St. Paul International Airport

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

  • The best price we've found for a one-way ticket from Portland International Airport to Chicago Midway International Airport is $91. The cheapest price for a return flight is $180. Bear in mind that fares may change due to availability when booking.

  • To secure flight tickets from PDX to MDW, book your journey 9 months ahead of your departure date.

  • The cheapest month for tickets from Portland International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to find the lowest prices if you have flexible dates.

  • Log into your online account or use the app to create a Price Alert. We'll get in touch straight away if there's a better deal on this route. It's easy to do, and it'll save you from searching for flight tickets from PDX to MDW every day.

  • Use filters to tailor your flights from Portland International Airport to Chicago Midway International Airport. Enter your preferred arrival and departure times, number of stops and airlines. Alternatively, sort your results by 'Cheapest' to see the best deals.

Handy information about Portland International Airport (PDX)

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 21 minutes to reach the centre driving.

  • If you're travelling by public transport, expect a journey of around 46 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to pick your dates for your flight from Portland International Airport to Chicago Midway International Airport. July is the most popular month to visit Chicago. If you like a more peaceful vibe, go in May.

  • The warmest month in Chicago is July, with the temperature ranging between 15 ºC and 29 ºC. Lock in your flights from Portland International Airport to Chicago Midway International Airport in this month if you like this kind of weather.

  • Look for flight tickets from PDX to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -12 ºC and 3 ºC on average.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • You've booked a cheap ticket to Chicago Midway International Airport — next up is finding a great stay, and maybe even a set of wheels. We've compared prices across hundreds of companies to bring you the top hotels and car rental deals in Chicago.

Plan the rest of your trip from Portland to Chicago

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