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

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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.$300 per passenger.Departing Wed, 11 Mar, returning Sat, 14 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Wed, 11 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 14 Mar, arriving in Portland.Price includes taxes and charges.From $300, select.

Chicago.$319 per passenger.Departing Sat, 28 Feb, returning Sat, 7 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sat, 28 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Mar, arriving in Portland.Price includes taxes and charges.From $319, select.

Chicago.$328 per passenger.Departing Wed, 6 May, returning Wed, 13 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Wed, 6 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 13 May, arriving in Portland.Price includes taxes and charges.From $328, select.

Chicago.$342 per passenger.Departing Sun, 5 Apr, returning Tue, 7 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sun, 5 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 7 Apr, arriving in Portland.Price includes taxes and charges.From $342, select.

Chicago.$391 per passenger.Departing Fri, 11 Sep, returning Sat, 26 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Fri, 11 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 26 Sep, arriving in Portland.Price includes taxes and charges.From $391, select.

Chicago.$426 per passenger.Departing Wed, 15 Jul, returning Mon, 20 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Wed, 15 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 20 Jul, arriving in Portland.Price includes taxes and charges.From $426, select.

Chicago.$427 per passenger.Departing Sat, 28 Feb, returning Sat, 28 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sat, 28 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 28 Feb, arriving in Portland.Price includes taxes and charges.From $427, select.

Chicago.$445 per passenger.Departing Thu, 27 Aug, returning Sun, 30 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Thu, 27 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 30 Aug, arriving in Portland.Price includes taxes and charges.From $445, 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 March.

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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	$300
Cheapest month to fly	March
Average flight time	3 hrs, 55 mins
Most popular airline	Southwest Airlines
Average flights per week	15

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

How much are return flights from Portland to Chicago Midway?

The best price we found for a return flight from Portland to Chicago Midway is $300. 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.

How long does it take to fly from Portland to Chicago Midway?

3 hours and 55 minutes is the average flight time from Portland to Chicago Midway.

Which airlines fly direct from Portland to Chicago Midway?

Southwest Airlines flies direct from Portland to Chicago Midway.

How many flights are there a week from Portland to Chicago Midway?

As of February 2026, there are 15 flights per week flying from Portland to Chicago Midway.

When is the cheapest time to fly from Portland to Chicago Midway?

The cheapest month to fly from Portland to Chicago Midway is usually March.

Which upcoming date is cheapest to fly from Portland Airport to Chicago Midway Airport on?

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 Wednesday, 11 March 2026.

Can I get a direct flight from Portland Airport to Chicago Midway Airport?

Yes – the average flight time is 3 hours and 55 minutes.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Portland Airport to Chicago Midway with?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

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

Take a direct flight from Portland International Airport to Chicago Midway International Airport and you'll be in the air for an average of 3 hours 55 minutes.
Chicago is two hours ahead of Portland and is in the UTC-5 timezone.
Each week, there are ten Portland International Airport to Chicago Midway International Airport flights. If you prefer to get going early, opt for the 05:00 Southwest Airlines flight. If you're eager to make the most of your time before you fly, the last departure is at 18:50 with Southwest Airlines.
To ensure you get on your PDX to MDW flight, leave plenty of time to check in and drop off your luggage. Turning up two hours before international departures and one hour before domestic flights is the general travel rule.
During popular months such as July, it's best to get to the airport earlier than usual. Arrive two hours before a domestic departure and four hours ahead for an international flight when you fly during a high season in general.
Southwest Airlines offers direct flights from Portland International Airport to Chicago Midway International Airport. Book with this popular carrier, then get ready to see the sights in Chicago — and maybe even more of United States if time allows.
Most travellers choose to fly with Southwest Airlines on this route.
Southwest Airlines is the most punctual carrier offering PDX to MDW flights. A reliable 93.44% of its services on this route land on time.
We make it a cinch to book a flight with a stopover. To see your options for tickets from Portland International Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, choose a flight with a stop long enough to visit your chosen city. Worthwhile stopovers between PDX and MDW include:
- Denver International Airport
- Minneapolis-St. Paul International Airport
- Salt Lake City International Airport

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

$136 is currently the lowest price for a one-way Portland International Airport to Chicago Midway International Airport flight. A return flight starts at $300. These fares can change depending on demand and availability.
Book six months before your departure date. After crunching the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from PDX to MDW.
Schedule your trip for May. That's the cheapest month for flights from Portland International Airport to Chicago Midway International Airport. If you're flexible with your travel dates, try out the 'Whole month' tool to see the lowest airfare across each month.
There's no need to check every day to find out if fares have dropped when you set up a Price Alert. We'll send you an update as soon as there's a change in price on cheap flights from PDX to MDW.
Pick your ideal departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from Portland International Airport to Chicago Midway International Airport.

Handy information about Portland International Airport (PDX)

PDX is located at 7000 NE Airport Way.
Portland International Airport gets high marks for its on-time performance. 83.65% of flights that take off from PDX reach their destination on time.
To reach Portland International Airport from central Portland, it'll take around 20 minutes if you're going by car. Of course, this depends on traffic. It's approximately 19 kilometres from the airport to the city centre.
The journey when using public transport will take about 45 minutes.
Get your break off to a leisurely start by staying near PDX. Whether you have an early flight from Portland International Airport to Chicago Midway International Airport or just don't want to be rushed, these hotels are ideal:

Arriving at Chicago Midway International Airport (MDW)

If you have a late Portland International Airport to Chicago Midway International Airport flight, nothing beats the convenience of staying near the terminal. Grab your luggage from the carousel and then be showered and resting not long after at one of these options near MDW:
Go wherever you want, whenever you want with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and chase adventure across Chicago and beyond.
Reserving your vehicle from Chicago Midway International Airport around four weeks in advance increases your chances of getting a good deal.

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

MDW is located at 5700 South Cicero.
Chicago Midway International Airport to central Chicago has a drive time of around 20 minutes. It's approximately 19 kilometres away.
It typically takes 45 minutes if you're travelling on public transport.

When to fly to Chicago Midway International Airport (MDW)

July is the most popular month for flights from Portland International Airport to Chicago Midway International Airport. To steer clear of the crowds, head to Chicago in May.
Book your flight from Portland International Airport to Chicago Midway International Airport for July if you want to go to Chicago during its warmest month. Expect temperatures of between 15ºC and 29ºC.
If you like travelling in cooler conditions, search for a cheap ticket from PDX to MDW in January. Average temperatures are between -12ºC and 3ºC then.

Explore more of United States

You've done Chicago, now it's time to discover other parts of United States. Journey about 451 kilometres south-east to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, your itinerary will be busy.
If there's time to check out another major destination in United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.