Cheap Flights from Chicago Midway IL to Portland OR from $226

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Flight deals from Chicago Midway to Portland

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway Airport to Portland Airport? If you want to travel next month, round-trip fares start from $226. Find the lowest prices on one-way and round-trip tickets right here.

Portland.$226 per passenger.Departing Thu, Aug 27, returning Mon, Aug 31.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Aug 27, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Mon, Aug 31, arriving in Chicago Midway.Price includes taxes and charges.From $226, select.

Portland.$226 per passenger.Departing Thu, Sep 10, returning Mon, Sep 14.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Sep 10, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Mon, Sep 14, arriving in Chicago Midway.Price includes taxes and charges.From $226, select.

Portland.$227 per passenger.Departing Mon, Aug 31, returning Tue, Sep 1.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Aug 31, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Tue, Sep 1, arriving in Chicago Midway.Price includes taxes and charges.From $227, select.

Portland.$227 per passenger.Departing Mon, Sep 28, returning Thu, Oct 1.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Sep 28, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Thu, Oct 1, arriving in Chicago Midway.Price includes taxes and charges.From $227, select.

Portland.$236 per passenger.Departing Mon, Nov 16, returning Tue, Nov 17.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Mon, Nov 16, arriving in Portland.Inbound indirect flight with Southwest Airlines, departing from Portland on Tue, Nov 17, arriving in Chicago Midway.Price includes taxes and charges.From $236, select.

Portland.$236 per passenger.Departing Thu, Oct 15, returning Wed, Oct 21.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Oct 15, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Wed, Oct 21, arriving in Chicago Midway.Price includes taxes and charges.From $236, select.

Portland.$302 per passenger.Departing Wed, Dec 9, returning Wed, Dec 30.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Wed, Dec 9, arriving in Portland.Inbound indirect flight with Southwest Airlines, departing from Portland on Wed, Dec 30, arriving in Chicago Midway.Price includes taxes and charges.From $302, select.

Portland.$340 per passenger.Departing Fri, Nov 6, returning Sun, Nov 8.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Fri, Nov 6, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Sun, Nov 8, arriving in Chicago Midway.Price includes taxes and charges.From $340, select.

Portland.$350 per passenger.Departing Tue, Jul 28, returning Fri, Aug 14.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Jul 28, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Fri, Aug 14, arriving in Chicago Midway.Price includes taxes and charges.From $350, select.

Portland.$357 per passenger.Departing Sat, Oct 31, returning Wed, Nov 11.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Oct 31, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Wed, Nov 11, arriving in Chicago Midway.Price includes taxes and charges.From $357, select.

Portland.$358 per passenger.Departing Wed, Jan 6, returning Sat, Jan 9.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Wed, Jan 6, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Sat, Jan 9, arriving in Chicago Midway.Price includes taxes and charges.From $358, select.

Portland.$358 per passenger.Departing Tue, Feb 2, returning Tue, Feb 16.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Feb 2, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Tue, Feb 16, arriving in Chicago Midway.Price includes taxes and charges.From $358, select.

Portland.$383 per passenger.Departing Tue, Dec 1, returning Fri, Jan 8.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Tue, Dec 1, arriving in Portland.Inbound indirect flight with Southwest Airlines, departing from Portland on Fri, Jan 8, arriving in Chicago Midway.Price includes taxes and charges.From $383, select.

Portland.$386 per passenger.Departing Thu, Dec 10, returning Thu, Dec 17.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Dec 10, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Thu, Dec 17, arriving in Chicago Midway.Price includes taxes and charges.From $386, select.

Portland.$407 per passenger.Departing Sat, Jul 18, returning Tue, Jul 21.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Jul 18, arriving in Portland.Inbound direct flight with Southwest Airlines departing from Portland on Tue, Jul 21, arriving in Chicago Midway.Price includes taxes and charges.From $407, 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 August.

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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

10km from central Portland

ClosestCheapest

from $226

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Chicago to Portland: Flight information

The things to know before you go.

Cheapest flight found	$226
Cheapest month to fly	August
Average flight time	4 hrs, 25 mins
Most popular airline	Southwest Airlines
Average flights per week	18

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

How much are round-trip flights from Chicago Midway to Portland?

The best price we found for a round-trip flight from Chicago Midway to Portland is $226. 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 Chicago Midway to Portland?

4 hours and 25 minutes is the average flight time from Chicago Midway to Portland.

Which airlines fly direct from Chicago Midway to Portland?

Southwest Airlines flies direct from Chicago Midway to Portland.

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

There are 18 flights per week flying from Chicago Midway to Portland, as of July 2026.

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

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

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

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 Thursday, August 27, 2026.

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

Yes – the average flight time is 4 hours and 25 minutes.

How can I find the best flight deal to Portland?

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.

When is the best time to book flights to Portland?

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.

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

Currently, Southwest Airlines offers the cheapest flight tickets to Portland.

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

The average length of a direct flight from Chicago Midway Airport to Portland Airport is 4 hours 20 minutes.
Portland is two hours behind Chicago and follows the UTC-8 timezone.
Flights from MDW to PDX start at 07:45 — the first with Southwest Airlines. The latest departure is at 22:25 with Southwest Airlines. Overall, you can choose from nine weekly Chicago Midway Airport to Portland Airport flights.
Get to the airport on time so you don't miss your MDW to PDX flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.
During popular months such as July, you'll want to get to the airport earlier than normal. Arrive two hours before domestic departures and four hours ahead for an international flight when you fly during a peak period in general.
Southwest Airlines is your gateway to discovering Portland (and perhaps some other exciting parts of the United States!). Browse the direct flights from Chicago Midway Airport to Portland Airport offered by this popular carrier.
Southwest Airlines is the top choice for travelers on this route.
Southwest Airlines is the most punctual carrier that operates MDW to PDX flights, with 69.47% of its services arriving on schedule.
Think about adding a stopover when booking your ticket from Chicago Midway Airport to Portland Airport. Simply uncheck 'Direct flights only' to break up your trip, or perhaps explore a new destination along the way. Check out these options between MDW and PDX:
- Denver International Airport
- Minneapolis St Paul Airport
- Kansas City International Airport

Handy information about Chicago Midway Airport (MDW)

You'll find MDW at 5700 South Cicero.
Of all flights departing from Chicago Midway Airport, 76% land on schedule at their destination.
Chicago Midway Airport is around 16 kilometers from central Chicago. If you're ride-sharing, catching a cab or driving from the center, it'll take you 25 minutes or so to arrive, depending on the traffic.
Expect a journey time of roughly 30 minutes on public transport.
Searching for a convenient hotel close to MDW? If you're boarding an early flight from Chicago Midway Airport to Portland Airport, these accommodation options will have you moments from your departure lounge:

Arriving at Portland Airport (PDX)

The last thing you need is a long journey to your hotel if you're getting in late on a Chicago Midway Airport to Portland Airport flight. Check in to one of these accommodation options near PDX instead:
Travel at your own speed with a Portland Airport rental car. Pick up your wheels from Thrifty, Budget or Hertz and find adventure across Portland and beyond.
To lock in the lowest price, book your ride from Portland Airport around one week before traveling.

When to fly to Portland Airport (PDX)

It's time to pick your trip dates for your flight from Chicago Midway Airport to Portland Airport. July is the busiest month to head to Portland. If you'd like a more laid-back vibe, go in March.
The warmest month in Portland is August, with the temperature ranging between 12ºC (54ºF) and 31ºC (88ºF). Book your flights from Chicago Midway Airport to Portland Airport in this month if this is the type of weather you like.
January has average temperatures of between -2ºC (28ºF) and 10ºC (50ºF). Search for cheap tickets from MDW to PDX sometime around then if you like traveling in cooler conditions.

Explore more of the United States

You've done Portland, now it's time to explore more of the United States. Journey around 241 kilometers north to Seattle to tick off its must-visit sights. From Space Needle to Pike Place Market and Seattle Skyline, you'll have a packed itinerary ahead.
Spokane is another essential stop in the United States and is around 467 kilometers north-east of Portland. No journey is complete without visiting Riverside State Park, Spokane Falls (Upper Falls) and Cathedral of Our Lady of Lourdes.