Cheap Flight Tickets from Chicago (MDW) to Portland (PWM), Starting at $371

Good to Know: Cheapest and Fastest MDW - PWM Flights

Useful information for finding best airline tickets from Chicago Midway International to Portland International Jetport on your next trip.

Cheapest Round Trip Flight

$371

WN Southwest Airlines • 1 stop • 10h 30m

Sep 04 – Sep 07

The cheapest round trip flight from Chicago to Portland (MDW-PWM-MDW) is currently $371

🔍 Search Flights

Cheapest Direct Flight

$371

WN Southwest Airlines • nonstop • 3h 45m

Sep 04

The cheapest nonstop flight from Chicago to Portland (MDW-PWM) is currently $371

🔍 Search Flights

Fastest Flight

3h 45m

The fastest nonstop flight from Chicago to Portland (MDW-PWM) takes 3h 45m

Top Airlines Flying from Chicago to Portland

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Chicago (MDW) to Portland (PWM)

Compare and book low fare round-trip air tickets from Chicago to Portland. Ideal for travelers with confirmed return itineraries.

Sep 04 - Sep 07, Economy
WN
Chicago → Portland
10h 30m
5:55 AM - 1:25 PM • 1 stop
WN
Chicago → Portland
3h 50m
7:40 AM - 9:10 AM • nonstop
$371
Southwest Airlines
Sep 04 - Sep 07, Economy
WN
Chicago → Portland
3h 45m
6:10 PM - 9:35 PM • nonstop
WN
Chicago → Portland
16h 50m
10:30 AM - 7:40 PM • 2 stops
$371
Southwest Airlines
Sep 04 - Sep 07, Economy
WN
Chicago → Portland
10h 30m
5:55 AM - 1:25 PM • 1 stop
WN
Chicago → Portland
7h 15m
5:55 AM - 9:30 AM • 1 stop
$371
Southwest Airlines
Sep 04 - Sep 07, Economy
WN
Chicago → Portland
5h 55m
7:30 AM - 12:25 PM • 1 stop
WN
Chicago → Portland
3h 50m
7:40 AM - 9:10 AM • nonstop
$371
Southwest Airlines
Sep 04 - Sep 07, Economy
WN
Chicago → Portland
9h 15m
8:05 AM - 3:00 PM • 2 stops
WN
Chicago → Portland
7h 15m
10:30 AM - 2:05 PM • 1 stop
$371
Southwest Airlines
Sep 04 - Sep 07, Economy
WN
Chicago → Portland
9h 5m
8:15 AM - 3:00 PM • 2 stops
WN
Chicago → Portland
7h 15m
5:55 AM - 9:30 AM • 1 stop
$371
Southwest Airlines

Fly from Chicago to Portland with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Portland? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Portland Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to PWM?
The most popular airline flying from Chicago to Portland are
Can I fly from MDW to PWM non-stop?
Yes, you can fly MDW to PWM non-stop on
Which airlines fly nonstop between Chicago and Portland?
The non-stop flights between Chicago and Portland are .
What’s the earliest departure time from MDW to PWM Airport?
The earliest flight leaves MDW at 5:55 am and lands in PWM - Portland International Jetport
What are the airports in Portland?
PWM
Can I make changes to my Chicago to Portland flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to PWM?
Read the fare rules of the Chicago to Portland air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Portland?
operate flights between Chicago and Portland
How long does a flight from Chicago to Portland take?
It takes approximately 2 hour to fly non-stop from MDW to PWM, which is 895.38 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Portland (PWM) ?
In the past couple of days, the cheapest tickets to PWM from MDW were found on WN : USD 371
Do I need a passport to fly between MDW and PWM?
No
What’s the latest departure time from MDW to PWM ?
The last flight leaves MDW at 6:10 pm

Chicago (MDW) to Portland (PWM): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Portland International Jetport , Portland, US
Distance 895 miles

More Flight Options for Chicago (MDW) and Portland (PWM)

Why Fareleaders for MDW to PWM Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Portland flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to PWM flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Portland flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Portland (PWM)
Terms and Conditions*