Cheap Flight Tickets from Portland (PDX) to Chicago (MDW), Starting at $210

Good to Know: Cheapest and Fastest PDX - MDW Flights

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

Cheapest Round Trip Flight

$420

WN Southwest Airlines • nonstop • 5h 55m

Aug 31 – Sep 07

The cheapest round trip flight from Portland to Chicago (PDX-MDW-PDX) is currently $420

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Cheapest Direct Flight

$210

WN Southwest Airlines • nonstop • 5h 55m

Aug 27

The cheapest nonstop flight from Portland to Chicago (PDX-MDW) is currently $210

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Fastest Flight

5h 55m

The fastest nonstop flight from Portland to Chicago (PDX-MDW) takes 5h 55m

Top Airlines Flying from Portland to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Aug 31 - Sep 07, Economy
WN
Portland → Chicago
5h 55m
6:15 AM - 12:10 PM • nonstop
WN
Portland → Chicago
13h 20m
9:00 AM - 3:00 PM • 1 stop
$420
Southwest Airlines
Aug 31 - Sep 07, Economy
WN
Portland → Chicago
11h 45m
7:55 PM - 5:00 AM • 1 stop
WN
Portland → Chicago
6h 50m
10:40 AM - 12:50 PM • nonstop
$425
Southwest Airlines
Aug 31 - Sep 07, Economy
WN
Portland → Chicago
12h 10m
5:45 AM - 3:15 PM • 1 stop
WN
Portland → Chicago
6h 50m
10:40 AM - 12:50 PM • nonstop
$425
Southwest Airlines
Aug 31 - Sep 07, Economy
WN
Portland → Chicago
11h 55m
2:05 PM - 11:20 PM • 1 stop
WN
Portland → Chicago
7h
8:50 PM - 11:10 PM • nonstop
$425
Southwest Airlines
Aug 31 - Sep 07, Economy
WN
Portland → Chicago
11h 40m
8:00 AM - 5:00 PM • 1 stop
WN
Portland → Chicago
13h 20m
9:00 AM - 3:00 PM • 1 stop
$425
Southwest Airlines
Aug 31 - Sep 07, Economy
WN
Portland → Chicago
15h 5m
12:40 PM - 11:45 PM • 2 stops
WN
Portland → Chicago
13h 20m
9:00 AM - 3:00 PM • 1 stop
$431
Southwest Airlines

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

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

FAQs on Portland to Chicago Flights

What are the airports in Portland?
PDX
What’s the most popular airline flying from PDX to MDW?
The most popular airline flying from Portland to Chicago are
Can I fly from PDX to MDW non-stop?
Yes, you can fly PDX to MDW non-stop on
Which airlines fly nonstop between Portland and Chicago?
The non-stop flights between Portland and Chicago are .
What’s the earliest departure time from PDX to MDW Airport?
The earliest flight leaves PDX at 5:45 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Portland to Chicago 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 PDX to MDW?
Read the fare rules of the Portland to Chicago 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 Portland and Chicago?
operate flights between Portland and Chicago
How long does a flight from Portland to Chicago take?
It takes approximately 4 hour to fly non-stop from PDX to MDW, which is 1751.25 miles by air.
Which airlines provide the cheapest flights from Portland (PDX) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from PDX were found on WN : USD 431
Do I need a passport to fly between PDX and MDW?
No
What’s the latest departure time from PDX to MDW ?
The last flight leaves PDX at 11:30 pm

Essential Information for Booking Flights from Portland (PDX) - AI Insights

What's the cheapest airline from pdx to mdw?
You can find affordable flights from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) on Southwest Airlines. For a business class ticket, consider booking in advance to secure Low Fares. With 19 days of advance booking, you may be able to snag Budget-friendly airfares for your Round Trip journey.
What's the popular airline to fly from pdx to mdw?
Southwest Airlines offers a budget-friendly option for your round-trip Business class flights from Portland International Airport (PDX) to Chicago Midway International Airport (MDW), with two stops. Booking in advance, 19 days prior to your trip, can help secure Low Fares on this route.
What's the cheapest day of the week to fly from pdx to mdw?
The cheapest day to fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) is Sunday. Flying on Sundays can result in budget-friendly flights, making it a great option for travelers looking to save on airfares. Low fares and savings are often available during this time.
What's the cheapest month to fly from pdx to mdw?
The cheapest month to fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) is September. This is based on historical airfare data, which suggests that September tends to offer lower fares compared to other months. For a business class ticket with priority, lounge access, and flatbed seats, you can expect to pay around the same fare for both legs of your round-trip journey. To secure the best rates, we recommend booking at least 19 days in advance. By flying during off-peak seasons like July, October, December, November, or February, you may be able to find even cheaper flights. Keep an eye on airfare deals and discounts from airlines and online travel agencies to score affordable airfares.
Which airline/airlines fly from pdx to mdw?
United Airlines (UA) and Allegiant Air (G4) operate flights from Portland International Airport (PDX) to Chicago Midway International Airport (MDW). For a round-trip Business class ticket, book at least 19 days in advance for the best savings. You can also consider other airlines like Delta (DL), Volaris (Y4), Southwest Airlines (WN), Frontier Airlines (F9), JetBlue Airways (B6), Alaska Airlines (AS), American Airlines (AA), and Sun Country Airlines (SY) for your travel plans.
What is the cheapest airline to fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)?
Southwest Airlines (WN)
How far in advance should I book my flight for a round trip from PDX to MDW?
It is recommended to book your flight at least 19 days in advance for the best fares.
Can I find affordable flights on your website for July travel?
Yes, you can find affordable flights on our website for July travel.
What are the different types of cabins available on flights from PDX to MDW?
There is a Business (Premium service with priority, lounge, and flatbed seats) cabin option available on this route.
Are there any discounts or promotions available for business class passengers on this route?
Yes, we offer discounts and promotions for business class passengers.

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

Origin Airport Portland International , Portland, US
Destination Airport Chicago Midway International , Chicago, US
Distance 1751 miles

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