PWM to MDW (Portland to Chicago) Flights

Last Minute Flights from PWM to MDW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
PWMChicagoMay 2 to May 4$369
*Prices include taxes and fees

Cheapest PWM to MDW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
PWMChicagoMay 10 to May 16$210
PWMChicagoAugust 28 to August 31$223
PWMChicagoSeptember 25 to September 28$229
PWMChicagoJune 7 to June 10$244
*Prices include taxes and fees
PWM to MDW Flight Details
Origin airport
Portland Intl. Jetport
Origin airport IATA code
PWM
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
892 mi

Frequently asked questions

What airlines fly direct from Portland Intl. Jetport Airport (PWM) to MDW?
Unfortunately, there aren’t any airlines that fly straight from Portland Intl. Jetport to MDW. If you want to reach Chicago, search for a flight with one or more stops.
How many flights are there from PWM to MDW?
Around 2 flights are available daily from Portland, ME (PWM-Portland Intl. Jetport) to Chicago, IL (MDW-Midway Intl.). Buckle up because your plane to Chicago is ready to jet off.
How long does it take to fly from Portland, ME (PWM-Portland Intl. Jetport) to Chicago, IL (MDW-Midway Intl.)?
This flight from Portland, ME (PWM-Portland Intl. Jetport) to Chicago, IL (MDW-Midway Intl.) will take roughly 4 hours and 40 minutes. Use the opportunity to dive into the novel that’s been lying on your bookshelf for a while or just enjoy a snooze.
What is the flight distance from Portland, ME (PWM-Portland Intl. Jetport) to Chicago, IL (MDW-Midway Intl.)?
Portland, ME (PWM-Portland Intl. Jetport) to Chicago, IL (MDW-Midway Intl.) is a short-haul flight of 890 miles (1,450 1). You’ll have barely enough time to relax in your seat before touching down in Chicago.
How many morning flights are there from PWM to MDW?
Buckle up and travel from PWM to MDW on one of the 17 morning flights each week. Delta Air Lines (DL) offers 14 weekly flights leaving before midday. 5:00AM is the first departure time available with this carrier.
How many afternoon flights are there from PWM to MDW?
Jet off on one of the 2 afternoon and evening flights from PWM to MDW per week. Frontier Airlines (F9) has 1 weekly departures from midday. The first leaves the ground at 12:56PM, so you’ll have enough time to make it to the check-in counter.
What is the earliest departure time out of Portland to Chicago?
5:00AM is the earliest flight from PWM, arriving at MDW at 5:18PM. Save precious time in the morning by having your bags zipped up and ready to be bundled into your ride.
What is the latest departure time out of Portland to Chicago?
From PWM, the last flight sets out at 4:30PM and arrives at 1:00PM at MDW. If you’re not a big fan of early mornings, this flight has your name on it.
What is the average price from Portland to Chicago?
Round-trip tickets from PWM to MDW begin from around $210. Great fares don’t last forever, so get set to click “book” when the price is right. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Portland to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Portland to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from PWM to MDW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Portland to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.