Cheap Flights from Portsmouth (PSM) to Chicago (MDW)

Popular airlines from Portsmouth, NH (PSM-Portsmouth Intl.) to Chicago Midway Airport (MDW)

Frequently asked questions

How much does a flight from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW)?
The cheapest month to fly from PSM to MDW is , when demand is low. Off-peak months are typically when airlines offer better prices between these airports.
Which airlines fly direct from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW)?
You can't take a direct flight from Portsmouth, NH (PSM-Portsmouth Intl.) to Midway Intl. Airport (MDW). However, you can arrive in Chicago without any layovers by leaving from Logan Intl. Airport (BOS).
What is the cheapest airline that flies from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest PSM to MDW flight.
How many flights per day from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from PSM to MDW?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can change based on various factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW)?
Choose a flight from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from PSM to MDW right before your getaway is typically more expensive. But if you're flexible with your departure times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a PSM to MDW flight and hotel package?
Opting for a PSM to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Portsmouth Intl. Airport (PSM) to Midway Intl. Airport (MDW)?
If you reserved your PSM to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

Travel information

Travel information

Origin airport
Portsmouth Intl.
Destination airport
Midway Intl.
Distance
866 mi

Book with confidence

Book with confidence

Portsmouth to Chicago Flights

The cheapest times to fly from Portsmouth to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portsmouth to Chicago are during the month of . You can find some of the cheapest flights from Portsmouth to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portsmouth to Chicago

Sunday is one of the best days to book for cheap flights from Portsmouth to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portsmouth to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portsmouth to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portsmouth to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portsmouth to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Portsmouth to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.