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

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Frequently asked questions

Is it cheaper to buy a plane ticket from Portsmouth Intl. Airport (PSM) to Chicago Airport last minute?
Being the spontaneous type is a fabulous way to discover the world, but it's not necessarily the smartest way to land a cheap fare. It's better to book your Portsmouth Intl. Airport at Pease to Midway Airport journey well ahead of time rather than leaving it till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. We recommend saving that spontaneity for when you get to your destination!
What airports do you fly into for Chicago from Portsmouth?
From Portsmouth, you can reach Chicago through Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT). It's wise to check which terminal is the right option for you before you make a decision. If you decide on Midway Intl. Airport (MDW), it's around 14 kilometers southwest of the center of the city. Use the dollars you save when booking your airfare with Expedia to check out the city's top attractions, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from Portsmouth Intl. Airport at Pease to MDW?
It's so easy to make changes to your Portsmouth Intl. Airport at Pease to Midway Airport trip yourself. Just log in to the Expedia Trips portal and tap "change flight." Browse around for new flights and secure the one that works best. You'll see an estimate of applicable flight change fees. You can also head to our Customer Service portal to connect with our Virtual Agent and quickly get answers to your questions.

Travel information

Travel information

Origin airport
Portsmouth Intl.
Destination airport
Midway Intl.
Distance
1385 km

Book with confidence

Book with confidence

Portsmouth to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Portsmouth to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Portsmouth to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Portsmouth to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia