Cheap Flights from Chicago to Portsmouth

Compare Chicago to Portsmouth flight deals

Find the cheapest month or even day of the year to fly to Portsmouth

Book the best Portsmouth fare with no extra fees

Flight deals from Chicago to Portsmouth

Looking for a cheap last-minute deal or the best return flight from Chicago to Portsmouth? Find the lowest prices on one-way and return tickets right here.

Portsmouth.94 € per passenger.Departing Fri, 15 Aug.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Fri, 15 Aug, arriving in Portsmouth.Price includes taxes and charges.From 94 €, select.

Portsmouth.115 € per passenger.Departing Sun, 12 Oct.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun, 12 Oct, arriving in Portsmouth.Price includes taxes and charges.From 115 €, select.

Find the cheapest month to fly from Chicago to Portsmouth

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Portsmouth flights are currently cheapest in August.

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Chicago to Portsmouth: Alternative routes

Compare routes to Portsmouth below. You may find an airport to fly into that's cheaper, faster, or easier.

Chicago to Portsmouth: Flight information

The things to know before you go.

Cheapest flight found	94 €
Cheapest month to fly	August

Finding cheap flights from Chicago to Portsmouth: Frequently asked questions

How many flights are there a week from Chicago to Portsmouth?

As of April 2025, there are no flights flying from Chicago to Portsmouth.

When is the cheapest time to fly from Chicago to Portsmouth?

The cheapest month to fly from Chicago to Portsmouth is usually April 2025.

Can I get a direct flight from Chicago to Portsmouth Airport?

No airlines currently offer direct flights between Chicago and Portsmouth Airport. Most routes have one or more stops.

How can I find the best flight deal to Portsmouth?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Portsmouth but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Portsmouth?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Portsmouth is around 40 days in advance, so don’t leave your flight to the last minute.

How to find cheap flights to Portsmouth from Chicago

Looking for cheap tickets from Chicago to Portsmouth? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago to Portsmouth. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to Portsmouth from Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
Flex your dates to find the best Chicago-Portsmouth ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Portsmouth from Chicago.
Set up a Price Alert. You can easily track the fare of your cheap Chicago-Portsmouth flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between Chicago and Portsmouth? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
Find the cheapest Business class flights from Chicago and Portsmouth. We scour the internet for the best Business, Premium Economy and First Class flight fares to Portsmouth, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Chicago to Portsmouth flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

Combine your flight to Portsmouth from Chicago with hotels and car hire

Once you've secured your cheap flight ticket from Chicago to Portsmouth, discover the best prices and exclusive rates for hotels in Portsmouth or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.