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Cheap flights from Portsmouth to Chicago Midway Airport from £649

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — MDW
23 Nov — 30 Nov1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Portsmouth to Midway

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Cheapest flights from Portsmouth to Midway
Explore the most affordable flight options available from Portsmouth to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 October 2025.

Sun 7/1218:05SOU - MDW
2 stops52h 29mVirgin Atlantic
Sun 14/1217:13MDW - SOU
2 stops41h 47mVirgin Atlantic
Deal found 23/10£649

Cheap flight deals from Portsmouth to Midway

Keep the following information in mind while searching for Portsmouth to Midway flight deals. Data was last updated 24 October 2025.

Round-trip from

£649

Popular in

July

Cheapest in

February

Average price

£545
Virgin Atlantic
  • Virgin Atlantic
  • 7/12-14/12
  • 4 total stops
  • 94h 16m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£62 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£9 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Portsmouth to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 24 October 2025.
Use the filters below to find and compare flights from Portsmouth to Chicago Midway Airport that are best for you.

Fly from

Portsmouth

Fly to

Midway

Route

Depart

Return

Price

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 7/12

18:05-16:34

2 stops52h 29m

Chicago Midway

Sun 14/12

17:13-17:00

2 stops41h 47m

£649

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 5/3

18:05-18:08

2 stops30h 03m

Chicago Midway

Mon 9/3

17:59-17:00

2 stops18h 01m

£667

Flights are sorted by cheapest return flights first.

Deals found on 23/10

Best time to book a flight from Portsmouth to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Portsmouth with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portsmouth to Chicago Midway Airport

What is the cheapest month to book a flight from Portsmouth to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Portsmouth to Chicago Midway Airport (average of £417). Flying from Portsmouth to Chicago Midway Airport in July is currently the most expensive (average of £757). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Portsmouth to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portsmouth to Chicago Midway Airport?

    For as low as £667, Virgin Atlantic can have you in Chicago Midway Airport from Portsmouth in 30h 03m. Portsmouth and Chicago Midway Airport are separated by a distance of 3924 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from Portsmouth to Midway that include hotel bookings?

    Yes. In addition to deals on Portsmouth to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Portsmouth to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portsmouth to Midway.

  • Can I find deals for business class flights from Portsmouth to Midway?

    Yes. Cheapflights offers flight deals from Portsmouth to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portsmouth to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Portsmouth to Chicago Midway Airport (average of £417). Flying from Portsmouth to Chicago Midway Airport in July is currently the most expensive (average of £757). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Portsmouth to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Portsmouth to Midway

Discover the top airline that operate flights from Portsmouth to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 24 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£437Average£598FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Portsmouth to Midway?

Deals for Portsmouth to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Portsmouth to Midway?

Millions of users choose and trust Cheapflights to book the best flight deals from Portsmouth to Midway for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Portsmouth to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Portsmouth to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Portsmouth to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Portsmouth today and book when prices fit your budget.

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