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Cheap flights from Portsmouth to Chicago Midway Airport from £759

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 23/3. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — MDW
21 Feb — 28 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Portsmouth to Midway

Enter your travel dates to find the best prices.

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 22 January 2026.

Mon 23/317:40
SOU
-
MDW
2 stops33h 51m
Virgin Atlantic
Sun 29/309:30
MDW
-
SOU
2 stops25h 20m
Virgin Atlantic
Deal found 19/1£759
Sat 7/309:25
SOU
-
MDW
2 stops19h 06m
Virgin Atlantic
Sat 14/318:34
MDW
-
SOU
2 stops32h 46m
Virgin Atlantic
Deal found 21/1£815
Sun 8/309:30
SOU
-
MDW
2 stops18h 01m
Delta
Sun 15/310:45
MDW
-
SOU
2 stops16h 35m
Delta
Deal found 21/1£1,481
Mon 9/217:35
SOU
-
MDW
2 stops34h 47m
Virgin Atlantic
Fri 13/213:49
MDW
-
SOU
2 stops45h 26m
Virgin Atlantic
Deal found 20/1£2,438

Find flight deals from Portsmouth to Midway

Keep the following information in mind while searching for Portsmouth to Midway flight deals. Data was last updated 22 January 2026.

Round-trip from

£759

Popular in

July

Cheapest in

February

Average price

£465
Virgin Atlantic
  • Virgin Atlantic
  • 23/3-29/3
  • 4 total stops
  • 59h 11m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£65 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 2026
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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 22 January 2026.
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

Mon 23/3

17:40-22:31

2 stops33h 51m

Chicago Midway

Sun 29/3

09:30-16:50

2 stops25h 20m

£759

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sat 7/3

09:25-22:31

2 stops19h 06m

Chicago Midway

Sat 14/3

18:34-08:20

2 stops32h 46m

£815

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 8/3

09:30-22:31

2 stops18h 01m

Chicago Midway

Sun 15/3

10:45-08:20

2 stops16h 35m

£1,481

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 9/2

17:35-22:22

2 stops34h 47m

Chicago Midway

Fri 13/2

13:49-17:15

2 stops45h 26m

£2,438

Flights are sorted by cheapest return flights first.

Deals found on 19/1

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 £418). Flying from Portsmouth to Chicago Midway Airport in December is currently the most expensive (average of £775). 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 £759, Virgin Atlantic can have you in Chicago Midway Airport from Portsmouth in 33h 51m. Portsmouth and Chicago Midway Airport are separated by a distance of 3924 mi.

  • 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 £418). Flying from Portsmouth to Chicago Midway Airport in December is currently the most expensive (average of £775). 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.

See more FAQs

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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 22 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£445Average£561FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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