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Cheap flights from Portsmouth to Chicago Midway Airport from £590

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — MDW
2 Aug — 9 Aug1
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 3 July 2026.

Fri 31/718:05
SOU
-
MDW
2 stops34h 10m
Delta
Thu 6/812:46
MDW
-
SOU
2 stops13h 59m
Delta
Deal found 30/6£997
Sat 4/709:15
SOU
-
MDW
2 stops14h 39m
Delta
Mon 6/719:16
MDW
-
SOU
2 stops16h 19m
Delta
Deal found 30/6£1,224
Tue 11/809:15
SOU
-
MDW
2 stops14h 46m
KLM
Tue 25/810:54
MDW
-
SOU
2 stops15h 51m
KLM
Deal found 2/7£1,353
Wed 1/709:05
SOU
-
MDW
2 stops15h 13m
Virgin Atlantic
Sun 5/718:58
MDW
-
SOU
2 stops31h 47m
Virgin Atlantic
Deal found 30/6£1,381
Wed 5/809:15
SOU
-
MDW
2 stops19h 21m
KLM
Wed 12/819:25
MDW
-
SOU
2 stops16h 10m
KLM
Deal found 29/6£1,428
Sat 15/809:15
SOU
-
MDW
2 stops14h 46m
Delta
Sat 22/816:39
MDW
-
SOU
2 stops18h 21m
Delta
Deal found 1/7£1,492
Sun 2/809:15
SOU
-
MDW
2 stops15h 03m
KLM
Sun 9/813:25
MDW
-
SOU
2 stops13h 20m
KLM
Deal found 1/7£2,114

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 3 July 2026.

Round-trip from

£707

One-way from

£590

Popular in

July

Cheapest in

February

Average price

£702
Delta
  • Delta
  • 16/9-21/9
  • 4 total stops
  • 30h 53m total
  • Portsmouth to Chicago
Search Deals
6/8
  • 6/8
  • 3 total stops
  • 28h 33m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (£80 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
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 3 July 2026.
Use the filters below to find and compare flights from Portsmouth to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 31/7

18:05-22:15

2 stops34h 10m

Chicago Midway

Thu 6/8

12:46-08:45

2 stops13h 59m

£997

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Tue 11/8

09:15-18:01

2 stops14h 46m

Chicago Midway

Tue 25/8

10:54-08:45

2 stops15h 51m

£1,353

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 5/8

09:15-22:36

2 stops19h 21m

Chicago Midway

Wed 12/8

19:25-17:35

2 stops16h 10m

£1,428

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sat 15/8

09:15-18:01

2 stops14h 46m

Chicago Midway

Sat 22/8

16:39-17:00

2 stops18h 21m

£1,492
Fastest return journey

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 2/8

09:15-18:18

2 stops15h 03m

Chicago Midway

Sun 9/8

13:25-08:45

2 stops13h 20m

£2,114
Cheapest one-way

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 6/8

20:00-18:33

3 stops28h 33m

£590

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 24/8

09:15-22:36

2 stops19h 21m

£1,423
Fastest single journey

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 23/8

09:15-18:01

2 stops14h 46m

£1,465

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sat 22/8

09:15-18:01

2 stops14h 46m

£1,465

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 21/8

09:15-22:36

2 stops19h 21m

£1,465

Flights are sorted by cheapest return flights first.

Deals found on 2/7

Showing 1-10 of 11 resultsSorted by cheapest first
1
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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
No data available for this route at this time. Please check back soon.

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 £1,353, Delta can have you in Chicago Midway Airport from Portsmouth in 14h 46m. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 3 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£431Average£668FlexibilityNo 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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