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Cheap flights from Portsmouth to Chicago Midway Airport from £706

LHR — MDW
21 Sep — 28 Sep1
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

Thu 1/1009:05 -
2 stops15h 14m
Thu 8/1013:27 -
2 stops13h 08m
Deal found 17/8£706
Sat 5/909:15 -
2 stops19h 21m
Wed 9/909:59 -
2 stops16h 36m
Deal found 20/8£761
Sat 3/1017:20 -
2 stops31h 13m
Sat 10/1013:27 -
2 stops13h 18m
Deal found 19/8£770
Fri 2/1009:05 -
2 stops15h 14m
Fri 9/1013:27 -
2 stops13h 18m
Deal found 18/8£908
Mon 5/1009:05 -
2 stops19h 39m
Mon 12/1012:27 -
2 stops14h 08m
Deal found 21/8£1,693

Find flight deals from Portsmouth to Midway

Round-trip from

£706

Popular in

July

Cheapest in

February

Average price

£699
KLM
  • KLM
  • 1/10-8/10
  • 4 total stops
  • 28h 22m total
  • Portsmouth to Chicago
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Highest demand for flights based on searches. 16% potential increase in price (£82 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
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Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
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
Fastest return journey

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Thu 1/10

09:05-18:19

2 stops15h 14m

Chicago Midway

Thu 8/10

13:27-08:35

2 stops13h 08m

£706

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Sat 5/9

09:15-22:36

2 stops19h 21m

Chicago Midway

Wed 9/9

09:59-08:35

2 stops16h 36m

£761

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Sat 3/10

17:20-18:33

2 stops31h 13m

Chicago Midway

Sat 10/10

13:27-08:45

2 stops13h 18m

£770

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Fri 2/10

09:05-18:19

2 stops15h 14m

Chicago Midway

Fri 9/10

13:27-08:45

2 stops13h 18m

£908

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Mon 5/10

09:05-22:44

2 stops19h 39m

Chicago Midway

Mon 12/10

12:27-08:35

2 stops14h 08m

£1,693

Flights are sorted by cheapest return flights first.

Deals found on 17/8

Sorted by cheapest first

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

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

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

    For as low as £706, KLM can have you in Chicago Midway Airport from Portsmouth in 15h 14m. 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

Top airline flying from Portsmouth to Midway

AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£421Average£676FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

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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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