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Cheap flights from Portsmouth to Chicago Midway Airport from £435

LHR — MDW
18 Oct — 25 Oct1
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 15/1009:29 -
2 stops17h 06m
Deal found 14/9£913
Sat 31/1009:25 -
2 stops18h 08m
Sat 7/1109:29 -
2 stops17h 26m
Deal found 16/9£1,091

Find flight deals from Portsmouth to Midway

Round-trip from

£913

One-way from

£435

Popular in

August

Cheapest in

February

Average price

£609
Delta
  • Delta
  • 1/10-15/10
  • 4 total stops
  • 32h 20m total
  • Portsmouth to Chicago
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1/10-31/12
  • 1/10-31/12
  • 3 total stops
  • 56h 05m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£65 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 September 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.

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Route

Depart

Return

Price

Cheapest return flight

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Wed 30/9

12:35-11:00

3 stops52h 25m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£438

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Thu 1/10

20:00-11:00

2 stops45h 00m

Chicago Midway

Wed 31/12

00:00-07:00

Nonstop0h 00m

£557
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 15/10

09:29-08:35

2 stops17h 06m

£913

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Sat 31/10

09:25-22:33

2 stops18h 08m

Chicago Midway

Sat 7/11

09:29-08:55

2 stops17h 26m

£1,091

Flights are sorted by cheapest return flights first.

Deals found on 18/9

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 £913, Delta 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.

  • 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

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Top airline flying from Portsmouth to Midway

AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£430Average£726FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

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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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