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$750+ Cheap flights from Midway (MDW) to Portsmouth, England

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LHR
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Midway to Portsmouth

Keep the following information in mind while searching for Midway to Portsmouth flight deals. Data was last updated September 16, 2025.

Round-trip from

$750
(Delta)

Popular in

June

Cheapest in

February

Average price

$659
From Chicago Midway to Portsmouth
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($208 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Midway to Portsmouth

Cheapest flights from Midway to Portsmouth
Explore the most affordable flight options available from Midway to Portsmouth. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:32 pmMDW - SOU
2 stops17h 28mDelta
Wed 12/108:40 amSOU - MDW
2 stops15h 38mDelta
Deal found 9/14$750
This Netflights deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Netflights is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amMDW - SOU
2 stops21h 20mKLM
Wed 11/58:40 amSOU - MDW
2 stops19h 34mKLM
Deal found 9/14$766
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:14 pmMDW - SOU
2 stops12h 56mDelta
Wed 11/268:40 amSOU - MDW
2 stops15h 38mDelta
Deal found 9/15$826
This KLM deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:00 amMDW - SOU
2 stops15h 45mKLM
Tue 9/305:35 pmSOU - MDW
2 stops30h 00mKLM
Deal found 9/13$1,626
This KLM deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:30 pmMDW - SOU
2 stops16h 30mKLM
Thu 10/25:35 pmSOU - MDW
2 stops31h 00mKLM
Deal found 9/16$1,916
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/299:20 amMDW - SOU
3 stops25h 00mMultiple Airlines
Thu 10/211:25 amSOU - MDW
3 stops27h 14mMultiple Airlines
Deal found 9/16$2,556

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Portsmouth 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 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Portsmouth that are best for you.

Fly from

Midway

Fly to

Portsmouth

Route

Depart

Return

Price

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 12/2

5:32 pm-5:00 pm

2 stops17h 28m

Southampton Eastleigh

Wed 12/10

8:40 am-6:18 pm

2 stops15h 38m

$750

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 12/2

5:32 pm-5:00 pm

2 stops17h 28m

Southampton Eastleigh

Mon 12/8

6:05 pm-6:18 pm

2 stops30h 13m

$750

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 12/2

5:32 pm-5:00 pm

2 stops17h 28m

Southampton Eastleigh

Tue 12/9

8:40 am-6:00 pm

2 stops15h 20m

$750

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 10/29

6:00 am-8:20 am

2 stops21h 20m

Southampton Eastleigh

Wed 11/5

8:40 am-10:14 pm

2 stops19h 34m

$766

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 11/17

1:14 pm-8:10 am

2 stops12h 56m

Southampton Eastleigh

Tue 11/25

8:40 am-6:18 pm

2 stops15h 38m

$826

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 11/18

1:14 pm-8:10 am

2 stops12h 56m

Southampton Eastleigh

Wed 11/26

8:40 am-6:18 pm

2 stops15h 38m

$826

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 11/18

1:14 pm-8:10 am

2 stops12h 56m

Southampton Eastleigh

Tue 11/25

8:40 am-6:18 pm

2 stops15h 38m

$826

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 11/17

1:14 pm-8:10 am

2 stops12h 56m

Southampton Eastleigh

Wed 11/26

8:40 am-6:18 pm

2 stops15h 38m

$826

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 2/25

9:30 am-5:25 pm

2 stops25h 55m

Southampton Eastleigh

Sun 3/1

5:45 pm-6:34 pm

2 stops30h 49m

$848

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 9/27

11:00 am-8:45 am

2 stops15h 45m

Southampton Eastleigh

Tue 9/30

5:35 pm-5:35 pm

2 stops30h 00m

$1,626

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Best time to book a flight from Midway to Portsmouth

Have a flexible travel schedule? Discover the best time to fly to Portsmouth from Midway with our price prediction graph.
Estimated round-trip 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 Chicago Midway Airport to Portsmouth

What is the cheapest time of day to fly from MDW to P0R?

Find hourly flight availability from Midway to Portsmouth. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chicago Midway Airport to Portsmouth, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Midway to Portsmouth. 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 Chicago Midway Airport to Portsmouth?

    Airlines like Delta and KLM fly from Chicago Midway Airport to Portsmouth in about 17h 28m. The time it takes to get you to your destination can typically vary by up to 3h 52m. There are 3924 mi between Chicago Midway Airport and Portsmouth. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Portsmouth 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 Chicago Midway Airport to Portsmouth?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portsmouth (average of $661). Flying from Chicago Midway Airport to Portsmouth in June is currently the most expensive (average of $1,097). 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 Midway to Portsmouth

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

Discover the top airline that operate flights from Midway to Portsmouth. 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 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$536Average$980FlexibilityNo cancel feeOn-timeN/A

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