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$841+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LHR
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
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 November 2, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$841
(Delta)

Popular in

June

Cheapest in

February

Average price

$692
Provider with most accurate pricing for Chicago (CHI)-London (LON) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-London (LON) flights.
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From Chicago Midway to Portsmouth
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Highest demand for flights based on searches. 21% potential increase in price ($201 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 2, 2025.

This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amMDW - SOU
2 stops20h 20mKLM
Wed 12/248:40 amSOU - MDW
2 stops38h 39mKLM
Deal found 11/2$1,313

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 November 2, 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

Wed 2/25

9:34 am-5:25 pm

2 stops25h 51m

Southampton Eastleigh

Sun 3/1

5:45 pm-5:37 pm

2 stops29h 52m

$841

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 12/17

6:00 am-8:20 am

2 stops20h 20m

Southampton Eastleigh

Wed 12/24

8:40 am-5:19 pm

2 stops38h 39m

$1,313

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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 November 2, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Portsmouth in the evening. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the afternoon.

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 20h 20m. The time it takes to get you to your destination can typically vary by up to 5h 31m. 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.

See more FAQs

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Alternative routes for Midway to Portsmouth

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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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$536Average$980FlexibilityNo cancel feeOn-timeN/A

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