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Cheap flights from Portsmouth to Chicago Midway Airport from £987

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — MDW
6 Jul — 13 Jul1
1 adult

Cheap flight deals from Portsmouth to Midway

Keep the following information in mind while searching for Portsmouth to Midway flight deals. Data was last updated 1 July 2025.

Round-trip from

£987

Popular in

August

Cheapest in

February

Average price

£640
KLM
  • KLM
  • 4/8-8/9
  • 4 total stops
  • 29h 02m total
  • Portsmouth to Chicago
Highest demand for flights based on searches. 12% potential increase in price (£52 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Average for round-trip flights in July 2025

Find flight deals from Portsmouth to Midway

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 1 July 2025.

Mon 4/809:20SOU - MDW
2 stops15h 20mKLM
Mon 8/913:08MDW - SOU
2 stops13h 42mKLM
Deal found 30/6£987

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 1 July 2025.
Use the filters below to find and compare flights from Portsmouth to Chicago Midway Airport that are best for you.

Fly from

Portsmouth

Fly to

Midway

Route

Depart

Return

Price

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 4/8

09:20-18:40

2 stops15h 20m

Chicago Midway

Mon 8/9

13:08-08:50

2 stops13h 42m

£987

Flights are sorted by cheapest return flights first.

Deals found on 30/6

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

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

Find hourly flight availability from Portsmouth to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 1 July 2025.

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 1 July 2025.
Check out reviews from past customers who have flown with KLM from Portsmouth to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

7.8

Crew

8.4

Boarding

7.8

Comfort

7.7

Food

7.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

Overall

7.8

Crew

8.4

Boarding

7.8

Comfort

7.7

Food

7.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

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.
  • 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.

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 1 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£414Average£620FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

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Can Cheapflights find flights from Portsmouth to Midway with no change fees?

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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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