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Portsmouth

$1,380+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LHR
mar 7 — mar 141
sob. 3/7
sob. 3/14
1 adult, Economy
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Cheap 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 Luty 5, 2026.

This Delta deal was found by Cheapflights users on 2/4. 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.
sob. 2/1411:45 am
MDW
-
SOU
2 stops23h 30m
Delta
śr. 3/188:50 am
SOU
-
MDW
2 stops18h 41m
Delta
Deal found 2/4$1,380
This KLM deal was found by Cheapflights users on 2/4. 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.
ndz. 3/297:20 pm
MDW
-
SOU
2 stops15h 30m
KLM
wt. 4/149:05 am
SOU
-
MDW
2 stops15h 31m
KLM
Deal found 2/4$1,414
This Delta deal was found by Cheapflights users on 2/4. 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.
pt. 5/19:31 am
MDW
-
SOU
2 stops17h 14m
Delta
pt. 5/159:05 am
SOU
-
MDW
2 stops18h 04m
Delta
Deal found 2/4$2,165
This KLM deal was found by Cheapflights users on 2/4. 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.
ndz. 3/2212:47 pm
MDW
-
SOU
2 stops14h 33m
KLM
ndz. 3/299:15 am
SOU
-
MDW
2 stops15h 25m
KLM
Deal found 2/4$4,094
This KLM deal was found by Cheapflights users on 2/4. 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.
pt. 5/17:16 pm
MDW
-
SOU
2 stops15h 34m
KLM
pt. 5/159:05 am
SOU
-
MDW
2 stops14h 51m
KLM
Deal found 2/4$6,424

Find flight deals from Midway to Portsmouth

Keep the following information in mind while searching for Midway to Portsmouth flight deals. Data was last updated Luty 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,414
(KLM)

Popular in

June

Cheapest in

April

Average price

$658
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
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($202 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 February 2026
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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 Luty 5, 2026.
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

ndz. 3/29

7:20 pm-4:50 pm

2 stops15h 30m

Southampton Eastleigh

wt. 4/14

9:05 am-6:36 pm

2 stops15h 31m

$1,414

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

pt. 5/1

9:31 am-8:45 am

2 stops17h 14m

Southampton Eastleigh

pt. 5/15

9:05 am-9:09 pm

2 stops18h 04m

$2,165

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

ndz. 3/22

12:47 pm-8:20 am

2 stops14h 33m

Southampton Eastleigh

ndz. 3/29

9:15 am-6:40 pm

2 stops15h 25m

$4,094

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

pt. 5/1

7:16 pm-4:50 pm

2 stops15h 34m

Southampton Eastleigh

pt. 5/15

9:05 am-5:56 pm

2 stops14h 51m

$6,424

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

wt. 6/23

9:20 am-8:35 am

2 stops17h 15m

$4,527

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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
No data available for this route at this time. Please check back soon.

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 KLM and Delta fly from Chicago Midway Airport to Portsmouth in about 15h 30m. The time it takes to get you to your destination can typically vary by up to 1h 44m. 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.

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