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$551+ Cheap flights from Midway (MDW) to Southampton (SOU)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SOU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to Southampton

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Southampton (SOU). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$936
(Delta)

One-way from

$551
(Delta)

Popular in

June

Cheapest in

February

Average price

$713
From Chicago Midway to Southampton Eastleigh
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One-way flight from Chicago Midway to Southampton Eastleigh
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Highest demand for flights based on searches. 21% potential increase in price ($203 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Midway to Southampton

Cheapest flights from Midway to Southampton
Explore the most affordable flight options available from Midway to Southampton. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 11/191:00 pmMDW - SOU
2 stops13h 20mDelta
Wed 11/268:40 amSOU - MDW
2 stops15h 27mDelta
Deal found 8/12$936
This KLM deal was found by Cheapflights users on 8/13. 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.
Fri 10/311:08 pmMDW - SOU
2 stops14h 42mKLM
Thu 11/138:50 amSOU - MDW
2 stops15h 17mKLM
Deal found 8/13$1,138
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2310:08 amMDW - SOU
2 stops16h 02mDelta
Mon 1/59:25 amSOU - MDW
2 stops37h 00mDelta
Deal found 8/13$1,162
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:00 amMDW - SOU
2 stops15h 45mDelta
Sat 10/49:20 amSOU - MDW
2 stops15h 15mDelta
Deal found 8/13$1,640
This KLM deal was found by Cheapflights users on 8/12. 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 8/2510:31 amMDW - SOU
2 stops16h 19mKLM
Thu 8/285:35 pmSOU - MDW
2 stops30h 02mKLM
Deal found 8/12$1,916
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 8/279:15 amMDW - SOU
2 stops17h 30mDelta
Sat 8/309:20 amSOU - MDW
2 stops17h 52mDelta
Deal found 8/14$1,967
This Delta deal was found by Cheapflights users on 8/12. 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.
Sat 9/136:15 pmMDW - SOU
2 stops17h 35mDelta
Thu 10/29:20 amSOU - MDW
2 stops18h 16mDelta
Deal found 8/12$2,104
This Delta deal was found by Cheapflights users on 8/12. 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.
Sat 9/137:15 pmMDW - SOU
2 stops16h 35mDelta
Sun 9/289:20 amSOU - MDW
2 stops18h 16mDelta
Deal found 8/12$2,856

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Southampton 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Southampton that are best for you.

Fly from

Midway

Fly to

Southampton

Route

Depart

Return

Price

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 11/18

1:00 pm-8:10 am

2 stops13h 10m

Southampton Eastleigh

Wed 11/26

8:40 am-6:07 pm

2 stops15h 27m

$936

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 11/19

1:00 pm-8:20 am

2 stops13h 20m

Southampton Eastleigh

Wed 11/26

8:40 am-6:07 pm

2 stops15h 27m

$936

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 11/19

1:00 pm-8:20 am

2 stops13h 20m

Southampton Eastleigh

Tue 12/2

5:30 pm-4:23 pm

2 stops28h 53m

$936

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 11/17

1:00 pm-8:10 am

2 stops13h 10m

Southampton Eastleigh

Wed 11/26

8:40 am-6:07 pm

2 stops15h 27m

$936

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 11/25

1:00 pm-8:10 am

2 stops13h 10m

Southampton Eastleigh

Tue 12/2

5:30 pm-4:23 pm

2 stops28h 53m

$936

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 10/31

1:08 pm-8:50 am

2 stops14h 42m

Southampton Eastleigh

Thu 11/13

8:50 am-6:07 pm

2 stops15h 17m

$1,138

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 12/23

10:08 am-8:10 am

2 stops16h 02m

Southampton Eastleigh

Mon 1/5

9:25 am-4:25 pm

2 stops37h 00m

$1,162

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 12/23

12:10 pm-8:10 am

2 stops14h 00m

Southampton Eastleigh

Thu 1/1

8:50 am-10:05 pm

2 stops19h 15m

$1,162

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 9/27

11:00 am-8:45 am

2 stops15h 45m

Southampton Eastleigh

Sat 10/4

9:20 am-6:35 pm

2 stops15h 15m

$1,640

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 8/25

10:31 am-8:50 am

2 stops16h 19m

Southampton Eastleigh

Thu 8/28

5:35 pm-5:37 pm

2 stops30h 02m

$1,916

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 16 results
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Best time to book a flight from Midway to Southampton

Have a flexible travel schedule? Discover the best time to fly to Southampton 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Southampton. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Southampton from Chicago Midway?

    Most people fly into Southampton Eastleigh (SOU) if they book a flight to Southampton from Chicago Midway. On average, Eastleigh has 0 inbound flights from Chicago Midway per day from 0 airlines. Southampton Eastleigh is conveniently located just 3.5 mi from Southampton’s city center.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Southampton 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 Southampton?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Southampton (average of $787). Flying from Chicago Midway Airport to Southampton in June is currently the most expensive (average of $1,308). 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 Southampton

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