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$807+ Cheap flights from Midway (MDW) to Southampton (SOU)

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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SOU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$807
(Delta)

Popular in

June

Cheapest in

February

Average price

$663
From Chicago Midway to Southampton Eastleigh
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($204 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).
Search Deals
Average for round-trip flights in September 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/9. 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 9/221:43 pmMDW - SOU
2 stops21h 17mDelta
Thu 9/259:20 amSOU - MDW
2 stops15h 15mDelta
Deal found 9/9$1,444
This KLM deal was found by Cheapflights users on 9/11. 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.
Wed 9/2410:35 amMDW - SOU
2 stops16h 10mKLM
Sat 9/279:20 amSOU - MDW
2 stops15h 15mKLM
Deal found 9/11$2,119
This Delta deal was found by Cheapflights users on 9/9. 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 9/139:35 amMDW - SOU
2 stops17h 10mDelta
Thu 10/29:20 amSOU - MDW
2 stops15h 15mDelta
Deal found 9/9$2,204
This Delta deal was found by Cheapflights users on 9/10. 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 10/259:20 amMDW - SOU
2 stops18h 30mDelta
Sat 11/19:25 amSOU - MDW
2 stops17h 49mDelta
Deal found 9/10$2,631
This KLM deal was found by Cheapflights users on 9/10. 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 9/131:08 pmMDW - SOU
2 stops13h 37mKLM
Thu 10/29:20 amSOU - MDW
2 stops15h 15mKLM
Deal found 9/10$2,878
This Mytrip deal was found by Cheapflights users on 9/11. 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.
Wed 9/249:20 amMDW - SOU
3 stops28h 05mMultiple Airlines
Sat 9/278:25 amSOU - MDW
3 stops30h 14mMultiple Airlines
Deal found 9/11$3,002
This Delta deal was found by Cheapflights users on 9/9. 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
Sun 9/289:20 amSOU - MDW
2 stops15h 15mDelta
Deal found 9/9$3,076

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 September 11, 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

Thu 2/26

9:20 am-8:50 am

2 stops41h 30m

Southampton Eastleigh

Mon 3/2

8:50 am-9:46 pm

2 stops42h 56m

$807

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 9/22

1:43 pm-5:00 pm

2 stops21h 17m

Southampton Eastleigh

Thu 9/25

9:20 am-6:35 pm

2 stops15h 15m

$1,444

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 9/24

10:35 am-8:45 am

2 stops16h 10m

Southampton Eastleigh

Sat 9/27

9:20 am-6:35 pm

2 stops15h 15m

$2,119

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 10/25

9:20 am-9:50 am

2 stops18h 30m

Southampton Eastleigh

Sat 11/1

9:25 am-10:14 pm

2 stops17h 49m

$2,631

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 9/24

9:20 am-7:25 pm

3 stops28h 05m

Southampton Eastleigh

Sat 9/27

8:25 am-8:39 am

3 stops30h 14m

$3,002

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

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.

  • How long is the flight from Chicago Midway Airport to Southampton?

    Delta and KLM can get you from Chicago Midway Airport to Southampton in just under 16h 10m. Your travel time can differ by up to 25h 20m. Airlines will cover a distance of 3924 mi. This flight may include one or multiple stops.

  • 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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