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$414+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SOU
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
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Cheap 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 May 21, 2026.

This Delta deal was found by Cheapflights users on 5/18. 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.
Sun 7/196:58 pm
MDW
-
SOU
2 stops16h 37m
Delta
Fri 8/79:15 am
SOU
-
MDW
2 stops19h 21m
Delta
Deal found 5/18$1,174
This Delta deal was found by Cheapflights users on 5/18. 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 7/1810:55 am
MDW
-
SOU
2 stops15h 50m
Delta
Fri 8/79:15 am
SOU
-
MDW
2 stops19h 21m
Delta
Deal found 5/18$1,224
This Mytrip deal was found by Cheapflights users on 5/20. 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.
Fri 6/510:15 am
MDW
-
SOU
3 stops27h 15m
Multiple Airlines
Fri 6/199:25 am
SOU
-
MDW
3 stops30h 15m
Multiple Airlines
Deal found 5/20$1,413
This lastminute.com deal was found by Cheapflights users on 5/20. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:18 pm
MDW
-
SOU
2 stops13h 27m
Virgin Atlantic
Tue 8/46:05 pm
SOU
-
MDW
2 stops30h 28m
Virgin Atlantic
Deal found 5/20$1,462
This KLM deal was found by Cheapflights users on 5/19. 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 9/76:45 pm
MDW
-
SOU
2 stops16h 05m
KLM
Mon 9/219:05 am
SOU
-
MDW
2 stops18h 41m
KLM
Deal found 5/19$1,847
This Delta deal was found by Cheapflights users on 5/18. 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.
Fri 7/176:58 pm
MDW
-
SOU
2 stops16h 02m
Delta
Wed 8/59:15 am
SOU
-
MDW
2 stops14h 46m
Delta
Deal found 5/18$2,006
This Delta deal was found by Cheapflights users on 5/20. 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.
Fri 6/55:08 pm
MDW
-
SOU
2 stops17h 42m
Delta
Fri 6/199:05 am
SOU
-
MDW
2 stops15h 13m
Delta
Deal found 5/20$2,399
This KLM deal was found by Cheapflights users on 5/19. 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.
Tue 7/2811:05 am
MDW
-
SOU
2 stops15h 40m
KLM
Sun 8/99:15 am
SOU
-
MDW
2 stops19h 21m
KLM
Deal found 5/19$2,553
This KLM deal was found by Cheapflights users on 5/20. 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 8/77:25 pm
MDW
-
SOU
2 stops15h 35m
KLM
Mon 8/109:15 am
SOU
-
MDW
2 stops19h 21m
KLM
Deal found 5/20$2,604
This KLM deal was found by Cheapflights users on 5/20. 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 7/171:18 pm
MDW
-
SOU
2 stops13h 27m
KLM
Tue 8/49:15 am
SOU
-
MDW
2 stops14h 46m
KLM
Deal found 5/20$2,621
This Delta deal was found by Cheapflights users on 5/21. 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.
Fri 7/36:58 pm
MDW
-
SOU
2 stops16h 02m
Delta
Fri 7/109:15 am
SOU
-
MDW
2 stops15h 03m
Delta
Deal found 5/21$2,633

Find 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 May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,174
(Delta)

One-way from

$414
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$933
Provider with most accurate pricing for Chicago Midway-Southampton Eastleigh flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Southampton Eastleigh flights.
Search Deals
From Chicago Midway to Southampton Eastleigh
Search Deals
One-way flight from Chicago Midway to Southampton Eastleigh
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($274 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Southampton that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 9/7

6:45 pm-4:50 pm

2 stops16h 05m

Southampton Eastleigh

Mon 9/21

9:05 am-9:46 pm

2 stops18h 41m

$1,847

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 6/5

5:08 pm-4:50 pm

2 stops17h 42m

Southampton Eastleigh

Fri 6/19

9:05 am-6:18 pm

2 stops15h 13m

$2,399

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 7/29

11:05 am-8:45 am

2 stops15h 40m

Southampton Eastleigh

Sun 8/9

9:15 am-10:36 pm

2 stops19h 21m

$2,553

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 7/28

11:05 am-8:45 am

2 stops15h 40m

Southampton Eastleigh

Sun 8/9

9:15 am-10:36 pm

2 stops19h 21m

$2,553

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 8/7

7:25 pm-5:00 pm

2 stops15h 35m

Southampton Eastleigh

Mon 8/10

9:15 am-10:36 pm

2 stops19h 21m

$2,604

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 7/3

6:58 pm-5:00 pm

2 stops16h 02m

Southampton Eastleigh

Fri 7/10

9:15 am-6:18 pm

2 stops15h 03m

$2,633
Quickest round-trip

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Thu 7/16

1:18 pm-8:45 am

2 stops13h 27m

Southampton Eastleigh

Wed 8/5

9:15 am-6:01 pm

2 stops14h 46m

$2,635

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 7/15

1:18 pm-8:45 am

2 stops13h 27m

Southampton Eastleigh

Wed 8/5

9:15 am-6:01 pm

2 stops14h 46m

$2,961

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 7/15

9:19 am-8:45 am

2 stops17h 26m

Southampton Eastleigh

Mon 8/3

9:15 am-6:01 pm

2 stops14h 46m

$3,097
Cheapest one-way

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 7/11

10:25 am-11:50 am

3 stops43h 25m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/16

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Compare providers for flights from Midway to Southampton

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Southampton in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Southampton flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Southampton flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Southampton flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Southampton flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Southampton flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

    KLM and Delta can get you from Chicago Midway Airport to Southampton in just under 16h 05m. Your travel time can differ by up to 1h 37m. 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.

See more FAQs

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