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$803+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SOU
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This KLM deal was found by Cheapflights users on 12/2. 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 12/309:29 amMDW - SOU
2 stops16h 41mKLM
Tue 1/65:35 pmSOU - MDW
2 stops34h 32mKLM
Deal found 12/2$1,120
This Delta deal was found by Cheapflights users on 12/3. 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 12/1910:49 amMDW - SOU
2 stops16h 01mDelta
Tue 12/238:40 amSOU - MDW
2 stops19h 42mDelta
Deal found 12/3$2,520
This Mytrip deal was found by Cheapflights users on 12/3. 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 12/1911:00 amMDW - SOU
3 stops24h 00mMultiple Airlines
Tue 12/238:40 amSOU - MDW
3 stops31h 25mMultiple Airlines
Deal found 12/3$3,393

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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$829
(KLM)

Popular in

June

Cheapest in

February

Average price

$807
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
Highest demand for flights based on searches. 21% potential increase in price ($206 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 4, 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

Fri 1/16

6:45 am-8:45 am

2 stops20h 00m

Southampton Eastleigh

Tue 1/20

5:35 pm-6:36 pm

2 stops31h 01m

$803

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sun 1/18

9:50 am-8:50 am

2 stops17h 00m

Southampton Eastleigh

Sun 1/25

5:45 pm-5:29 pm

2 stops29h 44m

$829

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 1/17

5:31 pm-5:15 pm

2 stops17h 44m

Southampton Eastleigh

Sat 1/24

9:25 am-10:22 pm

2 stops18h 57m

$924

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 12/30

9:29 am-8:10 am

2 stops16h 41m

Southampton Eastleigh

Tue 1/6

5:35 pm-10:07 pm

2 stops34h 32m

$1,120

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 1/16

1:28 pm-8:45 am

2 stops13h 17m

Southampton Eastleigh

Fri 1/23

9:00 am-10:22 pm

2 stops19h 22m

$1,326

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 12/19

10:49 am-8:50 am

2 stops16h 01m

Southampton Eastleigh

Tue 12/23

8:40 am-10:22 pm

2 stops19h 42m

$2,520

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 12/19

11:00 am-5:00 pm

3 stops24h 00m

Southampton Eastleigh

Tue 12/23

8:40 am-10:05 am

3 stops31h 25m

$3,393

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Southampton flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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?

    Virgin Atlantic and KLM can get you from Chicago Midway Airport to Southampton in just under 17h. Your travel time can differ by up to 3h. 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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