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$792+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SOU
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
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 January 26, 2026.

This Flysmarter deal was found by Cheapflights users on 1/25. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1612:45 pm
MDW
-
SOU
2 stops14h 05m
KLM
Wed 3/48:50 am
SOU
-
MDW
2 stops19h 41m
KLM
Deal found 1/25$792
This Delta deal was found by Cheapflights users on 1/25. 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 3/1112:47 pm
MDW
-
SOU
2 stops14h 33m
Delta
Wed 3/188:50 am
SOU
-
MDW
2 stops18h 41m
Delta
Deal found 1/25$1,096
This Mytrip deal was found by Cheapflights users on 1/25. 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 3/1111:00 am
MDW
-
SOU
3 stops25h 20m
Multiple Airlines
Wed 3/189:25 am
SOU
-
MDW
3 stops29h 40m
Multiple Airlines
Deal found 1/25$1,914
This KLM deal was found by Cheapflights users on 1/24. 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 7/46:45 pm
MDW
-
SOU
2 stops16h 15m
KLM
Sun 7/129:15 am
SOU
-
MDW
2 stops14h 50m
KLM
Deal found 1/24$8,344

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$792
(Flysmarter)

Popular in

June

Cheapest in

April

Average price

$666
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 ($203 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 26, 2026.
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

Mon 2/16

12:45 pm-8:50 am

2 stops14h 05m

Southampton Eastleigh

Wed 3/4

8:50 am-10:31 pm

2 stops19h 41m

$792

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 3/11

12:47 pm-8:20 am

2 stops14h 33m

Southampton Eastleigh

Wed 3/18

8:50 am-10:31 pm

2 stops18h 41m

$1,096

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 3/11

11:00 am-5:20 pm

3 stops25h 20m

Southampton Eastleigh

Wed 3/18

9:25 am-10:05 am

3 stops29h 40m

$1,914

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 7/4

6:45 pm-5:00 pm

2 stops16h 15m

Southampton Eastleigh

Sun 7/12

9:15 am-6:05 pm

2 stops14h 50m

$8,344

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 7/4

6:45 pm-5:00 pm

2 stops16h 15m

Southampton Eastleigh

Sun 7/12

9:15 am-6:05 pm

2 stops14h 50m

$8,344

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 6/23

5:25 pm-4:50 pm

2 stops17h 25m

$6,027

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 14h 05m. Your travel time can differ by up to 28m. 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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