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Cheap flights from Southampton to Chicago Midway Airport from £419

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 13/9. Fares are subject to change and may not be available on all flights or dates of travel.
SOU — MDW
4 Jul — 11 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Southampton to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Southampton to Midway
Explore the most affordable flight options available from Southampton to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4 June 2026.

Wed 17/609:05
SOU
-
MDW
2 stops29h 32m
Delta
Fri 4/917:10
MDW
-
SOU
2 stops17h 40m
Delta
Deal found 3/6£905
Fri 19/617:20
SOU
-
MDW
2 stops30h 51m
Virgin Atlantic
Fri 4/913:27
MDW
-
SOU
2 stops21h 23m
Virgin Atlantic
Deal found 3/6£935
Fri 19/609:05
SOU
-
MDW
2 stops15h 13m
Delta
Mon 31/809:59
MDW
-
SOU
2 stops16h 36m
Delta
Deal found 2/6£1,065
Thu 18/609:05
SOU
-
MDW
2 stops19h 12m
KLM
Fri 4/912:46
MDW
-
SOU
2 stops13h 59m
KLM
Deal found 3/6£1,224
Fri 31/709:15
SOU
-
MDW
2 stops15h 03m
Multiple Airlines
Wed 5/812:46
MDW
-
SOU
2 stops13h 59m
Multiple Airlines
Deal found 3/6£1,237
Mon 15/609:05
SOU
-
MDW
2 stops19h 12m
Delta
Sun 21/618:58
MDW
-
SOU
2 stops15h 52m
Delta
Deal found 2/6£1,245
Sat 20/609:15
SOU
-
MDW
2 stops14h 39m
KLM
Fri 4/912:46
MDW
-
SOU
2 stops13h 59m
KLM
Deal found 3/6£1,495
Thu 16/709:15
SOU
-
MDW
2 stops15h 03m
KLM
Thu 23/713:18
MDW
-
SOU
2 stops13h 27m
KLM
Deal found 1/6£1,647
Fri 17/709:15
SOU
-
MDW
2 stops15h 03m
Delta
Fri 24/709:54
MDW
-
SOU
2 stops16h 51m
Delta
Deal found 3/6£1,826

Find flight deals from Southampton to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Southampton (SOU) to Midway (MDW). 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 4 June 2026.

Round-trip from

£905

One-way from

£419

Popular in

July

Cheapest in

February

Average price

£566
Delta
  • Delta
  • 17/6-4/9
  • 4 total stops
  • 47h 12m total
  • Southampton to Chicago
Search Deals
13/9
  • 13/9
  • 3 total stops
  • 43h 07m total
  • Southampton to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£55 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£9 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Southampton to Midway 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 858,174 searches. Data last updated 4 June 2026.
Use the filters below to find and compare flights from Southampton to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 22/6

17:20-18:31

2 stops31h 11m

Chicago Midway

Fri 4/9

17:10-16:50

2 stops17h 40m

£905

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 19/6

17:20-18:11

2 stops30h 51m

Chicago Midway

Fri 4/9

13:27-16:50

2 stops21h 23m

£935

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 19/6

09:05-18:18

2 stops15h 13m

Chicago Midway

Mon 31/8

09:59-08:35

2 stops16h 36m

£1,065

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 18/6

09:05-22:17

2 stops19h 12m

Chicago Midway

Fri 4/9

12:46-08:45

2 stops13h 59m

£1,224

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 31/7

09:15-18:18

2 stops15h 03m

Chicago Midway

Wed 5/8

12:46-08:45

2 stops13h 59m

£1,237

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 15/6

09:05-22:17

2 stops19h 12m

Chicago Midway

Sun 21/6

18:58-16:50

2 stops15h 52m

£1,245
Fastest return journey

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 16/7

09:15-18:18

2 stops15h 03m

Chicago Midway

Thu 23/7

13:18-08:45

2 stops13h 27m

£1,647

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 17/7

09:15-18:18

2 stops15h 03m

Chicago Midway

Fri 24/7

09:54-08:45

2 stops16h 51m

£1,826
Cheapest one-way

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 13/9

20:00-09:07

3 stops43h 07m

£419

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 13/9

09:15-21:46

2 stops18h 31m

£1,391

Flights are sorted by cheapest return flights first.

Deals found on 3/6

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Best time to book a flight from Southampton to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Southampton with our price prediction graph.
Estimated return 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 Southampton to Midway. 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 from for flights from Southampton to Chicago Midway?

    Southampton Eastleigh (SOU), located 3.5 mi from the city center, is the airport you fly out of when you book flights from Southampton to Chicago Midway. 0 airlines have flights from Eastleigh to Chicago Midway on a regular basis. Booking flights from Southampton Eastleigh to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    For as low as £1,224, Delta can have you in Chicago Midway Airport from Southampton in 19h 12m. The distance from Southampton to Chicago Midway Airport is about 3924 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Southampton to Midway 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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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Southampton to Midway?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Southampton to Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Southampton to Midway?

Cheapflights helps you find that perfect flight to Midway from Southampton by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Southampton to Midway with no change fees?

Yes, we can. To see specific flights from Southampton to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Southampton to Midway become cheaper?

Yes! Start tracking prices for Southampton to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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