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Cheap flights from Southampton to Chicago Midway Airport from £418

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
SOU — MDW
15 May — 22 May1
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 15 April 2026.

Thu 17/909:05
SOU
-
MDW
2 stops18h 41m
Delta
Tue 22/917:25
MDW
-
SOU
2 stops17h 25m
Delta
Deal found 14/4£737
Thu 8/1017:20
SOU
-
MDW
2 stops31h 17m
Virgin Atlantic
Tue 13/1013:00
MDW
-
SOU
2 stops21h 50m
Virgin Atlantic
Deal found 11/4£763
Wed 27/509:05
SOU
-
MDW
2 stops15h 28m
KLM
Wed 3/613:22
MDW
-
SOU
2 stops13h 13m
KLM
Deal found 12/4£804
Fri 29/509:25
SOU
-
MDW
3 stops30h 20m
Multiple Airlines
Fri 5/610:25
MDW
-
SOU
3 stops27h 05m
Multiple Airlines
Deal found 14/4£850
Thu 28/509:05
SOU
-
MDW
2 stops15h 28m
Delta
Thu 4/609:23
MDW
-
SOU
2 stops17h 12m
Delta
Deal found 13/4£852
Tue 26/517:20
SOU
-
MDW
2 stops30h 36m
KLM
Tue 2/613:59
MDW
-
SOU
2 stops20h 51m
KLM
Deal found 11/4£854
Fri 29/517:20
SOU
-
MDW
2 stops31h 13m
Virgin Atlantic
Fri 5/619:13
MDW
-
SOU
2 stops31h 32m
Virgin Atlantic
Deal found 14/4£886
Mon 20/409:05
SOU
-
MDW
2 stops15h 31m
Delta
Mon 4/518:38
MDW
-
SOU
2 stops16h 12m
Delta
Deal found 11/4£1,009
Thu 8/1020:00
SOU
-
MDW
3 stops28h 37m
Multiple Airlines
Tue 13/1017:59
MDW
-
SOU
3 stops32h 36m
Multiple Airlines
Deal found 11/4£1,426
Thu 28/509:05
SOU
-
MDW
2 stops14h 51m
KLM
Thu 4/613:22
MDW
-
SOU
2 stops13h 13m
KLM
Deal found 13/4£1,478
Thu 8/1009:05
SOU
-
MDW
2 stops18h 40m
Delta
Tue 13/1009:55
MDW
-
SOU
2 stops16h 40m
Delta
Deal found 11/4£1,561

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 15 April 2026.

Round-trip from

£737

One-way from

£418

Popular in

July

Cheapest in

September

Average price

£537
Delta
  • Delta
  • 17/9-22/9
  • 4 total stops
  • 36h 06m total
  • Southampton to Chicago
Search Deals
11/5
  • 11/5
  • 3 total stops
  • 28h 33m total
  • Southampton to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£50 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 April 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 15 April 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

Thu 17/9

09:05-21:46

2 stops18h 41m

Chicago Midway

Wed 23/9

10:35-08:35

2 stops16h 00m

£737

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 17/9

09:05-21:46

2 stops18h 41m

Chicago Midway

Tue 22/9

17:25-16:50

2 stops17h 25m

£737

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 8/10

17:20-18:37

2 stops31h 17m

Chicago Midway

Tue 13/10

13:00-16:50

2 stops21h 50m

£763

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 27/5

09:05-18:33

2 stops15h 28m

Chicago Midway

Wed 3/6

13:22-08:35

2 stops13h 13m

£804

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Tue 26/5

17:20-17:56

2 stops30h 36m

Chicago Midway

Tue 2/6

13:59-16:50

2 stops20h 51m

£854

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 29/5

17:20-18:33

2 stops31h 13m

Chicago Midway

Fri 5/6

19:13-08:45

2 stops31h 32m

£886

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 8/10

20:00-18:37

3 stops28h 37m

Chicago Midway

Tue 13/10

17:59-08:35

3 stops32h 36m

£1,426
Fastest return journey

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 28/5

09:05-17:56

2 stops14h 51m

Chicago Midway

Thu 4/6

13:22-08:35

2 stops13h 13m

£1,478

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 8/10

09:05-21:45

2 stops18h 40m

Chicago Midway

Tue 13/10

09:55-08:35

2 stops16h 40m

£1,561
Cheapest one-way

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 11/5

09:05-18:33

2 stops15h 28m

£1,348

Flights are sorted by cheapest return flights first.

Deals found on 11/4

Showing 1-10 of 12 resultsSorted by cheapest first
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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 £804, Delta can have you in Chicago Midway Airport from Southampton in 15h 28m. 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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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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