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Cheap flights from Southampton to Chicago Midway Airport from £520

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/2. Fares are subject to change and may not be available on all flights or dates of travel.
SOU — MDW
12 Feb — 19 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap 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 13 January 2026.

Round-trip from

£520

Popular in

July

Cheapest in

February

Average price

£464
KLM
  • KLM
  • 28/1-1/2
  • 4 total stops
  • 34h 59m total
  • Southampton to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£65 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 2026
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Find 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 13 January 2026.

Wed 28/109:25
SOU
-
MDW
2 stops18h 57m
KLM
Sun 1/210:48
MDW
-
SOU
2 stops16h 02m
KLM
Deal found 12/1£520
Thu 5/209:00
SOU
-
MDW
2 stops14h 55m
KLM
Thu 12/209:34
MDW
-
SOU
2 stops16h 51m
KLM
Deal found 12/1£560
Tue 27/109:25
SOU
-
MDW
2 stops18h 57m
Delta
Sat 31/113:26
MDW
-
SOU
2 stops21h 49m
Delta
Deal found 11/1£1,139

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

Fly from

Southampton

Fly to

Midway

Route

Depart

Return

Price

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 25/2

08:50-18:40

2 stops15h 50m

Chicago Midway

Wed 4/3

10:49-08:20

2 stops15h 31m

£520

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 28/1

09:25-22:22

2 stops18h 57m

Chicago Midway

Sun 1/2

10:48-08:50

2 stops16h 02m

£520

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 5/2

09:00-17:55

2 stops14h 55m

Chicago Midway

Thu 12/2

09:34-08:25

2 stops16h 51m

£560

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Tue 27/1

09:25-22:22

2 stops18h 57m

Chicago Midway

Sat 31/1

13:26-17:15

2 stops21h 49m

£1,139

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 8/2

17:45-17:29

2 stops29h 44m

Chicago Midway

Sat 14/2

16:13-17:15

2 stops19h 02m

£1,139

Flights are sorted by cheapest return flights first.

Deals found on 11/1

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.

Cheapflights Insights

Everything you need to know about your flight from Southampton to Chicago Midway Airport

What is the cheapest month to book a flight from Southampton to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Southampton to Chicago Midway Airport (average of £418). Flying from Southampton to Chicago Midway Airport in December is currently the most expensive (average of £774). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 £520, Delta can have you in Chicago Midway Airport from Southampton in 15h 50m. 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.

  • What is the cheapest month to book a flight from Southampton to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Southampton to Chicago Midway Airport (average of £418). Flying from Southampton to Chicago Midway Airport in December is currently the most expensive (average of £774). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Southampton to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Darlington to Midway flights

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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