Find flights
When to book
FAQs

Cheap flights from Southampton to Chicago Midway Airport from £326

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 16/1. Fares are subject to change and may not be available on all flights or dates of travel.
SOU — MDW
4 Jan — 11 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Southampton to Midway

Enter your travel dates to find the best prices.

Best flights from Southampton to Midway
Discover carefully curated flight deals from Southampton to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 5 December 2025.

Fri 16/109:00SOU - MDW
2 stops19h 07mDelta
Fri 23/113:26MDW - SOU
2 stops13h 19mDelta
Deal found 2/12£570
Sun 18/117:45SOU - MDW
2 stops29h 44mKLM
Sun 25/110:48MDW - SOU
2 stops16h 02mKLM
Deal found 3/12£635
Wed 4/209:25SOU - MDW
2 stops30h 28mDelta
Sun 8/213:26MDW - SOU
2 stops21h 39mDelta
Deal found 1/12£590

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 5 December 2025.

Round-trip from

£570

One-way from

£326

Popular in

July

Cheapest in

February

Average price

£599
Delta
  • Delta
  • 16/1-23/1
  • 4 total stops
  • 32h 26m total
  • Southampton to Chicago
Search Deals
16/1
  • 16/1
  • 3 total stops
  • 53h 20m total
  • Southampton to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£59 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 December 2025
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 5 December 2025.
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

Fri 16/1

09:00-22:07

2 stops19h 07m

Chicago Midway

Fri 23/1

13:26-08:45

2 stops13h 19m

£570

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 4/2

09:25-09:53

2 stops30h 28m

Chicago Midway

Sun 8/2

13:26-17:05

2 stops21h 39m

£590

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 18/1

17:45-17:29

2 stops29h 44m

Chicago Midway

Sun 25/1

10:48-08:50

2 stops16h 02m

£635

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 16/1

17:45-17:05

3 stops53h 20m

£326

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sat 17/1

09:25-17:34

2 stops38h 09m

£1,265

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 19/12

08:40-23:47

2 stops21h 07m

£1,520

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 18/12

08:50-18:18

2 stops15h 28m

£1,610

Flights are sorted by cheapest return flights first.

Deals found on 2/12

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 £421). Flying from Southampton to Chicago Midway Airport in December is currently the most expensive (average of £780). 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 £570, Delta can have you in Chicago Midway Airport from Southampton in 19h 07m. 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 £421). Flying from Southampton to Chicago Midway Airport in December is currently the most expensive (average of £780). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Southampton to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Heathrow to O'Hare Intl flights
Gatwick to O'Hare Intl flights
London City to O'Hare Intl flights
Heathrow to Midway flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Gatwick to Midway flights
Manchester to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to Midway flights
Birmingham to Midway flights
Leeds to O'Hare Intl flights
London City to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Southampton to O'Hare Intl flights
Southend to O'Hare Intl flights
Bristol to O'Hare Intl flights
Leeds to Midway flights
Newcastle upon Tyne to Midway flights
Newquay to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Exeter to O'Hare Intl flights
Darlington to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Bristol to Midway flights
Doncaster to O'Hare Intl flights
Darlington to Midway flights
Norwich to O'Hare Intl 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.