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Cheap flights from Southampton to Chicago from £536

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Southampton to Chicago departing on 15/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Southampton to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
KLM Logo
09:05 - 18:19SOU  Southampton Eastleigh-MDW Chicago Midway
15h 14m2 stops Amsterdam Schiphol Minneapolis St Paul
KLM Logo
19:01 - 16:50MDW  Chicago Midway-SOU Southampton Eastleigh
15h 49m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£680KLM
Tue, 8 Sep - Mon, 14 Sep
Delta Logo
08:40 - 22:56SOU  Southampton Eastleigh-MDW Chicago Midway
20h 16m2 stops Amsterdam Schiphol Atlanta Hartsfield-Jackson
Delta Logo
13:22 - 08:10MDW  Chicago Midway-SOU Southampton Eastleigh
12h 48m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£722Delta
Mon, 16 Nov - Tue, 24 Nov
Delta Logo
09:05 - 18:19SOU  Southampton Eastleigh-MDW Chicago Midway
15h 14m2 stops Amsterdam Schiphol Minneapolis St Paul
Delta Logo
19:01 - 16:50MDW  Chicago Midway-SOU Southampton Eastleigh
15h 49m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£731Delta
Tue, 8 Sep - Mon, 14 Sep
Virgin Atlantic Logo
17:20 - 18:33SOU  Southampton Eastleigh-MDW Chicago Midway
31h 13m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
Virgin Atlantic Logo
19:01 - 16:50MDW  Chicago Midway-SOU Southampton Eastleigh
15h 49m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£745Virgin Atlantic
Mon, 14 Sep - Sun, 20 Sep
Virgin Atlantic Logo
09:15 - 17:59SOU  Southampton Eastleigh-MDW Chicago Midway
14h 44m2 stops Amsterdam Schiphol Minneapolis St Paul
Virgin Atlantic Logo
09:59 - 08:45MDW  Chicago Midway-SOU Southampton Eastleigh
16h 46m2 stops Minneapolis St Paul Amsterdam Schiphol
£782Virgin Atlantic
Sat, 26 Sep - Sat, 3 Oct
Virgin Atlantic Logo
09:15 - 22:44SOU  Southampton Eastleigh-MDW Chicago Midway
19h 29m2 stops Amsterdam Schiphol Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
13:19 - 08:45MDW  Chicago Midway-SOU Southampton Eastleigh
13h 26m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£836Virgin Atlantic
Sat, 26 Sep - Sat, 3 Oct
KLM Logo
09:05 - 18:19SOU  Southampton Eastleigh-MDW Chicago Midway
15h 14m2 stops Amsterdam Schiphol Minneapolis St Paul
KLM Logo
13:19 - 08:35MDW  Chicago Midway-SOU Southampton Eastleigh
13h 16m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£1,056KLM
Mon, 28 Sep - Mon, 5 Oct
Virgin Atlantic Logo
17:20 - 18:33SOU  Southampton Eastleigh-MDW Chicago Midway
31h 13m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
Virgin Atlantic Logo
13:19 - 08:35MDW  Chicago Midway-SOU Southampton Eastleigh
13h 16m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
£1,428Virgin Atlantic
Mon, 28 Sep - Mon, 5 Oct

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Delta flights from Southampton to Chicago Midway Airport

Our best Delta deals on Southampton to Chicago Midway Airport flight tickets
Delta
16 Nov
SOU08:40Southampton Eastleigh
20h 16m
2 stops
MDW22:56Chicago Midway
24 Nov
MDW13:22Chicago Midway
12h 48m
2 stops
SOU08:10Southampton Eastleigh
£722
Delta
8 Sept
SOU09:05Southampton Eastleigh
15h 14m
2 stops
MDW18:19Chicago Midway
14 Sept
MDW19:01Chicago Midway
15h 49m
2 stops
SOU16:50Southampton Eastleigh
£731

Virgin Atlantic flights from Southampton to Chicago Midway Airport

Our best Virgin Atlantic deals on Southampton to Chicago Midway Airport flight tickets
Virgin Atlantic
14 Sept
SOU17:20Southampton Eastleigh
31h 13m
2 stops
MDW18:33Chicago Midway
20 Sept
MDW19:01Chicago Midway
15h 49m
2 stops
SOU16:50Southampton Eastleigh
£745
Virgin Atlantic
26 Sept
SOU09:15Southampton Eastleigh
19h 29m
2 stops
MDW22:44Chicago Midway
3 Oct
MDW13:19Chicago Midway
13h 26m
2 stops
SOU08:45Southampton Eastleigh
£836
Virgin Atlantic
28 Sept
SOU17:20Southampton Eastleigh
31h 13m
2 stops
MDW18:33Chicago Midway
5 Oct
MDW13:19Chicago Midway
13h 16m
2 stops
SOU08:35Southampton Eastleigh
£1,428

momondo Fare Finder

 
Customise your flight search to find flights from Southampton to Chicago Midway Airport 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, momondo users made 279,928 searches. Data last updated 15 August 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 Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Tue 8/9

09:05-18:19

2 stops15h 14m

Chicago Midway

Mon 14/9

19:01-16:50

2 stops15h 49m

£680

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Mon 16/11

08:40-22:56

2 stops20h 16m

Chicago Midway

Tue 24/11

13:22-08:10

2 stops12h 48m

£722

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Tue 8/9

09:05-18:19

2 stops15h 14m

Chicago Midway

Mon 14/9

19:01-16:50

2 stops15h 49m

£731

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Mon 14/9

17:20-18:33

2 stops31h 13m

Chicago Midway

Sun 20/9

19:01-16:50

2 stops15h 49m

£745

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Sat 26/9

09:15-17:59

2 stops14h 44m

Chicago Midway

Sat 3/10

09:59-08:45

2 stops16h 46m

£782

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Sat 26/9

09:15-22:44

2 stops19h 29m

Chicago Midway

Sat 3/10

13:19-08:45

2 stops13h 26m

£836
Fastest return journey

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Mon 28/9

09:05-18:19

2 stops15h 14m

Chicago Midway

Mon 5/10

13:19-08:35

2 stops13h 16m

£1,056

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Mon 28/9

17:20-18:33

2 stops31h 13m

Chicago Midway

Mon 5/10

13:19-08:35

2 stops13h 16m

£1,428
Cheapest one-way

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Tue 15/9

20:00-09:07

3 stops43h 07m

£536

SouthamptonChicago

SOU Southampton Eastleigh - MDW Chicago Midway

SOUMDW

Southampton Eastleigh

Tue 1/9

20:00-14:35

3 stops48h 35m

£574

Flights are sorted by cheapest return flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Southampton to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Southampton Eastleigh to Chicago Midway?

KLM is the most popular carrier operating from Southampton Eastleigh to Chicago Midway

When to book flights from Southampton to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Southampton to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Southampton to Chicago Midway Airport (SOU to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Southampton to Chicago Midway Airport

Fastest flight time

31h 13m

Direct flights

None
The fastest flight from Southampton to Chicago Midway Airport takes 31h 13m
There are no direct flights from Southampton to Chicago Midway Airport. There are no popular flight routes from Southampton to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Southampton to Chicago Midway Airport

  • How far is Southampton Eastleigh to Chicago Midway by plane?

    Chicago Midway is 3923.6 mi away from Southampton Eastleigh. A reasonable flight in good conditions will take 31h 13m.

  • When did momondo last update prices for flights from Southampton Eastleigh Airport to Chicago Midway Airport?

    Prices for flights from Southampton Eastleigh Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Southampton Eastleigh Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Southampton Eastleigh Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schererville

Why use momondo?

Why should I use momondo to find a flight deal from Southampton to Chicago?

Finding the right flight to Chicago from Southampton is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Southampton to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Southampton to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Southampton to Chicago?

momondo helps you find the best flight between Southampton and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Southampton to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Southampton. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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