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Cheap flights from Southampton to Chicago from £497

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 30/10. Fares are subject to change and may not be available on all flights or dates of travel.
SOU — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Southampton to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Southampton (SOU) to Chicago (CHI). 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 17 September 2025.

Round-trip from

£497

Popular in

July

Cheapest in

February

Average price

£435
KLM
  • KLM
  • 30/10-6/11
  • 3 total stops
  • 39h 12m total
  • Southampton to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£61 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 September 2025
Search Deals

Find flight deals from Southampton to Chicago

Cheapest flights from Southampton to Chicago
Explore the most affordable flight options available from Southampton to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 September 2025.

Thu 30/1018:05SOU - ORD
1 stop26h 15mKLM
Thu 6/1113:08ORD - SOU
2 stops12h 57mKLM
Deal found 15/9£497
Fri 31/1017:30SOU - ORD
1 stop26h 50mKLM
Fri 7/1116:25ORD - SOU
1 stop10h 25mKLM
Deal found 16/9£499
Fri 31/1008:40SOU - MDW
2 stops18h 34mDelta
Fri 7/1110:40MDW - SOU
2 stops16h 10mDelta
Deal found 16/9£513
Thu 30/1008:50SOU - MDW
2 stops38h 05mKLM
Thu 6/1113:08MDW - SOU
2 stops12h 57mKLM
Deal found 15/9£524
Thu 30/1020:10SOU - ORD
2 stops29h 55mMultiple Airlines
Thu 6/1118:50ORD - SOU
3 stops35h 05mMultiple Airlines
Deal found 15/9£585
Fri 31/1014:25SOU - ORD
2 stops32h 20mMultiple Airlines
Fri 7/1119:20ORD - SOU
3 stops31h 25mMultiple Airlines
Deal found 16/9£757
Sat 27/1209:30SOU - ORD
1 stop14h 25mBritish Airways
Sat 17/121:00ORD - SOU
1 stop12h 35mBritish Airways
Deal found 16/9£847
Tue 30/919:55SOU - ORD
2 stops21h 55mBritish Airways
Tue 7/1015:45ORD - SOU
1 stop10h 20mBritish Airways
Deal found 16/9£893

Cheapflights Fare Finder

 
Customise your flight search to find flights from Southampton to Chicago 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 17 September 2025.
Use the filters below to find and compare flights from Southampton to Chicago that are best for you.

Fly from

Southampton

Fly to

Chicago

Route

Depart

Return

Price

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 30/10

18:05-15:20

1 stop26h 15m

Chicago O'Hare Intl

Thu 6/11

13:08-08:05

2 stops12h 57m

£497

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 31/10

17:30-15:20

1 stop26h 50m

Chicago O'Hare Intl

Fri 7/11

16:25-08:50

1 stop10h 25m

£499

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 31/10

08:40-22:14

2 stops18h 34m

Chicago Midway

Fri 7/11

10:40-08:50

2 stops16h 10m

£513

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 30/10

08:50-17:55

2 stops38h 05m

Chicago Midway

Thu 6/11

13:08-08:05

2 stops12h 57m

£524

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 5/3

18:05-14:20

1 stop26h 15m

Chicago O'Hare Intl

Mon 9/3

17:25-17:00

1 stop18h 35m

£533

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 5/3

18:05-16:25

2 stops28h 20m

Chicago Midway

Mon 9/3

17:25-08:10

2 stops33h 45m

£537

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Mon 22/12

12:05-17:55

2 stops35h 50m

£576

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 23/12

15:20-06:25

3 stops45h 05m

£658

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 5/10

20:00-19:29

2 stops29h 29m

£706

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 30/9

20:00-19:00

1 stop29h 00m

£710

Flights are sorted by cheapest return flights first.

Deals found on 16/9

Showing 1-10 of 13 results
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Best time to book a flight from Southampton to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, January is the cheapest month in which you can book a flight from Southampton to Chicago (average of £595). Flying from Southampton to Chicago in July is currently the most expensive (average of £843). 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.

What’s the top stopover airport for flights from Southampton to Chicago?

Share of one-stop return flights from Southampton to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.

Amsterdam (AMS) – chosen by Cheapflights users on 60% of one-stop itineraries from Southampton to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Southampton to Chicago?

Average return fare for one-stop flights from Southampton to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

Dublin (DUB) is the most affordable one-stop option, with an average return flight price of £538.

What’s the fastest stopover option from Southampton to Chicago?

Shortest average travel time for one-stop one-way flights from Southampton to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via Amsterdam (AMS) have the shortest average one-way travel time for one-stop routes: 11h 03m.

Which airport typically offers the quickest stopover for flights from Southampton to Chicago?

Average stopover duration for one-stop one-way flights from Southampton to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Amsterdam (AMS) offer the fastest connection on this route, with an average stopover time of 1h 17m.

Related info for your journey

Find useful and relevant information for your journey from Southampton to Chicago. 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?

    Southampton Eastleigh (SOU) is the airport you will fly out of if you book a flight from Southampton to Chicago. You should not have trouble finding flights to Chicago from Eastleigh; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Southampton airport to Chicago. It is only a 3.5 mi journey to Eastleigh (SOU) from Southampton’s city center.

  • How long is the flight from Southampton to Chicago?

    KLM and Delta can get you from Southampton to Chicago in just under 18h 34m. Your travel time can differ by up to 7h 41m. The distance between Southampton and Chicago is about 3924 mi. Both multi-stop and direct flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Southampton to Chicago 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?

    Currently, January is the cheapest month in which you can book a flight from Southampton to Chicago (average of £595). Flying from Southampton to Chicago in July is currently the most expensive (average of £843). 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 Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Fly with Cheapflights

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Southampton today with Cheapflights!

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Southampton to Chicago.

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Southampton to Chicago, users can toggle the no change fees filter when performing a flight search.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Southampton today and book when prices fit your budget.

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