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Cheap flights from London Southend Airport to Chicago from £396

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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
18 Oct — 25 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Southend to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Southend (SEN) 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 18 September 2025.

Round-trip from

£706

One-way from

£396

Popular in

July

Cheapest in

February

Average price

£434
1/11-8/11
  • 1/11-8/11
  • 3 total stops
  • 57h 35m total
  • London to Chicago
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20/10
  • 20/10
  • 3 total stops
  • 46h 40m total
  • London to Chicago
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Highest demand for flights based on searches. 14% potential increase in price (£60 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£9 potential savings vs. average return price).
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Average for round-trip flights in September 2025
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Find flight deals from Southend to Chicago

Cheapest flights from Southend to Chicago
Explore the most affordable flight options available from Southend to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 September 2025.

Sat 1/1108:40SEN - ORD
2 stops36h 05mMultiple Airlines
Sat 8/1117:20ORD - SEN
1 stop21h 30mMultiple Airlines
Deal found 16/9£706
Sat 20/1207:15SEN - ORD
1 stop13h 05mMultiple Airlines
Sat 27/1217:20ORD - SEN
2 stops20h 50mMultiple Airlines
Deal found 15/9£942

Cheapflights Fare Finder

 
Customise your flight search to find flights from Southend 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 18 September 2025.
Use the filters below to find and compare flights from London Southend Airport to Chicago that are best for you.

Fly from

Southend

Fly to

Chicago

Route

Depart

Return

Price

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 1/11

08:40-15:45

2 stops36h 05m

Chicago O'Hare Intl

Sat 8/11

17:20-20:50

1 stop21h 30m

£706

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 20/12

07:15-14:20

1 stop13h 05m

Chicago O'Hare Intl

Sat 27/12

17:20-20:10

2 stops20h 50m

£942

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 20/10

20:05-12:45

3 stops46h 40m

£396

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 25/10

17:30-15:45

3 stops28h 15m

£399

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 25/9

06:30-16:30

2 stops40h 00m

£402

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 22/9

20:05-09:18

3 stops43h 13m

£412

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 6/10

11:05-09:43

3 stops28h 38m

£422

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 26/10

08:00-09:22

3 stops30h 22m

£437

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 1/11

07:15-18:55

2 stops16h 40m

£440

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 17/10

07:55-21:00

3 stops43h 05m

£441

Flights are sorted by cheapest return flights first.

Deals found on 17/9

Showing 1-10 of 11 results
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Best time to book a flight from Southend to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Southend 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 London Southend Airport to Chicago
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Southend to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Southend 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 London Southend Airport to Chicago?

    Currently, January is the cheapest month in which you can book a flight from London Southend Airport to Chicago (average of £595). Flying from London Southend Airport 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 Southend 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 Southend to Chicago?

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

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

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

Yes! Start tracking prices for Southend to Chicago 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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