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Cheap flights from London Southend Airport to Chicago from £442

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
30 Nov — 7 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Southend to Chicago

Enter your travel dates to find the best prices.

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 31 October 2025.

Thu 4/1206:50SEN - ORD
2 stops17h 35mMultiple Airlines
Mon 8/1218:50ORD - SEN
2 stops18h 55mMultiple Airlines
Deal found 29/10£442
Wed 10/1207:10SEN - ORD
2 stops16h 10mMultiple Airlines
Wed 10/1221:50ORD - SEN
2 stops17h 10mMultiple Airlines
Deal found 30/10£904
Sun 21/1207:10SEN - ORD
2 stops16h 45mMultiple Airlines
Mon 29/1218:50ORD - SEN
2 stops18h 55mMultiple Airlines
Deal found 29/10£907
Mon 3/1107:15SEN - ORD
2 stops16h 05mMultiple Airlines
Tue 11/1110:35ORD - SEN
2 stops17h 25mMultiple Airlines
Deal found 29/10£915
Wed 3/1207:10SEN - ORD
2 stops16h 10mMultiple Airlines
Wed 17/1218:30ORD - SEN
2 stops20h 30mMultiple Airlines
Deal found 30/10£922
Tue 23/1207:35SEN - ORD
2 stops16h 20mMultiple Airlines
Sun 4/118:30ORD - SEN
2 stops14h 20mMultiple Airlines
Deal found 29/10£961
Mon 1/1207:15SEN - ORD
1 stop13h 55mMultiple Airlines
Thu 11/1217:20ORD - SEN
1 stop13h 30mMultiple Airlines
Deal found 30/10£983
Tue 23/1207:35SEN - ORD
2 stops16h 20mMultiple Airlines
Sat 3/121:50ORD - SEN
2 stops16h 20mMultiple Airlines
Deal found 29/10£1,075
Sat 29/1107:15SEN - ORD
1 stop13h 05mMultiple Airlines
Sat 6/1217:20ORD - SEN
2 stops20h 50mMultiple Airlines
Deal found 29/10£1,207
Fri 31/1008:00SEN - ORD
2 stops15h 20mMultiple Airlines
Sun 2/1117:20ORD - SEN
1 stop11h 10mMultiple Airlines
Deal found 29/10£1,347
Sat 20/1207:15SEN - ORD
2 stops16h 05mMultiple Airlines
Sat 3/121:50ORD - SEN
2 stops16h 20mMultiple Airlines
Deal found 30/10£1,406
Mon 3/1107:30SEN - ORD
2 stops16h 25mMultiple Airlines
Fri 7/1116:25ORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 29/10£1,498

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 31 October 2025.

Round-trip from

£442

Popular in

July

Cheapest in

February

Average price

£555
4/12-8/12
  • 4/12-8/12
  • 4 total stops
  • 36h 30m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£63 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 October 2025
Search Deals

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 31 October 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

Thu 4/12

06:50-18:25

2 stops17h 35m

Chicago O'Hare Intl

Mon 8/12

18:50-19:45

2 stops18h 55m

£442

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 10/12

07:10-17:20

2 stops16h 10m

Chicago O'Hare Intl

Wed 10/12

21:50-21:00

2 stops17h 10m

£904

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 21/12

07:10-17:55

2 stops16h 45m

Chicago O'Hare Intl

Mon 29/12

18:50-19:45

2 stops18h 55m

£907

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 3/12

07:10-17:20

2 stops16h 10m

Chicago O'Hare Intl

Wed 17/12

18:30-21:00

2 stops20h 30m

£922

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 23/12

07:35-17:55

2 stops16h 20m

Chicago O'Hare Intl

Sun 4/1

18:30-14:50

2 stops14h 20m

£961

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 1/12

07:15-15:10

1 stop13h 55m

Chicago O'Hare Intl

Thu 11/12

17:20-12:50

1 stop13h 30m

£983

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 23/12

07:35-17:55

2 stops16h 20m

Chicago O'Hare Intl

Sat 3/1

21:50-20:10

2 stops16h 20m

£1,075

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 29/11

07:15-14:20

1 stop13h 05m

Chicago O'Hare Intl

Sat 6/12

17:20-20:10

2 stops20h 50m

£1,207

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 20/12

07:15-17:20

2 stops16h 05m

Chicago O'Hare Intl

Sat 3/1

21:50-20:10

2 stops16h 20m

£1,406

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 9/1

07:35-19:15

2 stops17h 40m

£449

Flights are sorted by cheapest return flights first.

Deals found on 29/10

Showing 1-10 of 18 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.

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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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