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Cheap flights from London Southend Airport to Chicago from £410

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
1 Jan — 8 Jan1
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 2 Dezember 2025.

Fr 19/1216:50SEN - ORD
3 stops30h 15mMultiple Airlines
Mi 7/118:30ORD - SEN
3 stops16h 45mMultiple Airlines
Deal found 30/11£777
Mi 3/1207:10SEN - ORD
2 stops16h 45mMultiple Airlines
Mi 17/1219:40ORD - SEN
2 stops19h 20mMultiple Airlines
Deal found 30/11£831
So 21/1207:10SEN - ORD
3 stops41h 15mMultiple Airlines
Sa 3/118:30ORD - SEN
2 stops20h 20mMultiple Airlines
Deal found 1/12£1,003
Mi 10/1207:10SEN - ORD
2 stops19h 00mMultiple Airlines
Mi 17/1215:50ORD - SEN
3 stops24h 35mMultiple Airlines
Deal found 30/11£1,015
Sa 20/1207:15SEN - ORD
1 stop13h 05mMultiple Airlines
Sa 27/1217:20ORD - SEN
2 stops20h 50mMultiple Airlines
Deal found 30/11£1,237
Di 9/1207:35SEN - ORD
2 stops15h 45mMultiple Airlines
Mi 17/1217:20ORD - SEN
2 stops17h 55mMultiple Airlines
Deal found 30/11£1,261
Mo 1/1207:15SEN - ORD
1 stop13h 55mMultiple Airlines
Di 2/1210:36ORD - SEN
2 stops17h 24mMultiple Airlines
Deal found 30/11£1,647
Mo 1/1207:15SEN - ORD
1 stop13h 55mMultiple Airlines
Mi 3/1222:35ORD - SEN
2 stops16h 25mMultiple Airlines
Deal found 30/11£1,698
Sa 13/1207:15SEN - ORD
2 stops16h 40mMultiple Airlines
Fr 26/1216:25ORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 1/12£1,776

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 2 Dezember 2025.

Round-trip from

£699

One-way from

£410

Popular in

July

Cheapest in

February

Average price

£604
15/1-22/1
  • 15/1-22/1
  • 3 total stops
  • 55h 04m total
  • London to Chicago
Search Deals
5/4
  • 5/4
  • 3 total stops
  • 36h 50m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£60 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£9 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 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 2 Dezember 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

Do 15/1

06:50-18:24

2 stops41h 34m

Chicago O'Hare Intl

Do 22/1

17:20-12:50

1 stop13h 30m

£699

LondonChicago

SEN - ORD

SENORD

London Southend

Fr 19/12

16:50-17:05

3 stops30h 15m

Chicago O'Hare Intl

Mi 7/1

18:30-17:15

3 stops16h 45m

£777

LondonChicago

SEN - ORD

SENORD

London Southend

Mo 5/1

07:15-19:15

2 stops18h 00m

Chicago O'Hare Intl

Sa 10/1

21:00-20:50

2 stops17h 50m

£794

LondonChicago

SEN - ORD

SENORD

London Southend

So 21/12

07:10-18:25

3 stops41h 15m

Chicago O'Hare Intl

Sa 3/1

18:30-20:50

2 stops20h 20m

£1,003

LondonChicago

SEN - ORD

SENORD

London Southend

Mi 14/1

15:35-10:05

2 stops48h 30m

Chicago O'Hare Intl

Mi 21/1

16:25-17:15

1 stop18h 50m

£1,114

LondonChicago

SEN - ORD

SENORD

London Southend

Sa 20/12

07:15-14:20

1 stop13h 05m

Chicago O'Hare Intl

Sa 27/12

17:20-20:10

2 stops20h 50m

£1,237

LondonChicago

SEN - ORD

SENORD

London Southend

Sa 13/12

07:15-17:55

2 stops16h 40m

Chicago O'Hare Intl

Fr 26/12

16:25-10:00

1 stop11h 35m

£1,776

LondonChicago

SEN - ORD

SENORD

London Southend

Do 11/12

18:05-14:57

2 stops50h 52m

£423

LondonChicago

SEN - ORD

SENORD

London Southend

Di 23/12

20:20-17:20

3 stops27h 00m

£439

LondonChicago

SEN - ORD

SENORD

London Southend

So 29/3

07:25-23:33

2 stops22h 08m

£439

Flights are sorted by cheapest return flights first.

Deals found on 1/12

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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Alternative routes for Southend to Chicago

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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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