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Cheap flights from London Southend Airport to Chicago from £359

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
3 Feb — 10 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap 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 4 January 2026.

Fri 16/106:40SEN - ORD
2 stops16h 40mMultiple Airlines
Sun 18/118:30ORD - SEN
2 stops14h 20mMultiple Airlines
Deal found 2/1£684
Wed 13/515:40SEN - ORD
2 stops28h 35mMultiple Airlines
Sun 17/517:10ORD - SEN
1 stop11h 25mMultiple Airlines
Deal found 3/1£862
Mon 16/207:20SEN - ORD
2 stops41h 55mMultiple Airlines
Mon 23/216:25ORD - SEN
1 stop11h 55mMultiple Airlines
Deal found 2/1£902
Thu 8/106:50SEN - ORD
3 stops45h 52mMultiple Airlines
Fri 16/117:20ORD - SEN
3 stops20h 00mMultiple Airlines
Deal found 3/1£995
Sat 3/113:25SEN - ORD
2 stops55h 30mMultiple Airlines
Sat 10/117:20ORD - SEN
1 stop21h 30mMultiple Airlines
Deal found 3/1£4,603

Find 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 4 January 2026.

Round-trip from

£684

One-way from

£359

Popular in

July

Cheapest in

February

Average price

£512
16/1-18/1
  • 16/1-18/1
  • 4 total stops
  • 31h 00m total
  • London to Chicago
Search Deals
12/4
  • 12/4
  • 3 total stops
  • 30h 45m 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 January 2026
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 4 January 2026.
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

Fri 16/1

06:40-17:20

2 stops16h 40m

Chicago O'Hare Intl

Sun 18/1

18:30-14:50

2 stops14h 20m

£684

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 13/5

15:40-14:15

2 stops28h 35m

Chicago O'Hare Intl

Sun 17/5

17:10-10:35

1 stop11h 25m

£862

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 16/2

07:20-19:15

2 stops41h 55m

Chicago O'Hare Intl

Mon 23/2

16:25-10:20

1 stop11h 55m

£902

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 12/4

17:30-18:15

3 stops30h 45m

£359

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 30/1

07:35-20:00

2 stops42h 25m

£373

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 13/3

07:35-21:00

2 stops42h 25m

£374

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 6/2

07:35-20:00

2 stops42h 25m

£374

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 18/6

20:40-19:15

3 stops28h 35m

£384

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 21/6

11:00-19:15

2 stops38h 15m

£390

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 15/5

20:40-14:15

2 stops23h 35m

£396

Flights are sorted by cheapest return flights first.

Deals found on 2/1

Showing 1-10 of 13 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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Why should you use Cheapflights to find cheap flight tickets 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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