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Cheap flights from London Southend Airport to Chicago from £369

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
17 May — 24 May1
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 17 April 2026.

Wed 22/408:25
SEN
-
ORD
3 stops44h 42m
Multiple Airlines
Sat 25/416:20
ORD
-
SEN
3 stops25h 00m
Multiple Airlines
Deal found 13/4£680
Sun 20/917:30
SEN
-
ORD
3 stops31h 45m
Multiple Airlines
Sat 26/919:25
ORD
-
SEN
2 stops14h 15m
Multiple Airlines
Deal found 16/4£720
Sat 18/417:20
SEN
-
ORD
2 stops28h 40m
Multiple Airlines
Sat 25/416:20
ORD
-
SEN
3 stops25h 00m
Multiple Airlines
Deal found 13/4£832
Sun 31/507:25
SEN
-
ORD
2 stops52h 39m
Multiple Airlines
Sun 7/617:10
ORD
-
SEN
1 stop11h 20m
Multiple Airlines
Deal found 16/4£1,086
Fri 22/511:20
SEN
-
ORD
2 stops16h 00m
Multiple Airlines
Sat 30/517:10
ORD
-
SEN
1 stop11h 15m
Multiple Airlines
Deal found 15/4£1,094
Fri 15/514:30
SEN
-
ORD
2 stops30h 40m
Multiple Airlines
Wed 27/517:10
ORD
-
SEN
1 stop13h 50m
Multiple Airlines
Deal found 14/4£1,105
Thu 28/506:30
SEN
-
ORD
2 stops39h 30m
Multiple Airlines
Thu 4/616:20
ORD
-
SEN
1 stop21h 15m
Multiple Airlines
Deal found 13/4£1,501
Fri 22/514:30
SEN
-
ORD
2 stops35h 20m
Multiple Airlines
Tue 26/516:20
ORD
-
SEN
1 stop21h 20m
Multiple Airlines
Deal found 17/4£1,590
Fri 17/411:20
SEN
-
ORD
2 stops16h 05m
Multiple Airlines
Thu 23/413:06
ORD
-
SEN
2 stops15h 39m
Multiple Airlines
Deal found 16/4£1,726

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 17 April 2026.

Round-trip from

£720

One-way from

£369

Popular in

July

Cheapest in

September

Average price

£538
20/9-26/9
  • 20/9-26/9
  • 5 total stops
  • 46h 00m total
  • London to Chicago
Search Deals
9/10
  • 9/10
  • 2 total stops
  • 34h 45m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£50 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 April 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 17 April 2026.
Use the filters below to find and compare flights from London Southend Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 20/9

17:30-19:15

3 stops31h 45m

Chicago O'Hare Intl

Sat 26/9

19:25-15:40

2 stops14h 15m

£720

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 31/5

07:25-06:04

2 stops52h 39m

Chicago O'Hare Intl

Sun 7/6

17:10-10:30

1 stop11h 20m

£1,086
Fastest return journey

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 22/5

11:20-21:20

2 stops16h 00m

Chicago O'Hare Intl

Sat 30/5

17:10-10:25

1 stop11h 15m

£1,094

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 15/5

14:30-15:10

2 stops30h 40m

Chicago O'Hare Intl

Wed 27/5

17:10-13:00

1 stop13h 50m

£1,105

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 28/5

06:30-16:00

2 stops39h 30m

Chicago O'Hare Intl

Thu 4/6

16:20-19:35

1 stop21h 15m

£1,501

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 22/5

14:30-19:50

2 stops35h 20m

Chicago O'Hare Intl

Tue 26/5

16:20-19:40

1 stop21h 20m

£1,590
Cheapest one-way

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 12/5

06:30-16:00

2 stops39h 30m

£376

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 4/5

11:10-15:03

3 stops33h 53m

£382

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 4/6

17:15-17:50

3 stops30h 35m

£394

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 13/6

07:55-11:50

2 stops33h 55m

£395

Flights are sorted by cheapest return flights first.

Deals found on 13/4

Showing 1-10 of 18 resultsSorted by cheapest first
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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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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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