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Cheap flights from London Southend Airport to Chicago from £387

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 19/9. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
29 Aug — 5 Sep1
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 30 July 2026.

Wed 26/812:15
SEN
-
ORD
2 stops30h 40m
Multiple Airlines
Thu 3/908:40
ORD
-
SEN
2 stops20h 05m
Multiple Airlines
Deal found 28/7£575
Wed 26/812:15
SEN
-
ORD
2 stops30h 20m
Multiple Airlines
Wed 2/911:05
ORD
-
SEN
2 stops19h 55m
Multiple Airlines
Deal found 29/7£589
Tue 8/920:25
SEN
-
ORD
2 stops25h 35m
Multiple Airlines
Tue 15/916:20
ORD
-
SEN
1 stop21h 20m
Multiple Airlines
Deal found 29/7£958
Wed 29/707:15
SEN
-
ORD
3 stops42h 35m
Multiple Airlines
Sun 2/817:10
ORD
-
SEN
1 stop11h 20m
Multiple Airlines
Deal found 27/7£1,209
Tue 28/706:30
SEN
-
ORD
3 stops38h 15m
Multiple Airlines
Thu 30/717:10
ORD
-
SEN
1 stop11h 35m
Multiple Airlines
Deal found 27/7£1,301
Sun 26/717:30
SEN
-
ORD
3 stops32h 20m
Multiple Airlines
Thu 30/717:10
ORD
-
SEN
1 stop11h 35m
Multiple Airlines
Deal found 26/7£1,328
Fri 11/911:20
SEN
-
ORD
1 stop33h 50m
Multiple Airlines
Fri 18/916:05
ORD
-
SEN
2 stops23h 40m
Multiple Airlines
Deal found 28/7£1,501
Wed 29/712:15
SEN
-
ORD
2 stops15h 10m
Multiple Airlines
Wed 5/816:50
ORD
-
SEN
2 stops17h 50m
Multiple Airlines
Deal found 28/7£1,769

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 30 July 2026.

Round-trip from

£575

One-way from

£387

Popular in

July

Cheapest in

February

Average price

£719
26/8-3/9
  • 26/8-3/9
  • 4 total stops
  • 50h 45m total
  • London to Chicago
Search Deals
29/8
  • 29/8
  • 2 total stops
  • 29h 10m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (£83 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 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 30 July 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

Wed 26/8

12:15-12:55

2 stops30h 40m

Chicago O'Hare Intl

Thu 3/9

08:40-10:45

2 stops20h 05m

£575

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 26/8

12:15-12:35

2 stops30h 20m

Chicago O'Hare Intl

Wed 2/9

11:05-13:00

2 stops19h 55m

£589
Fastest return journey

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 8/9

20:25-16:00

2 stops25h 35m

Chicago O'Hare Intl

Tue 15/9

16:20-19:40

1 stop21h 20m

£958
Cheapest one-way

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 19/9

16:50-21:25

3 stops34h 35m

£387

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 17/11

15:50-18:25

2 stops32h 35m

£393

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 7/10

08:25-12:40

2 stops34h 15m

£400

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 30/9

08:25-12:40

2 stops34h 15m

£406

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 1/11

15:55-17:20

2 stops31h 25m

£409

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 28/11

06:50-14:00

2 stops37h 10m

£412

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 3/12

19:10-17:20

3 stops28h 10m

£415

Flights are sorted by cheapest return flights first.

Deals found on 29/7

Showing 1-10 of 14 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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