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Southend

$366+ Cheap flights from Chicago (CHI) to Southend (SEN)

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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SEN
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Chicago to Southend

Cheapest flights from Chicago to Southend
Explore the most affordable flight options available from Chicago to Southend. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:30 pm
ORD
-
SEN
2 stops20h 30m
Multiple Airlines
Mon 3/27:15 am
SEN
-
ORD
2 stops16h 05m
Multiple Airlines
Deal found 2/2$621
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:30 pm
ORD
-
SEN
2 stops16h 45m
Multiple Airlines
Sun 2/225:25 pm
SEN
-
ORD
2 stops29h 55m
Multiple Airlines
Deal found 2/3$688
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:30 pm
ORD
-
SEN
2 stops16h 45m
Multiple Airlines
Sun 3/155:25 pm
SEN
-
ORD
2 stops29h 55m
Multiple Airlines
Deal found 2/1$701
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:25 pm
ORD
-
SEN
2 stops20h 00m
Multiple Airlines
Sun 4/195:30 pm
SEN
-
ORD
3 stops30h 45m
Multiple Airlines
Deal found 2/2$739
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:25 pm
ORD
-
SEN
2 stops22h 35m
Multiple Airlines
Wed 3/257:10 am
SEN
-
ORD
1 stop14h 00m
Multiple Airlines
Deal found 2/1$818
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/86:50 pm
ORD
-
SEN
3 stops22h 10m
Multiple Airlines
Thu 2/126:50 am
SEN
-
ORD
3 stops38h 10m
Multiple Airlines
Deal found 2/2$907
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:35 pm
ORD
-
SEN
2 stops16h 25m
Multiple Airlines
Wed 3/187:10 am
SEN
-
ORD
2 stops18h 55m
Multiple Airlines
Deal found 2/1$958
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/287:15 am
ORD
-
SEN
2 stops21h 10m
Multiple Airlines
Sun 4/57:25 am
SEN
-
ORD
2 stops17h 22m
Multiple Airlines
Deal found 2/3$1,034
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/205:25 pm
ORD
-
SEN
1 stop11h 35m
Multiple Airlines
Fri 3/276:40 am
SEN
-
ORD
1 stop13h 40m
Multiple Airlines
Deal found 2/3$1,296

Find flight deals from Chicago to Southend

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Southend (SEN). 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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$621
(Mytrip)

One-way from

$366
(Kiwi.com)

Popular in

June

Cheapest in

April

Average price

$658
Provider with most accurate pricing for Chicago (CHI)-London (LON) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-London (LON) flights.
Search Deals
From Chicago (CHI) to London Southend
Search Deals
One-way flight from Chicago (CHI) to London Southend
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($202 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Southend 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 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Chicago to London Southend Airport that are best for you.

Fly from

Chicago

Fly to

Southend

Route

Depart

Return

Price

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Wed 2/25

6:30 pm-9:00 pm

2 stops20h 30m

London Southend

Mon 3/2

7:15 am-5:20 pm

2 stops16h 05m

$621

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Wed 3/11

7:30 pm-5:15 pm

2 stops16h 45m

London Southend

Sun 3/15

5:25 pm-6:20 pm

2 stops29h 55m

$701

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Wed 3/18

5:25 pm-9:00 pm

2 stops22h 35m

London Southend

Wed 3/25

7:10 am-4:10 pm

1 stop14h 00m

$818

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Wed 3/11

11:35 pm-9:00 pm

2 stops16h 25m

London Southend

Wed 3/18

7:10 am-9:05 pm

2 stops18h 55m

$958

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sat 3/28

7:15 am-9:25 am

2 stops21h 10m

London Southend

Sun 4/5

7:25 am-6:47 pm

2 stops17h 22m

$1,034

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Fri 3/20

5:25 pm-10:00 am

1 stop11h 35m

London Southend

Fri 3/27

6:40 am-3:20 pm

1 stop13h 40m

$1,296

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Mon 2/16

6:40 am-10:00 am

2 stops45h 20m

$366

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Wed 3/25

7:30 pm-9:10 am

3 stops32h 40m

$374

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sun 7/19

9:00 pm-11:20 am

2 stops32h 20m

$376

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Wed 4/1

7:25 pm-1:00 pm

3 stops35h 35m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 15 results
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Best time to book a flight from Chicago to Southend

Have a flexible travel schedule? Discover the best time to fly to Southend from Chicago with our price prediction graph.
Estimated round-trip 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 Chicago to London Southend Airport
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 Chicago to Southend. 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 Chicago to Southend that include hotel bookings?

    Yes. In addition to deals on Chicago to Southend flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Southend?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Southend.

  • Can I find deals for business class flights from Chicago to Southend?

    Yes. Cheapflights offers flight deals from Chicago to Southend by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Traveling to a place near London Southend Airport?

Book flights to London Southend Airport if you plan to visit one of these locations
Ilford
Hounslow
Croydon
Southend-on-Sea
Harrow
Eastleigh
Gatwick
Dartford
Dover
Winchester
Orpington
Watford
Hayes
Borehamwood
Aylesbury
Chipping Norton
Horley
Kingston upon Thames
Eastbourne
Sutton

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