In terms of precipitation, rainfall in London Southend Airport ranges from 1.6 - 2.8 inches per month. January is typically the wettest month, when rainfall can reach 2.8 in. July is typically the driest time to visit London Southend Airport when rainfall is around 1.6 in.

If weather is an important factor for your trip to London Southend Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 62.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 39.2 F).

What is the cheapest time of day to fly from CHI to SEN?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to London Southend Airport as you normally would.

Most accurate provider : When it comes to deals on Chicago-London Southend Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-London Southend Airport flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Chicago-London Southend Airport flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago-London Southend Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-London Southend Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$342+ Cheap Flights from Chicago to London Southend Airport

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1. Tell us where you want to go

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Cheap flight deals from Chicago to Southend

Most accurate provider	Expedia 2 stars
Most trusted provider	Expedia 3 stars
Round-trip from	$715 (Mytrip)
One-way from	$342 (Kiwi.com)
Popular in	June
Cheapest in	February
Average price	$670

Provider with most accurate pricing for Chicago (CHI)-London Southend flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-London Southend flights.

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From Chicago (CHI) to London Southend

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One-way flight from Chicago (CHI) to London Southend

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Highest demand for flights based on searches. 21% potential increase in price ($202 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).

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Average for round-trip flights in October 2025

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Find 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 octobre 30, 2025.

mer. 12/310:35 pmORD - SEN

2 stops16h 25mMultiple Airlines

lun. 12/87:15 amSEN - ORD

2 stops18h 50mMultiple Airlines

Deal found 10/30

$715

dim. 11/96:30 pmORD - SEN

2 stops14h 20mMultiple Airlines

dim. 11/165:25 pmSEN - ORD

2 stops29h 55mMultiple Airlines

Deal found 10/29

$733

mer. 11/510:35 pmORD - SEN

2 stops16h 25mMultiple Airlines

mer. 11/127:10 amSEN - ORD

2 stops18h 55mMultiple Airlines

Deal found 10/29

$748

lun. 12/157:40 pmORD - SEN

2 stops18h 05mMultiple Airlines

jeu. 12/186:50 amSEN - ORD

2 stops17h 05mMultiple Airlines

Deal found 10/30

$919

jeu. 12/188:00 amORD - SEN

3 stops21h 40mMultiple Airlines

ven. 12/267:35 amSEN - ORD

2 stops18h 30mMultiple Airlines

Deal found 10/30

$1,095

lun. 12/86:50 pmORD - SEN

2 stops18h 55mMultiple Airlines

jeu. 12/186:50 amSEN - ORD

2 stops17h 05mMultiple Airlines

Deal found 10/29

$1,213

dim. 12/217:40 pmORD - SEN

2 stops13h 10mMultiple Airlines

sam. 12/277:15 amSEN - ORD

2 stops16h 40mMultiple Airlines

Deal found 10/29

$1,519

lun. 12/226:50 pmORD - SEN

2 stops18h 55mMultiple Airlines

jeu. 1/16:50 amSEN - ORD

2 stops19h 10mMultiple Airlines

Deal found 10/30

$1,588

dim. 12/213:50 pmORD - SEN

2 stops17h 00mMultiple Airlines

ven. 1/26:40 amSEN - ORD

2 stops17h 15mMultiple Airlines

Deal found 10/29

$1,834

Best flights from Chicago to Southend
Discover carefully curated flight deals from Chicago to Southend that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated octobre 30, 2025.

dim. 11/96:30 pmORD - SEN

2 stops14h 20mMultiple Airlines

dim. 11/165:25 pmSEN - ORD

2 stops29h 55mMultiple Airlines

Deal found 10/29

$733

mer. 11/510:35 pmORD - SEN

2 stops16h 25mMultiple Airlines

mer. 11/127:10 amSEN - ORD

2 stops18h 55mMultiple Airlines

Deal found 10/29

$748

jeu. 11/135:20 pmORD - SEN

1 stop13h 30mMultiple Airlines

lun. 11/177:15 amSEN - ORD

1 stop13h 55mMultiple Airlines

Deal found 10/28

$757

dim. 12/75:20 pmORD - SEN

1 stop11h 10mMultiple Airlines

lun. 12/225:30 pmSEN - ORD

3 stops30h 25mMultiple Airlines

Deal found 10/28

$1,157

lun. 12/86:50 pmORD - SEN

2 stops18h 55mMultiple Airlines

jeu. 12/186:50 amSEN - ORD

2 stops17h 05mMultiple Airlines

Deal found 10/29

$1,213

ven. 12/124:25 pmORD - SEN

1 stop11h 35mMultiple Airlines

ven. 12/196:40 amSEN - ORD

2 stops19h 51mMultiple Airlines

Deal found 10/28

$1,432

dim. 12/217:40 pmORD - SEN

2 stops13h 10mMultiple Airlines

sam. 12/277:15 amSEN - ORD

2 stops16h 40mMultiple Airlines

Deal found 10/29

$1,519

dim. 12/213:50 pmORD - SEN

2 stops17h 00mMultiple Airlines

ven. 1/26:40 amSEN - ORD

2 stops17h 15mMultiple Airlines

Deal found 10/29

$1,834

lun. 12/2912:55 pmORD - SEN

2 stops15h 20mMultiple Airlines

sam. 1/37:15 amSEN - ORD

1 stop13h 05mMultiple Airlines

Deal found 10/27

$3,251

Last-minute flights from Chicago to Southend
Discover last-minute flight deals from Chicago to Southend. Data last updated octobre 30, 2025 and is based on user searches.

mer. 11/510:35 pmORD - SEN

2 stops16h 25mMultiple Airlines

mer. 11/127:10 amSEN - ORD

2 stops18h 55mMultiple Airlines

Deal found 10/29

$748

dim. 11/96:30 pmORD - SEN

2 stops14h 20mMultiple Airlines

dim. 11/165:25 pmSEN - ORD

2 stops29h 55mMultiple Airlines

Deal found 10/29

$733

One-way flights from Chicago to Southend
Search for one-way flight options from Chicago to Southend. Find affordable one-way fares based on user searches. Data last updated octobre 30, 2025.

mer. 1/1412:05 pmORD - SEN

3 stops39h 05mMultiple Airlines

Deal found 10/30

$342

sam. 11/152:31 pmORD - SEN

3 stops38h 54mMultiple Airlines

Deal found 10/30

$351

jeu. 11/134:57 pmORD - SEN

3 stops38h 18mMultiple Airlines

Deal found 10/30

$355

jeu. 11/62:31 pmORD - SEN

3 stops40h 44mMultiple Airlines

Deal found 10/29

$364

sam. 11/223:26 pmORD - SEN

2 stops37h 04mMultiple Airlines

Deal found 10/30

$370

mar. 12/22:01 pmORD - SEN

3 stops26h 44mMultiple Airlines

Deal found 10/30

$391

mer. 11/2610:59 amORD - SEN

3 stops24h 16mMultiple Airlines

Deal found 10/30

$412

dim. 11/166:40 amORD - SEN

3 stops21h 50mMultiple Airlines

Deal found 10/29

$417

mer. 12/32:01 pmORD - SEN

3 stops21h 14mMultiple Airlines

Deal found 10/29

$425

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to London Southend Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

dim. 11/9

6:30 pm-2:50 pm

2 stops14h 20m

London Southend

dim. 11/16

5:25 pm-5:20 pm

2 stops29h 55m

$733

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

mer. 11/5

10:35 pm-9:00 pm

2 stops16h 25m

London Southend

mer. 11/12

7:10 am-8:05 pm

2 stops18h 55m

$748

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

jeu. 11/13

5:20 pm-12:50 pm

1 stop13h 30m

London Southend

lun. 11/17

7:15 am-3:10 pm

1 stop13h 55m

$757

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

dim. 12/7

5:20 pm-10:30 am

1 stop11h 10m

London Southend

lun. 12/22

5:30 pm-5:55 pm

3 stops30h 25m

$1,157

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

lun. 12/8

6:50 pm-7:45 pm

2 stops18h 55m

London Southend

jeu. 12/18

6:50 am-5:55 pm

2 stops17h 05m

$1,213

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

ven. 12/12

4:25 pm-10:00 am

1 stop11h 35m

London Southend

ven. 12/19

6:40 am-8:31 pm

2 stops19h 51m

$1,432

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

dim. 12/21

7:40 pm-2:50 pm

2 stops13h 10m

London Southend

sam. 12/27

7:15 am-5:55 pm

2 stops16h 40m

$1,519

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

dim. 12/21

3:50 pm-2:50 pm

2 stops17h 00m

London Southend

ven. 1/2

6:40 am-5:55 pm

2 stops17h 15m

$1,834

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

lun. 12/29

12:55 pm-10:15 am

2 stops15h 20m

London Southend

sam. 1/3

7:15 am-2:20 pm

1 stop13h 05m

$3,251

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

mer. 1/14

12:05 pm-9:10 am

3 stops39h 05m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 19 results

Most accurate provider: When it comes to deals on Chicago-London Southend Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-London Southend Airport flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Chicago-London Southend Airport flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Chicago-London Southend Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-London Southend Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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.

Hounslow

Ilford

Hayes

Southend-on-Sea

Harrow

Croydon

Eastleigh

Dartford

Dover

Winchester

Orpington

Gatwick

Borehamwood

Aylesbury

Bedford

Chipping Norton

Wembley

Folkestone

Eastbourne

Sutton

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$342+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Southend with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Southend

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chicago to Southend

Cheapest flights from Chicago to SouthendExplore 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 octobre 30, 2025.

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 octobre 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to London Southend Airport that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to London Southend Airport

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?

How can I find direct flights from Chicago to Southend?

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

Traveling to a place near London Southend Airport?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Southend

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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 octobre 30, 2025.