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).

How far in advance should I book a flight from Chicago to London Southend Airport?

Travelers have found it’s best to book a flight 60 days in advance to save up to 11% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to London Southend Airport 1-2 weeks in advance for as low as $659, or $710 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to London Southend Airport?

Flights from Chicago to London Southend Airport lean towards being more expensive in June. Prices are generally better when you fly from Chicago to London Southend Airport in February, with the cheapest ticket starting at $472.

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.

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.

$284+ Cheap Flights from Chicago to London Southend Airport

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Chicago to Southend with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Southend

Round-trip from	$745 (Mytrip)
One-way from	$284 (Mytrip)
Popular in	June
Cheapest in	February
Average price	$659

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 ($208 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 September 2025

Search Deals

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 September 14, 2025.

Sat 11/227:15 amORD - SEN

2 stops31h 35mMultiple Airlines

Sun 11/303:15 pmSEN - ORD

2 stops31h 05mMultiple Airlines

Deal found 9/12

$745

Thu 10/210:40 amORD - SEN

2 stops23h 05mMultiple Airlines

Mon 10/611:05 amSEN - ORD

2 stops34h 50mMultiple Airlines

Deal found 9/12

$751

Tue 10/284:50 pmORD - SEN

2 stops21h 50mMultiple Airlines

Tue 11/47:35 amSEN - ORD

2 stops16h 20mMultiple Airlines

Deal found 9/12

$759

Thu 9/1810:40 amORD - SEN

2 stops23h 05mMultiple Airlines

Mon 9/2211:05 amSEN - ORD

2 stops14h 24mMultiple Airlines

Deal found 9/12

$1,134

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 September 14, 2025.

Sat 11/227:15 amORD - SEN

2 stops31h 35mMultiple Airlines

Sun 11/303:15 pmSEN - ORD

2 stops31h 05mMultiple Airlines

Deal found 9/12

$745

Thu 10/210:40 amORD - SEN

2 stops23h 05mMultiple Airlines

Mon 10/611:05 amSEN - ORD

2 stops34h 50mMultiple Airlines

Deal found 9/12

$751

Tue 10/284:50 pmORD - SEN

2 stops21h 50mMultiple Airlines

Tue 11/47:35 amSEN - ORD

2 stops16h 20mMultiple Airlines

Deal found 9/12

$759

Last-minute flights from Chicago to Southend
Discover last-minute flight deals from Chicago to Southend. Data last updated September 14, 2025 and is based on user searches.

Thu 9/1810:40 amORD - SEN

2 stops23h 05mMultiple Airlines

Mon 9/2211:05 amSEN - ORD

2 stops14h 24mMultiple Airlines

Deal found 9/12

$1,134

Thu 10/210:40 amORD - SEN

2 stops23h 05mMultiple Airlines

Mon 10/611:05 amSEN - ORD

2 stops34h 50mMultiple Airlines

Deal found 9/12

$751

Tue 10/284:50 pmORD - SEN

2 stops21h 50mMultiple Airlines

Tue 11/47:35 amSEN - ORD

2 stops16h 20mMultiple Airlines

Deal found 9/12

$759

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 September 14, 2025.

Sun 11/168:25 pmORD - SEN

3 stops20h 35mMultiple Airlines

Deal found 9/13

$284

Sun 10/56:00 pmORD - SEN

3 stops43h 50mMultiple Airlines

Deal found 9/13

$290

Sat 10/116:15 pmORD - SEN

3 stops35h 55mMultiple Airlines

Deal found 9/14

$306

Sun 10/196:00 pmORD - SEN

3 stops22h 25mMultiple Airlines

Deal found 9/12

$314

Sat 9/276:30 amORD - SEN

3 stops45h 55mMultiple Airlines

Deal found 9/12

$334

Thu 9/257:40 amORD - SEN

3 stops26h 05mMultiple Airlines

Deal found 9/12

$339

Tue 9/3011:13 amORD - SEN

3 stops29h 52mMultiple Airlines

Deal found 9/12

$356

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

Sat 11/22

7:15 am-8:50 pm

2 stops31h 35m

London Southend

Sun 11/30

3:15 pm-4:20 pm

2 stops31h 05m

$745

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Thu 10/2

10:40 am-3:45 pm

2 stops23h 05m

London Southend

Mon 10/6

11:05 am-3:55 pm

2 stops34h 50m

$751

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Tue 10/28

4:50 pm-7:40 pm

2 stops21h 50m

London Southend

Tue 11/4

7:35 am-5:55 pm

2 stops16h 20m

$759

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sun 11/16

8:25 pm-11:00 pm

3 stops20h 35m

$284

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sun 10/5

6:00 pm-7:50 pm

3 stops43h 50m

$290

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sat 10/11

6:15 pm-12:10 pm

3 stops35h 55m

$306

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sun 10/19

6:00 pm-10:25 pm

3 stops22h 25m

$314

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Sat 9/27

6:30 am-10:25 am

3 stops45h 55m

$334

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

Thu 9/25

7:40 am-3:45 pm

3 stops26h 05m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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

Hayes

Thornton Heath

Southend-on-Sea

Harrow

Canterbury

Croydon

Eastleigh

Dartford

Dover

Winchester

Orpington

Gatwick

Borehamwood

Aylesbury

Bedford

Wembley

Folkestone

Chichester

Arundel

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Southend

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$284+ 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 11/16. 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

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 September 14, 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 September 14, 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

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

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 September 14, 2025.