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 49 days in advance to save up to 5% 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 49 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 $714, or $714 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.

$357+ Flights from Chicago to London Southend Airport

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Cheap flight deals from Chicago to Southend

Round-trip from	$886 (Mytrip)
One-way from	$357 (Kiwi.com)
Popular in	June
Cheapest in	February
Average price	$1,034

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 ($207 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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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 juillet 3, 2025.

jeu. 8/78:40 amORD - SEN

2 stops19h 50mMultiple Airlines

dim. 8/173:55 pmSEN - ORD

2 stops26h 15mMultiple Airlines

Deal found 7/1

$886

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 juillet 3, 2025.

jeu. 8/78:40 amORD - SEN

2 stops19h 50mMultiple Airlines

dim. 8/173:55 pmSEN - ORD

2 stops26h 15mMultiple Airlines

Deal found 7/1

$886

Last-minute flights from Chicago to Southend
Discover last-minute flight deals from Chicago to Southend. Data last updated juillet 3, 2025 and is based on user searches.

jeu. 8/78:40 amORD - SEN

2 stops19h 50mMultiple Airlines

dim. 8/173:55 pmSEN - ORD

2 stops26h 15mMultiple Airlines

Deal found 7/1

$886

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 juillet 3, 2025.

jeu. 8/76:00 pmORD - SEN

3 stops32h 40mMultiple Airlines

Deal found 7/2

$357

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

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Price

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

jeu. 8/7

8:40 am-10:30 am

2 stops19h 50m

London Southend

dim. 8/17

3:55 pm-12:10 pm

2 stops26h 15m

$886

ChicagoLondon

ORD - SEN

ORDSEN

Chicago O'Hare Intl

jeu. 8/7

6:00 pm-8:40 am

3 stops32h 40m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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.

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

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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.

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$357+ 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 8/7. 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

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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 juillet 3, 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 juillet 3, 2025.

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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.

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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?

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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 juillet 3, 2025.