What is the cheapest month to book a flight from London Southend Airport to Chicago?

Currently, August is the cheapest month in which you can book a flight from London Southend Airport to Chicago (average of $245). Flying from London Southend Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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

When flying from London Southend Airport to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 vacation 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.

$541+ Flights from London Southend Airport to Chicago

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Cheap flight deals from Southend to Chicago

Round-trip from	$958 (Kiwi.com)
One-way from	$541 (Kiwi.com)
Popular in	July
Cheapest in	February
Average price	$593

From London Southend to Chicago (CHI)

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

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Highest demand for flights based on searches. 14% potential increase in price ($113 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Find flight deals from Southend to Chicago

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 September 17, 2025.

Thu 10/307:15 amSEN - ORD

2 stops38h 00mMultiple Airlines

Thu 11/65:20 pmORD - SEN

1 stop14h 15mMultiple Airlines

Deal found 9/15

$958

Sat 11/18:40 amSEN - ORD

2 stops36h 05mMultiple Airlines

Sat 11/85:20 pmORD - SEN

1 stop21h 30mMultiple Airlines

Deal found 9/16

$963

Sat 12/207:15 amSEN - ORD

1 stop13h 05mMultiple Airlines

Sat 12/275:20 pmORD - SEN

2 stops20h 50mMultiple Airlines

Deal found 9/15

$1,286

Best flights from Southend to Chicago
Discover carefully curated flight deals from Southend to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2025.

Thu 10/307:15 amSEN - ORD

2 stops38h 00mMultiple Airlines

Thu 11/65:20 pmORD - SEN

1 stop14h 15mMultiple Airlines

Deal found 9/15

$958

Sat 11/18:40 amSEN - ORD

2 stops36h 05mMultiple Airlines

Sat 11/85:20 pmORD - SEN

1 stop21h 30mMultiple Airlines

Deal found 9/16

$963

Sat 12/207:15 amSEN - ORD

1 stop13h 05mMultiple Airlines

Sat 12/275:20 pmORD - SEN

2 stops20h 50mMultiple Airlines

Deal found 9/15

$1,286

Last-minute flights from Southend to Chicago
Discover last-minute flight deals from Southend to Chicago. Data last updated September 17, 2025 and is based on user searches.

Thu 10/307:15 amSEN - ORD

2 stops38h 00mMultiple Airlines

Thu 11/65:20 pmORD - SEN

1 stop14h 15mMultiple Airlines

Deal found 9/15

$958

One-way flights from Southend to Chicago
Search for one-way flight options from Southend to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2025.

Mon 10/208:05 pmSEN - ORD

3 stops46h 40mMultiple Airlines

Deal found 9/17

$541

Sat 10/255:30 pmSEN - ORD

3 stops28h 15mMultiple Airlines

Deal found 9/17

$544

Sun 11/303:15 pmSEN - ORD

3 stops32h 40mMultiple Airlines

Deal found 9/16

$545

Mon 12/87:15 amSEN - ORD

2 stops16h 40mMultiple Airlines

Deal found 9/15

$546

Thu 9/256:30 amSEN - ORD

2 stops40h 00mMultiple Airlines

Deal found 9/16

$548

Mon 9/228:05 pmSEN - ORD

3 stops43h 13mMultiple Airlines

Deal found 9/16

$562

Mon 10/611:05 amSEN - ORD

3 stops28h 38mMultiple Airlines

Deal found 9/16

$576

Mon 11/37:30 amSEN - ORD

2 stops16h 25mMultiple Airlines

Deal found 9/15

$588

Cheapflights Fare Finder

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

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 10/30

7:15 am-4:15 pm

2 stops38h 00m

Chicago O'Hare Intl

Thu 11/6

5:20 pm-1:35 pm

1 stop14h 15m

$958

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 11/1

8:40 am-3:45 pm

2 stops36h 05m

Chicago O'Hare Intl

Sat 11/8

5:20 pm-8:50 pm

1 stop21h 30m

$963

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 12/20

7:15 am-2:20 pm

1 stop13h 05m

Chicago O'Hare Intl

Sat 12/27

5:20 pm-8:10 pm

2 stops20h 50m

$1,286

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 10/20

8:05 pm-12:45 pm

3 stops46h 40m

$541

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 10/25

5:30 pm-3:45 pm

3 stops28h 15m

$544

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 12/8

7:15 am-5:55 pm

2 stops16h 40m

$546

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 9/25

6:30 am-4:30 pm

2 stops40h 00m

$548

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 9/22

8:05 pm-9:18 am

3 stops43h 13m

$562

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 9/21

3:35 pm-4:40 pm

2 stops31h 05m

$574

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 10/6

11:05 am-9:43 am

3 stops28h 38m

$576

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 12 results

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 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 London Southend Airport to Chicago

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 Southend to Chicago that include hotel bookings?
Yes. In addition to deals on Southend to Chicago flights, Cheapflights offers vacation 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.
What is the cheapest month to book a flight from London Southend Airport to Chicago?
Currently, August is the cheapest month in which you can book a flight from London Southend Airport to Chicago (average of $245). Flying from London Southend Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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$541+ Cheap flights from Southend (SEN) to Chicago (CHI)

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Southend to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Southend to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Southend to Chicago

Cheapest flights from Southend to ChicagoExplore 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 September 17, 2025.

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 September 17, 2025.

Cheapflights Fare Finder

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

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.

Cheapflights Insights

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

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?

How can I find direct flights from Southend to Chicago?

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

What is the cheapest month to book a flight from London Southend Airport to Chicago?

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

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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 September 17, 2025.