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).

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

To save up to 31% on this flight, we recommend booking at least 56 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from London Southend Airport to Chicago from $664 1-2 weeks out and tickets from $901 for flights departing within the next 72 hours.

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

February can be a great time to fly to Chicago from London Southend Airport with a flight ticket averaging about $697. Cheapflights users have found deals in the month of February for as cheap as $428. The most expensive prices can be found in the month of July.

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.

$589+ Flights from London Southend Airport to Chicago

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Cheap flight deals from Southend to Chicago

Round-trip from	$1,308 (Booking.com)
One-way from	$600 (Kiwi.com)
Popular in	July
Cheapest in	February
Average price	$843

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. 13% potential increase in price ($113 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).

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Average for round-trip flights in August 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 August 18, 2025.

Mon 9/111:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Thu 9/45:10 pmORD - SEN

1 stop16h 35mMultiple Airlines

Deal found 8/16

$1,308

Tue 9/307:00 amSEN - ORD

2 stops32h 40mMultiple Airlines

Tue 10/74:15 pmORD - SEN

1 stop21h 25mMultiple Airlines

Deal found 8/16

$1,487

Mon 8/2511:30 amSEN - ORD

2 stops15h 45mMultiple Airlines

Wed 8/279:15 pmORD - SEN

2 stops17h 35mMultiple Airlines

Deal found 8/16

$1,540

Fri 8/2211:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Wed 8/279:15 pmORD - SEN

2 stops17h 35mMultiple Airlines

Deal found 8/18

$1,625

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 August 18, 2025.

Mon 9/111:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Thu 9/45:10 pmORD - SEN

1 stop16h 35mMultiple Airlines

Deal found 8/16

$1,308

Tue 9/307:00 amSEN - ORD

2 stops32h 40mMultiple Airlines

Tue 10/74:15 pmORD - SEN

1 stop21h 25mMultiple Airlines

Deal found 8/16

$1,487

Mon 8/2511:30 amSEN - ORD

2 stops15h 45mMultiple Airlines

Wed 8/279:15 pmORD - SEN

2 stops17h 35mMultiple Airlines

Deal found 8/16

$1,540

Fri 8/2211:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Wed 8/279:15 pmORD - SEN

2 stops17h 35mMultiple Airlines

Deal found 8/18

$1,625

Last-minute flights from Southend to Chicago
Discover last-minute flight deals from Southend to Chicago. Data last updated August 18, 2025 and is based on user searches.

Fri 8/2211:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Wed 8/279:15 pmORD - SEN

2 stops17h 35mMultiple Airlines

Deal found 8/18

$1,625

Mon 8/2511:30 amSEN - ORD

2 stops15h 45mMultiple Airlines

Wed 8/279:15 pmORD - SEN

2 stops17h 35mMultiple Airlines

Deal found 8/16

$1,540

Mon 9/111:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Thu 9/45:10 pmORD - SEN

1 stop16h 35mMultiple Airlines

Deal found 8/16

$1,308

Tue 9/307:00 amSEN - ORD

2 stops32h 40mMultiple Airlines

Tue 10/74:15 pmORD - SEN

1 stop21h 25mMultiple Airlines

Deal found 8/16

$1,487

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 August 18, 2025.

Thu 9/255:40 pmSEN - ORD

2 stops26h 20mMultiple Airlines

Deal found 8/16

$600

Wed 9/243:40 pmSEN - ORD

2 stops26h 55mMultiple Airlines

Deal found 8/16

$689

Tue 9/238:25 pmSEN - ORD

3 stops46h 10mMultiple Airlines

Deal found 8/16

$692

Mon 11/107:15 amSEN - ORD

2 stops16h 05mMultiple Airlines

Deal found 8/18

$698

Sun 10/123:35 pmSEN - ORD

2 stops28h 25mMultiple Airlines

Deal found 8/16

$703

Fri 8/221:35 pmSEN - ORD

2 stops32h 55mMultiple Airlines

Deal found 8/17

$724

Mon 9/111:05 amSEN - ORD

2 stops16h 10mMultiple Airlines

Deal found 8/15

$746

Mon 8/2511:30 amSEN - ORD

2 stops15h 45mMultiple Airlines

Deal found 8/17

$835

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

Mon 9/1

11:05 am-9:15 pm

2 stops16h 10m

Chicago O'Hare Intl

Thu 9/4

5:10 pm-3:45 pm

1 stop16h 35m

$1,308

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 9/30

7:00 am-9:40 am

2 stops32h 40m

Chicago O'Hare Intl

Tue 10/7

4:15 pm-7:40 pm

1 stop21h 25m

$1,487

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 8/25

11:30 am-9:15 pm

2 stops15h 45m

Chicago O'Hare Intl

Wed 8/27

9:15 pm-8:50 pm

2 stops17h 35m

$1,540

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 8/22

11:05 am-9:15 pm

2 stops16h 10m

Chicago O'Hare Intl

Wed 8/27

9:15 pm-8:50 pm

2 stops17h 35m

$1,625

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 8/29

1:35 pm-4:30 pm

3 stops32h 55m

$589

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 11/17

7:15 am-10:05 am

3 stops32h 50m

$599

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 9/25

5:40 pm-2:00 pm

2 stops26h 20m

$600

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 2/9

7:15 am-5:20 pm

2 stops16h 05m

$607

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 12/30

8:20 pm-3:00 pm

2 stops24h 40m

$611

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 1/16

7:35 am-5:20 pm

2 stops15h 45m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 15 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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$589+ 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 8/29. 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 August 18, 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 August 18, 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?

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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 August 18, 2025.