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$550+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Southend to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Southend (SEN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 3, 2025.

Round-trip from

$1,121
(Kiwi.com)

One-way from

$550
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$880
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. 12% potential increase in price ($100 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 July 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 July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:40 pmSEN - ORD
2 stops42h 00mMultiple Airlines
Thu 8/285:10 pmORD - SEN
1 stop11h 20mMultiple Airlines
Deal found 7/1$1,121

Cheapflights Fare Finder

Customize your flight search to find flights from Southend to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
Use the filters below to find and compare flights from London Southend Airport to Chicago that are best for you.

Fly from

Southend

Fly to

Chicago

Route

Depart

Return

Price

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 8/21

5:40 pm-5:40 am

2 stops42h 00m

Chicago O'Hare Intl

Thu 8/28

5:10 pm-10:30 am

1 stop11h 20m

$1,121

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 10/5

5:30 pm-4:10 pm

2 stops28h 40m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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

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?

    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.

See more FAQs

Traveling to a place near London Southend Airport?

Book flights to London Southend Airport if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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