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Cheap flights from London Southend Airport to Chicago from £368

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 15/6. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
18 Feb — 25 Feb1
1 adult
1 adult, Economy, 0 bags

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 19 January 2026.

Round-trip from

£560

One-way from

£368

Popular in

July

Cheapest in

February

Average price

£466
17/2-24/2
  • 17/2-24/2
  • 5 total stops
  • 47h 15m total
  • London to Chicago
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15/6
  • 15/6
  • 3 total stops
  • 40h 20m total
  • London to Chicago
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Highest demand for flights based on searches. 14% potential increase in price (£66 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
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Average for round-trip flights in January 2026
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Find flight deals from Southend to Chicago

Enter your travel dates to find the best prices.

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 19 January 2026.

Tue 17/220:20
SEN
-
ORD
2 stops24h 40m
Multiple Airlines
Tue 24/218:30
ORD
-
SEN
3 stops22h 35m
Multiple Airlines
Deal found 18/1£560
Tue 3/207:00
SEN
-
ORD
3 stops38h 00m
Multiple Airlines
Tue 10/218:30
ORD
-
SEN
3 stops22h 35m
Multiple Airlines
Deal found 18/1£625

Cheapflights Fare Finder

 
Customise 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 858,174 searches. Data last updated 19 January 2026.
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

Tue 17/2

20:20-15:00

2 stops24h 40m

Chicago O'Hare Intl

Tue 24/2

18:30-23:05

3 stops22h 35m

£560

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 3/2

07:00-15:00

3 stops38h 00m

Chicago O'Hare Intl

Tue 10/2

18:30-23:05

3 stops22h 35m

£625

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 15/6

07:30-17:50

3 stops40h 20m

£368

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 30/3

07:30-19:15

2 stops41h 45m

£389

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 4/3

07:10-17:20

2 stops16h 10m

£426

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 12/2

06:50-15:00

3 stops38h 10m

£442

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 12/6

22:00-17:50

3 stops25h 50m

£450

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 26/1

07:20-17:20

2 stops16h 00m

£451

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 27/1

07:00-10:05

2 stops33h 05m

£510

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 18/7

17:20-16:00

3 stops28h 40m

£527

Flights are sorted by cheapest return flights first.

Deals found on 16/1

Showing 1-10 of 12 results
1
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 return 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 holiday 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.

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Southend to Chicago

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Fly with Cheapflights

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How does Cheapflights help users find flights from Southend to Chicago?

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Can Cheapflights find flights from Southend to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Southend to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Southend to Chicago become cheaper?

Yes! Start tracking prices for Southend to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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