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Cheap flights from London Southend Airport to Chicago from £408

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
23 Jan — 30 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Southend to Chicago

Enter your travel dates to find the best prices.

Best flights from Southend to Chicago
Discover carefully curated flight deals from Southend to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 24 December 2025.

Wed 4/207:10SEN - ORD
2 stops15h 35mMultiple Airlines
Wed 11/219:20ORD - SEN
3 stops19h 40mMultiple Airlines
Deal found 21/12£527
Fri 6/206:40SEN - ORD
1 stop13h 40mMultiple Airlines
Fri 13/216:25ORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 23/12£893
Thu 5/214:35SEN - ORD
1 stop29h 45mMultiple Airlines
Thu 12/219:20ORD - SEN
2 stops37h 45mMultiple Airlines
Deal found 21/12£1,733

Find 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 24 December 2025.

Round-trip from

£527

One-way from

£408

Popular in

July

Cheapest in

February

Average price

£592
4/2-11/2
  • 4/2-11/2
  • 5 total stops
  • 35h 15m total
  • London to Chicago
Search Deals
11/1
  • 11/1
  • 3 total stops
  • 45h 32m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£59 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£9 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 24 December 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

Wed 4/2

07:10-16:45

2 stops15h 35m

Chicago O'Hare Intl

Wed 11/2

19:20-21:00

3 stops19h 40m

£527

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 6/2

06:40-14:20

1 stop13h 40m

Chicago O'Hare Intl

Fri 13/2

16:25-10:00

1 stop11h 35m

£893

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 5/2

14:35-14:20

1 stop29h 45m

Chicago O'Hare Intl

Thu 12/2

19:20-15:05

2 stops37h 45m

£1,733

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 11/1

07:10-22:42

3 stops45h 32m

£408

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 30/3

07:30-14:15

2 stops36h 45m

£417

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 12/6

07:30-15:10

3 stops37h 40m

£425

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 22/3

07:10-08:13

3 stops30h 03m

£429

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 10/4

11:20-21:40

2 stops16h 20m

£436

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 16/1

07:35-17:20

2 stops15h 45m

£438

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 21/3

20:00-21:00

2 stops30h 00m

£453

Flights are sorted by cheapest return flights first.

Deals found on 22/12

Showing 1-10 of 14 results
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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.

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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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Why should you use Cheapflights to find cheap flight tickets from Southend to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Southend to Chicago for you. Better yet — we are completely free to use.

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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