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$542+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This Mytrip deal was found by Cheapflights users on 11/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:30 amSEN - ORD
3 stops38h 55mMultiple Airlines
Sat 1/106:30 pmORD - SEN
3 stops20h 20mMultiple Airlines
Deal found 11/25$768
This Booking.com deal was found by Cheapflights users on 11/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:10 amSEN - ORD
2 stops16h 45mMultiple Airlines
Wed 12/173:50 pmORD - SEN
2 stops23h 10mMultiple Airlines
Deal found 11/24$910
This Mytrip deal was found by Cheapflights users on 11/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:30 amSEN - ORD
3 stops38h 55mMultiple Airlines
Tue 12/306:30 pmORD - SEN
3 stops22h 35mMultiple Airlines
Deal found 11/26$939
This Booking.com deal was found by Cheapflights users on 11/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:15 amSEN - ORD
3 stops38h 10mMultiple Airlines
Wed 12/106:30 pmORD - SEN
3 stops16h 45mMultiple Airlines
Deal found 11/23$945
This Booking.com deal was found by Cheapflights users on 11/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:15 amSEN - ORD
2 stops16h 05mMultiple Airlines
Wed 12/106:30 pmORD - SEN
2 stops16h 45mMultiple Airlines
Deal found 11/25$1,020
This Booking.com deal was found by Cheapflights users on 11/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:10 amSEN - ORD
2 stops16h 10mMultiple Airlines
Wed 1/76:30 pmORD - SEN
3 stops16h 45mMultiple Airlines
Deal found 11/24$1,106
This Mytrip deal was found by Cheapflights users on 11/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:10 amSEN - ORD
1 stop14h 00mMultiple Airlines
Thu 1/15:20 pmORD - SEN
1 stop13h 30mMultiple Airlines
Deal found 11/24$1,231
This Mytrip deal was found by Cheapflights users on 11/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:40 amSEN - ORD
1 stop13h 40mMultiple Airlines
Fri 1/24:25 pmORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 11/24$1,237
This Booking.com deal was found by Cheapflights users on 11/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:50 amSEN - ORD
3 stops38h 35mMultiple Airlines
Sun 12/217:40 pmORD - SEN
3 stops21h 20mMultiple Airlines
Deal found 11/26$1,261
This Booking.com deal was found by Cheapflights users on 11/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:15 amSEN - ORD
1 stop13h 05mMultiple Airlines
Wed 1/75:20 pmORD - SEN
2 stops17h 55mMultiple Airlines
Deal found 11/26$1,408
This Booking.com deal was found by Cheapflights users on 11/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:40 amSEN - ORD
2 stops33h 25mMultiple Airlines
Sat 1/34:20 pmORD - SEN
2 stops22h 30mMultiple Airlines
Deal found 11/24$1,417

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 November 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$768
(Mytrip)

One-way from

$542
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$629
Provider with most accurate pricing for London (LON)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for London (LON)-Chicago (CHI) flights.
Search Deals
From London Southend to Chicago (CHI)
Search Deals
One-way flight from London Southend to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 26, 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 12/11

6:30 am-3:25 pm

3 stops38h 55m

Chicago O'Hare Intl

Sat 1/10

6:30 pm-8:50 pm

3 stops20h 20m

$768

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 12/10

7:10 am-5:55 pm

2 stops16h 45m

Chicago O'Hare Intl

Wed 12/17

3:50 pm-9:00 pm

2 stops23h 10m

$910

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 12/18

6:30 am-3:25 pm

3 stops38h 55m

Chicago O'Hare Intl

Tue 12/30

6:30 pm-11:05 pm

3 stops22h 35m

$939

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 12/4

7:15 am-3:25 pm

3 stops38h 10m

Chicago O'Hare Intl

Wed 12/10

6:30 pm-5:15 pm

3 stops16h 45m

$945

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 12/6

7:15 am-5:20 pm

2 stops16h 05m

Chicago O'Hare Intl

Wed 12/10

6:30 pm-5:15 pm

2 stops16h 45m

$1,020

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 2/16

7:15 am-7:15 pm

2 stops18h 00m

Chicago O'Hare Intl

Thu 2/19

12:50 pm-12:50 pm

2 stops18h 00m

$1,095

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 12/17

7:10 am-5:20 pm

2 stops16h 10m

Chicago O'Hare Intl

Wed 1/7

6:30 pm-5:15 pm

3 stops16h 45m

$1,106

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 12/24

7:10 am-3:10 pm

1 stop14h 00m

Chicago O'Hare Intl

Thu 1/1

5:20 pm-12:50 pm

1 stop13h 30m

$1,231

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 12/26

6:40 am-2:20 pm

1 stop13h 40m

Chicago O'Hare Intl

Fri 1/2

4:25 pm-10:00 am

1 stop11h 35m

$1,237

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 12/11

6:50 am-3:25 pm

3 stops38h 35m

Chicago O'Hare Intl

Sun 12/21

7:40 pm-11:00 pm

3 stops21h 20m

$1,261

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 19 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 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.

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