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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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 18, 2025.

This Mytrip deal was found by Cheapflights users on 11/18. 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.
Tue 12/28:00 amSEN - ORD
3 stops37h 00mMultiple Airlines
Tue 12/96:30 pmORD - SEN
3 stops22h 35mMultiple Airlines
Deal found 11/18$722
This Mytrip deal was found by Cheapflights users on 11/17. 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.
Sat 11/226:30 amSEN - ORD
3 stops38h 15mMultiple Airlines
Sun 12/76:30 pmORD - SEN
3 stops22h 30mMultiple Airlines
Deal found 11/17$732
This Booking.com deal was found by Cheapflights users on 11/17. 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 11/276:50 amSEN - ORD
3 stops38h 10mMultiple Airlines
Sun 11/306:30 pmORD - SEN
3 stops22h 30mMultiple Airlines
Deal found 11/17$1,006
This Mytrip deal was found by Cheapflights users on 11/17. 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 11/197:10 amSEN - ORD
2 stops16h 10mMultiple Airlines
Sat 11/296:30 pmORD - SEN
2 stops20h 20mMultiple Airlines
Deal found 11/17$1,129
This Mytrip deal was found by Cheapflights users on 11/17. 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.
Tue 12/238:20 pmSEN - ORD
2 stops24h 40mMultiple Airlines
Tue 12/3012:50 pmORD - SEN
2 stops15h 10mMultiple Airlines
Deal found 11/17$1,197
This Booking.com deal was found by Cheapflights users on 11/16. 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.
Mon 11/177:15 amSEN - ORD
2 stops16h 05mMultiple Airlines
Tue 11/1810:35 amORD - SEN
2 stops17h 25mMultiple Airlines
Deal found 11/16$1,308
This Booking.com deal was found by Cheapflights users on 11/17. 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.
Fri 12/196:40 amSEN - ORD
1 stop13h 40mMultiple Airlines
Sun 1/44:25 pmORD - SEN
1 stop16h 25mMultiple Airlines
Deal found 11/17$1,440
This Booking.com deal was found by Cheapflights users on 11/17. 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 12/186:30 amSEN - ORD
3 stops38h 55mMultiple Airlines
Fri 1/24:25 pmORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 11/17$1,450
This Booking.com deal was found by Cheapflights users on 11/18. 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.
Tue 12/237:35 amSEN - ORD
2 stops15h 45mMultiple Airlines
Sun 1/46:30 pmORD - SEN
2 stops14h 20mMultiple Airlines
Deal found 11/18$1,483
This Mytrip deal was found by Cheapflights users on 11/17. 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.
Sat 12/207:15 amSEN - ORD
1 stop13h 05mMultiple Airlines
Fri 1/24:25 pmORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 11/17$1,654
This Mytrip deal was found by Cheapflights users on 11/17. 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.
Sat 12/207:15 amSEN - ORD
2 stops16h 05mMultiple Airlines
Sun 12/286:30 pmORD - SEN
2 stops14h 20mMultiple Airlines
Deal found 11/17$1,688
This Booking.com deal was found by Cheapflights users on 11/17. 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.
Fri 12/196:40 amSEN - ORD
2 stops16h 40mMultiple Airlines
Fri 1/24:25 pmORD - SEN
1 stop11h 35mMultiple Airlines
Deal found 11/17$2,114

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 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$722
(Mytrip)

One-way from

$550
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$619
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 ($106 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 18, 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

Tue 12/2

8:00 am-3:00 pm

3 stops37h 00m

Chicago O'Hare Intl

Tue 12/9

6:30 pm-11:05 pm

3 stops22h 35m

$722

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 3/8

7:10 am-9:43 pm

3 stops44h 33m

Chicago O'Hare Intl

Sun 3/15

7:30 pm-11:00 pm

3 stops22h 30m

$773

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 12/23

8:20 pm-3:00 pm

2 stops24h 40m

Chicago O'Hare Intl

Tue 12/30

12:50 pm-10:00 am

2 stops15h 10m

$1,197

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 12/19

6:40 am-2:20 pm

1 stop13h 40m

Chicago O'Hare Intl

Sun 1/4

4:25 pm-2:50 pm

1 stop16h 25m

$1,440

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 12/18

6:30 am-3:25 pm

3 stops38h 55m

Chicago O'Hare Intl

Fri 1/2

4:25 pm-10:00 am

1 stop11h 35m

$1,450

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 12/23

7:35 am-5:20 pm

2 stops15h 45m

Chicago O'Hare Intl

Sun 1/4

6:30 pm-2:50 pm

2 stops14h 20m

$1,483

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 12/20

7:15 am-2:20 pm

1 stop13h 05m

Chicago O'Hare Intl

Fri 1/2

4:25 pm-10:00 am

1 stop11h 35m

$1,654

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 12/20

7:15 am-5:20 pm

2 stops16h 05m

Chicago O'Hare Intl

Sun 12/28

6:30 pm-2:50 pm

2 stops14h 20m

$1,688

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 1/1

6:05 pm-2:20 pm

2 stops26h 15m

Chicago O'Hare Intl

Thu 1/8

5:20 pm-12:50 pm

1 stop13h 30m

$1,801

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 12/19

6:40 am-5:20 pm

2 stops16h 40m

Chicago O'Hare Intl

Fri 1/2

4:25 pm-10:00 am

1 stop11h 35m

$2,114

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 23 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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