HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$480+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Southend to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 12, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$754
(Booking.com)

One-way from

$480
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$624
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. 14% potential increase in price ($119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 12, 2026.

This Booking.com deal was found by Cheapflights users on 1/11. 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 1/226:50 am
SEN
-
ORD
3 stops45h 52m
Multiple Airlines
Sun 1/256:30 pm
ORD
-
SEN
3 stops22h 30m
Multiple Airlines
Deal found 1/11$754
This Booking.com deal was found by Cheapflights users on 1/11. 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 1/267:15 am
SEN
-
ORD
3 stops40h 33m
Multiple Airlines
Sun 2/85:20 pm
ORD
-
SEN
1 stop11h 10m
Multiple Airlines
Deal found 1/11$943
This Kiwi.com deal was found by Cheapflights users on 1/11. 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.
Wed 2/2510:35 am
SEN
-
ORD
2 stops39h 25m
Multiple Airlines
Wed 3/44:25 pm
ORD
-
SEN
1 stop18h 50m
Multiple Airlines
Deal found 1/11$1,279
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Mon 1/197:15 am
SEN
-
ORD
1 stop13h 55m
Multiple Airlines
Sun 2/15:20 pm
ORD
-
SEN
1 stop11h 10m
Multiple Airlines
Deal found 1/12$1,365
This Kiwi.com deal was found by Cheapflights users on 1/11. 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.
Sat 2/287:15 am
SEN
-
ORD
2 stops16h 46m
Multiple Airlines
Sat 3/74:25 pm
ORD
-
SEN
1 stop21h 45m
Multiple Airlines
Deal found 1/11$1,481
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Mon 2/27:15 am
SEN
-
ORD
1 stop13h 55m
Multiple Airlines
Sun 2/85:40 pm
ORD
-
SEN
2 stops39h 15m
Multiple Airlines
Deal found 1/12$2,148

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 January 12, 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

Thu 1/22

6:50 am-10:42 pm

3 stops45h 52m

Chicago O'Hare Intl

Sun 1/25

6:30 pm-11:00 pm

3 stops22h 30m

$754

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 2/25

10:35 am-8:00 pm

2 stops39h 25m

Chicago O'Hare Intl

Wed 3/4

4:25 pm-5:15 pm

1 stop18h 50m

$1,279

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 2/28

7:15 am-6:01 pm

2 stops16h 46m

Chicago O'Hare Intl

Sat 3/7

4:25 pm-8:10 pm

1 stop21h 45m

$1,481

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 2/2

7:15 am-3:10 pm

1 stop13h 55m

Chicago O'Hare Intl

Sun 2/8

5:40 pm-2:55 pm

2 stops39h 15m

$2,148

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 5/12

8:25 pm-2:15 pm

2 stops23h 50m

$480

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 2/4

7:10 am-8:10 pm

2 stops19h 00m

$535

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 3/22

7:10 am-8:55 pm

3 stops42h 45m

$537

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 5/22

7:30 am-3:10 pm

2 stops37h 40m

$539

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 3/21

8:00 pm-9:00 pm

2 stops30h 00m

$546

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 6/19

10:00 pm-9:15 pm

3 stops29h 15m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 14 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 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.