Find flights
When to book

Cheap flights from London Southend Airport to Chicago from £340

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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — CHI
1 Apr — 8 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 2 March 2026.

Wed 15/415:40
SEN
-
ORD
2 stops28h 45m
Multiple Airlines
Wed 22/417:10
ORD
-
SEN
1 stop13h 50m
Multiple Airlines
Deal found 1/3£767
Mon 1/620:05
SEN
-
ORD
3 stops26h 54m
Multiple Airlines
Sun 7/621:00
ORD
-
SEN
3 stops16h 35m
Multiple Airlines
Deal found 28/2£791
Mon 30/307:50
SEN
-
ORD
2 stops33h 03m
Multiple Airlines
Thu 9/415:45
ORD
-
SEN
2 stops15h 55m
Multiple Airlines
Deal found 1/3£948
Tue 10/307:35
SEN
-
ORD
2 stops16h 20m
Multiple Airlines
Sun 15/320:40
ORD
-
SEN
2 stops13h 10m
Multiple Airlines
Deal found 27/2£1,021
Fri 13/306:40
SEN
-
ORD
1 stop13h 40m
Multiple Airlines
Mon 16/317:25
ORD
-
SEN
1 stop11h 55m
Multiple Airlines
Deal found 27/2£1,079
Fri 20/306:40
SEN
-
ORD
1 stop13h 40m
Multiple Airlines
Mon 23/317:25
ORD
-
SEN
1 stop11h 55m
Multiple Airlines
Deal found 26/2£1,301
Mon 13/411:10
SEN
-
ORD
1 stop34h 00m
Multiple Airlines
Mon 20/421:40
ORD
-
SEN
2 stops28h 15m
Multiple Airlines
Deal found 26/2£1,752
Sat 28/220:00
SEN
-
ORD
2 stops24h 45m
Multiple Airlines
Sat 7/316:25
ORD
-
SEN
1 stop21h 45m
Multiple Airlines
Deal found 28/2£1,956

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 2 March 2026.

Round-trip from

£767

One-way from

£340

Popular in

July

Cheapest in

September

Average price

£519
15/4-22/4
  • 15/4-22/4
  • 3 total stops
  • 42h 35m total
  • London to Chicago
Search Deals
18/3
  • 18/3
  • 2 total stops
  • 32h 10m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£57 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 2026
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 2 March 2026.
Use the filters below to find and compare flights from London Southend Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 15/4

15:40-14:25

2 stops28h 45m

Chicago O'Hare Intl

Wed 22/4

17:10-13:00

1 stop13h 50m

£767

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 1/6

20:05-16:59

3 stops26h 54m

Chicago O'Hare Intl

Sun 7/6

21:00-19:35

3 stops16h 35m

£791

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 30/3

07:50-10:53

2 stops33h 03m

Chicago O'Hare Intl

Thu 9/4

15:45-13:40

2 stops15h 55m

£948

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 20/3

06:40-15:20

1 stop13h 40m

Chicago O'Hare Intl

Mon 23/3

17:25-10:20

1 stop11h 55m

£1,301

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 13/4

11:10-15:10

1 stop34h 00m

Chicago O'Hare Intl

Mon 20/4

21:40-07:55

2 stops28h 15m

£1,752

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 18/3

07:10-10:20

2 stops32h 10m

£340

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 10/3

20:20-00:40

3 stops33h 20m

£346

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 7/3

15:00-14:45

3 stops29h 45m

£347

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 12/3

06:30-16:25

3 stops38h 55m

£366

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 8/3

07:10-23:40

3 stops46h 30m

£372

Flights are sorted by cheapest return flights first.

Deals found on 26/2

Showing 1-10 of 12 resultsSorted by cheapest first
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

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

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Southend today with Cheapflights!

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.

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.