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Cheap flights from London Southend Airport to Chicago from £346

SEN — CHI
28 Sep — 5 Oct1
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

Wed 21/1015:40 -
2 stops30h 30m
Mon 26/1020:15 -
2 stops21h 10m
Deal found 27/8£548
Sun 25/1015:55 -
3 stops30h 50m
Sat 31/1020:15 -
2 stops17h 30m
Deal found 25/8£556
Fri 23/1016:55 -
2 stops29h 15m
Tue 27/1020:15 -
2 stops18h 25m
Deal found 29/8£607
Thu 8/1013:55 -
2 stops32h 15m
Thu 15/1019:15 -
2 stops18h 20m
Deal found 24/8£631
Sun 4/1016:55 -
2 stops29h 15m
Sat 10/1019:15 -
2 stops18h 20m
Deal found 28/8£646
Tue 20/1007:00 -
2 stops18h 15m
Tue 27/1019:30 -
2 stops16h 10m
Deal found 28/8£660
Thu 22/1006:30 -
2 stops18h 45m
Sat 31/1019:30 -
2 stops18h 15m
Deal found 25/8£678
Sun 30/807:35 -
2 stops19h 50m
Sun 6/922:25 -
2 stops15h 10m
Deal found 25/8£822
Sun 30/807:35 -
2 stops19h 50m
Wed 2/919:25 -
2 stops15h 15m
Deal found 28/8£990
Sun 13/907:25 -
1 stop13h 50m
Thu 17/917:10 -
1 stop11h 35m
Deal found 27/8£1,551

Find flight deals from Southend to Chicago

Round-trip from

£548

One-way from

£346

Popular in

August

Cheapest in

February

Average price

£722
21/10-26/10
  • 21/10-26/10
  • 4 total stops
  • 51h 40m total
  • London to Chicago
Search Deals
22/10
  • 22/10
  • 3 total stops
  • 30h 35m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (£46 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 August 2026
Search Deals

Cheapflights Fare Finder

 
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

Cheapest return flight

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Wed 21/10

15:40-16:10

2 stops30h 30m

Chicago O'Hare Intl

Mon 26/10

20:15-22:25

2 stops21h 10m

£548

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Fri 23/10

16:55-16:10

2 stops29h 15m

Chicago O'Hare Intl

Tue 27/10

20:15-19:40

2 stops18h 25m

£607

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Thu 8/10

13:55-16:10

2 stops32h 15m

Chicago O'Hare Intl

Thu 15/10

19:15-19:35

2 stops18h 20m

£631

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 4/10

16:55-16:10

2 stops29h 15m

Chicago O'Hare Intl

Sat 10/10

19:15-19:35

2 stops18h 20m

£646

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Tue 20/10

07:00-19:15

2 stops18h 15m

Chicago O'Hare Intl

Tue 27/10

19:30-16:40

2 stops16h 10m

£660

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Thu 22/10

06:30-19:15

2 stops18h 45m

Chicago O'Hare Intl

Sat 31/10

19:30-18:45

2 stops18h 15m

£678

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 25/10

08:10-15:10

2 stops36h 00m

Chicago O'Hare Intl

Sat 31/10

19:25-18:45

1 stop18h 20m

£914
Fastest return journey

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 13/9

07:25-15:15

1 stop13h 50m

Chicago O'Hare Intl

Thu 17/9

17:10-10:45

1 stop11h 35m

£1,551
Cheapest one-way
Fastest single journey

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 25/10

19:15-18:50

3 stops28h 35m

£359

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Wed 9/9

08:25-12:40

2 stops34h 15m

£368

Flights are sorted by cheapest return flights first.

Deals found on 27/8

Showing 1-10 of 17 resultsSorted by cheapest first
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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

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

  • 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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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.

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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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