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Cheap flights from London Southend Airport to Chicago from £347

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from London Southend Airport to Chicago departing on 18/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Find the cheapest flights from London Southend Airport to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
07:10 - 16:45
SEN
-
ORD
15h 35m
2 stops
Multiple Airlines Logo
19:20 - 20:50
ORD
-
SEN
19h 30m
2 stops
£718Multiple Airlines
Wed, 25 Feb - Sat, 28 Feb
Multiple Airlines Logo
07:20 - 20:55
SEN
-
ORD
18h 35m
3 stops
Multiple Airlines Logo
12:50 - 11:40
ORD
-
SEN
17h 50m
2 stops
£868Multiple Airlines
Mon, 9 Mar - Thu, 12 Mar
Multiple Airlines Logo
06:40 - 15:20
SEN
-
ORD
13h 40m
1 stop
Multiple Airlines Logo
17:25 - 10:00
ORD
-
SEN
11h 35m
1 stop
£913Multiple Airlines
Fri, 13 Mar - Fri, 20 Mar
Multiple Airlines Logo
07:15 - 15:20
SEN
-
ORD
13h 05m
1 stop
Multiple Airlines Logo
17:10 - 19:35
ORD
-
SEN
20h 25m
2 stops
£941Multiple Airlines
Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
07:15 - 15:20
SEN
-
ORD
13h 05m
1 stop
Multiple Airlines Logo
17:10 - 19:35
ORD
-
SEN
20h 25m
2 stops
£992Multiple Airlines
Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
06:40 - 15:20
SEN
-
ORD
13h 40m
1 stop
Multiple Airlines Logo
17:25 - 10:00
ORD
-
SEN
11h 35m
1 stop
£1,114Multiple Airlines
Fri, 13 Mar - Fri, 20 Mar
Multiple Airlines Logo
07:25 - 13:35
SEN
-
ORD
36h 10m
2 stops
Multiple Airlines Logo
17:10 - 10:30
ORD
-
SEN
11h 20m
1 stop
£1,152Multiple Airlines
Sun, 29 Mar - Sun, 5 Apr
Multiple Airlines Logo
07:25 - 15:10
SEN
-
ORD
13h 45m
1 stop
Multiple Airlines Logo
17:10 - 10:30
ORD
-
SEN
11h 20m
1 stop
£1,199Multiple Airlines
Sun, 29 Mar - Sun, 5 Apr
Multiple Airlines Logo
07:15 - 15:20
SEN
-
ORD
13h 05m
1 stop
Multiple Airlines Logo
17:10 - 10:25
ORD
-
SEN
11h 15m
1 stop
£2,073Multiple Airlines
Sat, 28 Mar - Sat, 4 Apr

momondo Fare Finder

 
Customise your flight search to find flights from London Southend Airport 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, momondo users made 279,928 searches. Data last updated 13 February 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 25/2

07:10-16:45

2 stops15h 35m

Chicago O'Hare Intl

Sat 28/2

19:20-20:50

2 stops19h 30m

£718

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 9/3

07:20-20:55

3 stops18h 35m

Chicago O'Hare Intl

Thu 12/3

12:50-11:40

2 stops17h 50m

£868

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 13/3

06:40-15:20

1 stop13h 40m

Chicago O'Hare Intl

Fri 20/3

17:25-10:00

1 stop11h 35m

£913

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 28/3

07:15-15:20

1 stop13h 05m

Chicago O'Hare Intl

Sat 4/4

17:10-19:35

2 stops20h 25m

£941

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 28/3

07:15-15:20

1 stop13h 05m

Chicago O'Hare Intl

Sat 4/4

17:10-19:35

2 stops20h 25m

£992

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 13/3

06:40-15:20

1 stop13h 40m

Chicago O'Hare Intl

Fri 20/3

17:25-10:00

1 stop11h 35m

£1,114

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 29/3

07:25-13:35

2 stops36h 10m

Chicago O'Hare Intl

Sun 5/4

17:10-10:30

1 stop11h 20m

£1,152

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 29/3

07:25-15:10

1 stop13h 45m

Chicago O'Hare Intl

Sun 5/4

17:10-10:30

1 stop11h 20m

£1,199

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 28/3

07:15-15:20

1 stop13h 05m

Chicago O'Hare Intl

Sat 4/4

17:10-10:25

1 stop11h 15m

£2,073

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 18/3

07:10-06:08

3 stops27h 58m

£347

Flights are sorted by cheapest return flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
1
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See travel insights to Chicago from

How to get the cheapest flight ticket from London Southend Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as £612. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Saturday, with ticket prices averaging around £649.

What is the cheapest time of day to depart on your flight to Chicago?

Flying to Chicago from London Southend Airport at midday is the least expensive time of day to depart. momondo users have found prices as low as £626 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £659.

When to book flights from London Southend Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from London Southend Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap London Southend Airport to Chicago (SEN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from London Southend Airport to Chicago

Fastest flight time

13h 40m

Direct flights

None
The fastest flight from London Southend Airport to Chicago takes 13h 40m
There are no direct flights from London Southend Airport to Chicago. There are no popular flight routes from London Southend Airport to Chicago.
Search flight deals

  • How far is London Southend to Chicago by plane?

    London Southend and Chicago are 3974.0 mi apart from one another. 13h 40m is a normal flight duration for this route.

  • When did momondo last update prices for flights from London Southend Airport to Chicago?

    Prices for flights from London Southend Airport to Chicago are updated daily.

  • How old do you have to be to fly from London Southend Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from London Southend Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from London to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from London to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from London to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from London with this policy.

How can momondo help me find flights from London to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from London. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from London to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of London to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport