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Cheap flights from London Southend Airport to Chicago from $506

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 10/1. 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
1 adult, Economy, 0 bags

Find the cheapest flights from London Southend Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:25 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
13h 45m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
5:10 pm - 10:30 amORD  Chicago O'Hare Intl-SEN London Southend
11h 20m1 stop Paris Charles de Gaulle
$827Multiple Airlines
Sun, Sep 6 - Sun, Sep 13
Multiple Airlines Logo
7:25 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
13h 45m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
5:10 pm - 10:30 amORD  Chicago O'Hare Intl-SEN London Southend
11h 20m1 stop Paris Charles de Gaulle
$828Multiple Airlines
Sun, Sep 6 - Sun, Sep 13
Multiple Airlines Logo
7:25 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
13h 45m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
5:10 pm - 10:25 amORD  Chicago O'Hare Intl-SEN London Southend
11h 15m1 stop Paris Charles de Gaulle
$906Multiple Airlines
Sun, Sep 6 - Sat, Sep 12
Multiple Airlines Logo
2:25 pm - 2:00 pmSEN  London Southend-ORD Chicago O'Hare Intl
29h 35m2 stops Paris Charles de Gaulle Dublin
Multiple Airlines Logo
6:30 pm - 6:45 pmORD  Chicago O'Hare Intl-SEN London Southend
18h 15m2 stops Reykjavik Keflavik Intl Paris Charles de Gaulle
$1,201Multiple Airlines
Fri, Nov 20 - Sat, Nov 21
Multiple Airlines Logo
11:10 am - 9:25 pmSEN  London Southend-ORD Chicago O'Hare Intl
16h 15m2 stops Paris Charles de Gaulle Reykjavik Keflavik Intl
Multiple Airlines Logo
10:25 pm - 7:20 pmORD  Chicago O'Hare Intl-SEN London Southend
14h 55m2 stops Reykjavik Keflavik Intl Paris Charles de Gaulle
$1,292Multiple Airlines
Mon, Aug 24 - Sat, Aug 29
Multiple Airlines Logo
7:15 am - 2:25 pmSEN  London Southend-ORD Chicago O'Hare Intl
13h 10m1 stop Amsterdam Schiphol
Multiple Airlines Logo
12:15 pm - 9:55 amORD  Chicago O'Hare Intl-SEN London Southend
15h 40m2 stops Minneapolis St Paul Amsterdam Schiphol
$1,475Multiple Airlines
Sat, Dec 19 - Fri, Jan 1
Multiple Airlines Logo
11:20 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
33h 50m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
10:25 pm - 10:25 amORD  Chicago O'Hare Intl-SEN London Southend
30h 00m2 stops Reykjavik Keflavik Intl Paris Charles de Gaulle
$1,717Multiple Airlines
Fri, Sep 4 - Fri, Sep 11
Multiple Airlines Logo
11:20 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
33h 50m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
10:25 pm - 10:25 amORD  Chicago O'Hare Intl-SEN London Southend
30h 00m2 stops Reykjavik Keflavik Intl Paris Charles de Gaulle
$2,077Multiple Airlines
Fri, Sep 4 - Fri, Sep 11
Multiple Airlines Logo
11:20 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
33h 50m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
6:00 pm - 9:45 pmORD  Chicago O'Hare Intl-SEN London Southend
21h 45m2 stops Lisbon Humberto Delgado Barcelona-El Prat
$2,199Multiple Airlines
Fri, Sep 4 - Fri, Sep 11
Multiple Airlines Logo
11:20 am - 3:10 pmSEN  London Southend-ORD Chicago O'Hare Intl
33h 50m1 stop Paris Charles de Gaulle
Multiple Airlines Logo
11:20 pm - 7:35 pmORD  Chicago O'Hare Intl-SEN London Southend
38h 15m3 stops Bogotá El Dorado Cartagena Rafael Nunez Amsterdam Schiphol
$3,072Multiple Airlines
Fri, Sep 4 - Fri, Sep 11

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Customize 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 832,500 searches. Data last updated August 8, 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

Cheapest round-trip

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 9/6

7:25 am-3:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Sun 9/13

5:10 pm-10:30 am

1 stop11h 20m

$827

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 9/6

7:25 am-3:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Sun 9/13

5:10 pm-10:30 am

1 stop11h 20m

$828
Quickest round-trip

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sun 9/6

7:25 am-3:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Sat 9/12

5:10 pm-10:25 am

1 stop11h 15m

$906

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Fri 11/20

2:25 pm-2:00 pm

2 stops29h 35m

Chicago O'Hare Intl

Sat 11/21

6:30 pm-6:45 pm

2 stops18h 15m

$1,201

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Mon 8/24

11:10 am-9:25 pm

2 stops16h 15m

Chicago O'Hare Intl

Sat 8/29

10:25 pm-7:20 pm

2 stops14h 55m

$1,292

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Sat 12/19

7:15 am-2:25 pm

1 stop13h 10m

Chicago O'Hare Intl

Fri 1/1

12:15 pm-9:55 am

2 stops15h 40m

$1,475

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Fri 9/4

11:20 am-3:10 pm

1 stop33h 50m

Chicago O'Hare Intl

Fri 9/11

10:25 pm-10:25 am

2 stops30h 00m

$1,717

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Fri 9/4

11:20 am-3:10 pm

1 stop33h 50m

Chicago O'Hare Intl

Fri 9/11

10:25 pm-10:25 am

2 stops30h 00m

$2,077

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Fri 9/4

11:20 am-3:10 pm

1 stop33h 50m

Chicago O'Hare Intl

Fri 9/11

6:00 pm-9:45 pm

2 stops21h 45m

$2,199

LondonChicago

SEN London Southend - ORD Chicago O'Hare Intl

SENORD

London Southend

Fri 9/4

11:20 am-3:10 pm

1 stop33h 50m

Chicago O'Hare Intl

Fri 9/11

11:20 pm-7:35 pm

3 stops38h 15m

$3,072

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 Thursday when prices can be found for as low as $894. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from London Southend Airport to Chicago for around $1,062.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from London Southend Airport to Chicago during this time can be as low as $900. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $960.

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 round-trip 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 45m

Direct flights

None
The fastest flight from London Southend Airport to Chicago takes 13h 45m
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

Frequently asked questions about flying from London Southend Airport to Chicago

  • How far is London Southend to Chicago by plane?

    The distance between London Southend and Chicago is about 3974.0 mi. Typically, this will take 13h 45m by plane in normal conditions.

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

    Prices for flights from London Southend Airport to Chicago were last updated today.

  • 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 that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from London.

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

Flights from London to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential London to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from London to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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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