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Cheap flights from London Southend Airport to Chicago from $575

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 8/22. 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
7:45 am - 9:25 pm
SEN
-
ORD
19h 40m
2 stops
Multiple Airlines Logo
7:25 pm - 4:40 pm
ORD
-
SEN
15h 15m
2 stops
$817Multiple Airlines
Mon, Jul 13 - Wed, Jul 22
Multiple Airlines Logo
11:10 am - 9:25 pm
SEN
-
ORD
16h 15m
2 stops
Multiple Airlines Logo
10:25 pm - 7:20 pm
ORD
-
SEN
14h 55m
2 stops
$840Multiple Airlines
Mon, Aug 24 - Sat, Aug 29
Multiple Airlines Logo
7:20 pm - 4:57 pm
SEN
-
ORD
27h 37m
3 stops
Multiple Airlines Logo
7:25 pm - 4:40 pm
ORD
-
SEN
15h 15m
2 stops
$1,081Multiple Airlines
Mon, Jul 20 - Wed, Jul 29
Multiple Airlines Logo
7:50 pm - 2:25 pm
SEN
-
ORD
24h 35m
2 stops
Multiple Airlines Logo
5:10 pm - 7:20 pm
ORD
-
SEN
20h 10m
1 stop
$1,090Multiple Airlines
Sun, Aug 23 - Sat, Aug 29
Multiple Airlines Logo
6:30 am - 3:10 pm
SEN
-
ORD
38h 40m
3 stops
Multiple Airlines Logo
7:25 pm - 4:40 pm
ORD
-
SEN
15h 15m
2 stops
$1,231Multiple Airlines
Mon, Jul 20 - Wed, Jul 29
Multiple Airlines Logo
4:35 pm - 4:00 pm
SEN
-
ORD
29h 25m
2 stops
Multiple Airlines Logo
5:10 pm - 10:45 am
ORD
-
SEN
11h 35m
1 stop
$1,397Multiple Airlines
Thu, Aug 6 - Thu, Aug 13
Multiple Airlines Logo
7:35 am - 2:15 pm
SEN
-
ORD
12h 40m
1 stop
Multiple Airlines Logo
4:20 pm - 10:15 am
ORD
-
SEN
11h 55m
1 stop
$1,720Multiple Airlines
Sun, Jul 12 - Sat, Jul 18
Multiple Airlines Logo
7:35 am - 2:15 pm
SEN
-
ORD
12h 40m
1 stop
Multiple Airlines Logo
4:20 pm - 10:15 am
ORD
-
SEN
11h 55m
1 stop
$1,722Multiple Airlines
Sun, Jul 12 - Sat, Jul 18
Multiple Airlines Logo
7:50 pm - 3:10 pm
SEN
-
ORD
25h 20m
1 stop
Multiple Airlines Logo
5:10 pm - 7:20 pm
ORD
-
SEN
20h 10m
1 stop
$2,450Multiple Airlines
Sun, Aug 23 - Sat, Aug 29
Multiple Airlines Logo
1:45 pm - 3:10 pm
SEN
-
ORD
31h 25m
1 stop
Multiple Airlines Logo
5:10 pm - 10:45 am
ORD
-
SEN
11h 35m
1 stop
$2,585Multiple Airlines
Thu, Aug 6 - Thu, Aug 13

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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 June 27, 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 - ORD

SENORD

London Southend

Mon 7/13

7:45 am-9:25 pm

2 stops19h 40m

Chicago O'Hare Intl

Wed 7/22

7:25 pm-4:40 pm

2 stops15h 15m

$817

LondonChicago

SEN - ORD

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

$840

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 7/20

7:20 pm-4:57 pm

3 stops27h 37m

Chicago O'Hare Intl

Wed 7/29

7:25 pm-4:40 pm

2 stops15h 15m

$1,081

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 8/23

7:50 pm-2:25 pm

2 stops24h 35m

Chicago O'Hare Intl

Sat 8/29

5:10 pm-7:20 pm

1 stop20h 10m

$1,090

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 7/20

6:30 am-3:10 pm

3 stops38h 40m

Chicago O'Hare Intl

Wed 7/29

7:25 pm-4:40 pm

2 stops15h 15m

$1,231

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 8/6

4:35 pm-4:00 pm

2 stops29h 25m

Chicago O'Hare Intl

Thu 8/13

5:10 pm-10:45 am

1 stop11h 35m

$1,397
Quickest round-trip

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 7/12

7:35 am-2:15 pm

1 stop12h 40m

Chicago O'Hare Intl

Sat 7/18

4:20 pm-10:15 am

1 stop11h 55m

$1,720

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 7/12

7:35 am-2:15 pm

1 stop12h 40m

Chicago O'Hare Intl

Sat 7/18

4:20 pm-10:15 am

1 stop11h 55m

$1,722

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 8/23

7:50 pm-3:10 pm

1 stop25h 20m

Chicago O'Hare Intl

Sat 8/29

5:10 pm-7:20 pm

1 stop20h 10m

$2,450

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 8/6

1:45 pm-3:10 pm

1 stop31h 25m

Chicago O'Hare Intl

Thu 8/13

5:10 pm-10:45 am

1 stop11h 35m

$2,585

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 Wednesday when prices can be found for as low as $879. 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 $1,000.

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 $899. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $992.

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

16h 15m

Direct flights

None
The fastest flight from London Southend Airport to Chicago takes 16h 15m
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 16h 15m 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
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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