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Cheap flights from London Southend Airport to Chicago from $457

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 3/5. 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 round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:10 am - 9:05 pm
SEN
-
ORD
18h 55m
2 stops
Multiple Airlines Logo
2:20 pm - 10:30 am
ORD
-
SEN
14h 10m
2 stops
$795Multiple Airlines
Wed, Mar 25 - Sun, Mar 29
Multiple Airlines Logo
2:10 pm - 3:10 pm
SEN
-
ORD
31h 00m
2 stops
Multiple Airlines Logo
7:25 pm - 9:45 pm
ORD
-
SEN
20h 20m
3 stops
$887Multiple Airlines
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
8:05 pm - 4:59 pm
SEN
-
ORD
26h 54m
3 stops
Multiple Airlines Logo
9:00 pm - 7:35 pm
ORD
-
SEN
16h 35m
3 stops
$1,067Multiple Airlines
Mon, Jun 1 - Sun, Jun 7
Multiple Airlines Logo
7:10 am - 4:10 pm
SEN
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
5:10 pm - 1:00 pm
ORD
-
SEN
13h 50m
1 stop
$1,084Multiple Airlines
Wed, Mar 25 - Wed, Apr 1
Multiple Airlines Logo
2:20 pm - 3:00 pm
SEN
-
ORD
29h 40m
2 stops
Multiple Airlines Logo
2:20 pm - 10:30 am
ORD
-
SEN
14h 10m
2 stops
$1,149Multiple Airlines
Sun, Mar 22 - Sun, Mar 29
Multiple Airlines Logo
7:15 am - 5:36 am
SEN
-
ORD
27h 21m
3 stops
Multiple Airlines Logo
12:50 pm - 10:30 am
ORD
-
SEN
16h 40m
2 stops
$1,420Multiple Airlines
Sat, Mar 21 - Sun, Mar 22
Multiple Airlines Logo
6:40 am - 3:20 pm
SEN
-
ORD
13h 40m
1 stop
Multiple Airlines Logo
5:25 pm - 10:20 am
ORD
-
SEN
11h 55m
1 stop
$1,455Multiple Airlines
Fri, Mar 13 - Mon, Mar 16
Multiple Airlines Logo
6:40 am - 3:20 pm
SEN
-
ORD
13h 40m
1 stop
Multiple Airlines Logo
5:25 pm - 10:20 am
ORD
-
SEN
11h 55m
1 stop
$1,755Multiple Airlines
Fri, Mar 20 - Mon, Mar 23
Multiple Airlines Logo
4:55 pm - 2:15 pm
SEN
-
ORD
27h 20m
1 stop
Multiple Airlines Logo
7:30 am - 9:45 pm
ORD
-
SEN
32h 15m
2 stops
$2,325Multiple Airlines
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
11:10 am - 3:10 pm
SEN
-
ORD
34h 00m
1 stop
Multiple Airlines Logo
9:40 pm - 7:55 am
ORD
-
SEN
28h 15m
2 stops
$2,363Multiple Airlines
Mon, Apr 13 - Mon, Apr 20

momondo Fare Finder

 
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 March 1, 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 3/25

7:10 am-9:05 pm

2 stops18h 55m

Chicago O'Hare Intl

Sun 3/29

2:20 pm-10:30 am

2 stops14h 10m

$795

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 4/10

2:10 pm-3:10 pm

2 stops31h 00m

Chicago O'Hare Intl

Fri 4/17

7:25 pm-9:45 pm

3 stops20h 20m

$887

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 6/1

8:05 pm-4:59 pm

3 stops26h 54m

Chicago O'Hare Intl

Sun 6/7

9:00 pm-7:35 pm

3 stops16h 35m

$1,067

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 3/25

7:10 am-4:10 pm

1 stop14h 00m

Chicago O'Hare Intl

Wed 4/1

5:10 pm-1:00 pm

1 stop13h 50m

$1,084

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 3/22

2:20 pm-3:00 pm

2 stops29h 40m

Chicago O'Hare Intl

Sun 3/29

2:20 pm-10:30 am

2 stops14h 10m

$1,149

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 3/21

7:15 am-5:36 am

3 stops27h 21m

Chicago O'Hare Intl

Sun 3/22

12:50 pm-10:30 am

2 stops16h 40m

$1,420

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 3/13

6:40 am-3:20 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 3/16

5:25 pm-10:20 am

1 stop11h 55m

$1,455

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 3/20

6:40 am-3:20 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 3/23

5:25 pm-10:20 am

1 stop11h 55m

$1,755

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 4/10

4:55 pm-2:15 pm

1 stop27h 20m

Chicago O'Hare Intl

Fri 4/17

7:30 am-9:45 pm

2 stops32h 15m

$2,325

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 4/13

11:10 am-3:10 pm

1 stop34h 00m

Chicago O'Hare Intl

Mon 4/20

9:40 pm-7:55 am

2 stops28h 15m

$2,363

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 $783. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from London Southend Airport to Chicago for around $891.

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 in the morning. Flights from London Southend Airport to Chicago during this time can be as low as $828. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $959.

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 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?

    The distance between London Southend and Chicago is about 3974.0 mi. Typically, this will take 13h 40m 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
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