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Cheap flights from London Southend Airport to Chicago from £370

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 10/4. 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
14:30 - 15:10
SEN
-
ORD
30h 40m
2 stops
Multiple Airlines Logo
17:10 - 13:00
ORD
-
SEN
13h 50m
1 stop
£1,117Multiple Airlines
Fri, 15 May - Wed, 27 May
Multiple Airlines Logo
17:15 - 19:15
SEN
-
ORD
32h 00m
2 stops
Multiple Airlines Logo
17:10 - 10:45
ORD
-
SEN
11h 35m
1 stop
£1,120Multiple Airlines
Thu, 14 May - Thu, 21 May
Multiple Airlines Logo
06:30 - 09:40
SEN
-
ORD
33h 10m
2 stops
Multiple Airlines Logo
16:20 - 19:35
ORD
-
SEN
21h 15m
1 stop
£1,200Multiple Airlines
Tue, 5 May - Sun, 10 May
Multiple Airlines Logo
16:50 - 16:00
SEN
-
ORD
29h 10m
2 stops
Multiple Airlines Logo
17:10 - 10:25
ORD
-
SEN
11h 15m
1 stop
£1,257Multiple Airlines
Sat, 16 May - Sat, 23 May
Multiple Airlines Logo
11:20 - 15:10
SEN
-
ORD
33h 50m
1 stop
Multiple Airlines Logo
17:10 - 13:00
ORD
-
SEN
13h 50m
1 stop
£2,070Multiple Airlines
Fri, 15 May - Wed, 27 May
Multiple Airlines Logo
10:10 - 15:10
SEN
-
ORD
35h 00m
1 stop
Multiple Airlines Logo
17:10 - 10:45
ORD
-
SEN
11h 35m
1 stop
£2,082Multiple Airlines
Thu, 14 May - Thu, 21 May

momondo Fare Finder

 
Customise your flight search to find flights from London Southend Airport to Chicago O'Hare Intl Airport 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 3 April 2026.
Use the filters below to find and compare flights from London Southend Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 15/5

14:30-15:10

2 stops30h 40m

Chicago O'Hare Intl

Wed 27/5

17:10-13:00

1 stop13h 50m

£1,117

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 14/5

17:15-19:15

2 stops32h 00m

Chicago O'Hare Intl

Thu 21/5

17:10-10:45

1 stop11h 35m

£1,120

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 5/5

06:30-09:40

2 stops33h 10m

Chicago O'Hare Intl

Sun 10/5

16:20-19:35

1 stop21h 15m

£1,200
Fastest return journey

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 16/5

16:50-16:00

2 stops29h 10m

Chicago O'Hare Intl

Sat 23/5

17:10-10:25

1 stop11h 15m

£1,257

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 15/5

11:20-15:10

1 stop33h 50m

Chicago O'Hare Intl

Wed 27/5

17:10-13:00

1 stop13h 50m

£2,070

LondonChicago

SEN - ORD

SENORD

London Southend

Thu 14/5

10:10-15:10

1 stop35h 00m

Chicago O'Hare Intl

Thu 21/5

17:10-10:45

1 stop11h 35m

£2,082
Cheapest one-way

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 10/4

22:00-16:00

3 stops48h 00m

£370

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 15/9

20:25-12:40

3 stops46h 15m

£371

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 1/5

22:00-16:00

3 stops48h 00m

£372

LondonChicago

SEN - ORD

SENORD

London Southend

Tue 15/9

20:25-12:40

3 stops46h 15m

£373

Flights are sorted by cheapest return flights first.

Showing 1-10 of 16 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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart from London Southend Airport to Chicago O'Hare Intl Airport is on a Wednesday. Travellers who choose to depart for Chicago O'Hare Intl Airport on a Wednesday will often find tickets for as low as £648. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Chicago O'Hare Intl Airport on Sunday is £676.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest time of day to fly to Chicago O'Hare Intl Airport is at midday when flights can be purchased for as low as £651. In contrast, the most expensive time of day to depart to Chicago O'Hare Intl Airport is in the afternoon when prices are around £668.

When to book flights from London Southend Airport to Chicago O'Hare Intl Airport

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

Cheap London Southend Airport to Chicago O'Hare Intl Airport (SEN to ORD) flight deals and tips

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

Fastest flight time

13h 45m

Direct flights

None
The fastest flight from London Southend Airport to Chicago O'Hare Intl Airport takes 13h 45m
There are no direct flights from London Southend Airport to Chicago O'Hare Intl Airport. There are no popular flight routes from London Southend Airport to Chicago O'Hare Intl Airport.
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Frequently asked questions about flying from London Southend Airport to Chicago O'Hare Intl Airport

  • How far is London Southend to Chicago O'Hare Intl by plane?

    London Southend and Chicago O'Hare Intl are 3979.6 mi apart from one another. Flights usually cover this in 13h 45m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from London Southend Airport to Chicago O'Hare Intl Airport are updated daily.

  • How old do you have to be to fly from London Southend Airport to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lincolnshire
Racine
Evanston
Lake Geneva
Joliet
Oak Park
Schaumburg
Northbrook
Elgin
Rosemont

Why use momondo?

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

Finding the right flight to Chicago from London is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Chicago from London which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from London.

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

Yes momondo offers price alerts on flights to Chicago from London. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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