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Cheap flights from London Southend Airport to Chicago from £428

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 2/2. 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
18:05 - 15:10
SEN
-
ORD
27h 05m1 stop
Multiple Airlines Logo
18:30 - 11:25
ORD
-
SEN
34h 55m2 stops
£1,650Multiple Airlines
Sun, 15 Feb - Sat, 21 Feb

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 21 December 2025.
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

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 15/2

18:05-15:10

1 stop27h 05m

Chicago O'Hare Intl

Sat 21/2

18:30-11:25

2 stops34h 55m

£1,650

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 2/2

07:15-17:20

2 stops16h 05m

£428

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 11/2

07:10-17:20

2 stops16h 10m

£429

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 12/6

07:30-15:10

3 stops37h 40m

£431

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 29/5

11:20-21:40

2 stops16h 20m

£457

LondonChicago

SEN - ORD

SENORD

London Southend

Wed 31/12

07:10-08:31

3 stops31h 21m

£522

LondonChicago

SEN - ORD

SENORD

London Southend

Sun 22/3

11:55-11:05

2 stops28h 10m

£525

LondonChicago

SEN - ORD

SENORD

London Southend

Sat 28/3

20:00-19:50

2 stops28h 50m

£528

LondonChicago

SEN - ORD

SENORD

London Southend

Mon 29/12

11:15-18:25

2 stops37h 10m

£573

LondonChicago

SEN - ORD

SENORD

London Southend

Fri 26/12

12:35-10:05

2 stops27h 30m

£686

Flights are sorted by cheapest return flights first.

Showing 1-10 of 11 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 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 £614. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Chicago O'Hare Intl Airport on Saturday is £669.

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 in the evening when flights can be purchased for as low as £568. In contrast, the most expensive time of day to depart to Chicago O'Hare Intl Airport is in the afternoon when prices are around £661.

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

16h 40m

Direct flights

None
The fastest flight from London Southend Airport to Chicago O'Hare Intl Airport takes 16h 40m
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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  • 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 16h 40m, 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
Racine
Evanston
Schaumburg
Northbrook
Lincolnshire
Lake Geneva
Joliet
Oak Park
Oak Brook
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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