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Cheap Flights from London Southend (SEN) to Chicago (CHIA)

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      Travellers and cabin class, 1 Adult, Economy

      Compare London Southend to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

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      Flight deals from London Southend to Chicago

      Looking for a cheap last-minute deal or the best return flight from London Southend Airport to Chicago? If you want to travel next month, return fares start from £578. Find the lowest prices on one-way and return tickets right here.
      Chicago.£288 per passenger.Departing Tue, 19 Jan.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Tue, 19 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From £288, select.
      Chicago.£306 per passenger.Departing Tue, 23 Feb.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Tue, 23 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From £306, select.
      Chicago.£307 per passenger.Departing Tue, 2 Mar.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Tue, 2 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From £307, select.
      Chicago.£320 per passenger.Departing Thu, 5 Nov.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From £320, select.
      Chicago.£320 per passenger.Departing Mon, 12 Apr.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Mon, 12 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From £320, select.
      Chicago.£321 per passenger.Departing Thu, 10 Dec.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Thu, 10 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From £321, select.
      Chicago.£330 per passenger.Departing Thu, 6 May.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Thu, 6 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From £330, select.
      Chicago.£338 per passenger.Departing Mon, 7 Jun.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Mon, 7 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From £338, select.
      Chicago.£346 per passenger.Departing Wed, 25 Aug.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Wed, 25 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From £346, select.
      Chicago.£371 per passenger.Departing Mon, 6 Sep.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Mon, 6 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From £371, select.
      Chicago.£400 per passenger.Departing Wed, 14 Oct.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Wed, 14 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From £400, select.
      Chicago.£458 per passenger.Departing Wed, 14 Jul.One-way flight with easyJet.Outbound indirect flight with easyJet, departs from London Southend on Wed, 14 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From £458, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from London Southend to Chicago found in the last 4 days, and are subject to change and availability.

      What’s the cheapest month to fly from London Southend Airport to Chicago?

      Right now, flights from London Southend Airport to Chicago are cheapest in January, with prices from £288. That's £170 less than you’d pay in July.
      Oct
      from £400
      Nov
      from £320
      Dec
      from £321
      Jan
      from £288
      Feb
      from £306
      Mar
      from £307
      Apr
      from £320
      May
      from £330
      Jun
      from £338
      Jul
      from £458
      Aug
      from £346
      Sep
      from £371
      Cheapest month:January
      Most expensive month:July

      When’s the best time to visit Chicago?

      We analysed thousands of flight and hotel prices, plus a whole heap of weather data, to show you what Chicago is typically like each month. If you're after a great deal, November currently has the lowest return flights from £578. But if you're searching for sunshine, July is the warmest month, with average temperatures of 20°C - 27°C.

      October

      Temperature10°C - 18°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£682
      Cheapest 3-star hotel£46
      Find a flight

      November

      Temperature3°C - 10°C
      RainfallDry
      (21–60mm)
      Cheapest return flight£578
      Cheapest 3-star hotel£83
      Find a flight

      December

      Temperature-2°C - 4°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£596
      Cheapest 3-star hotel£60
      Find a flight

      January

      Temperature-5°C - 0°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£673
      Cheapest 3-star hotel£15
      Find a flight

      February

      Temperature-5°C - 3°C
      RainfallDry
      (21–60mm)
      Cheapest return flight£696
      Cheapest 3-star hotel£70
      Find a flight

      March

      Temperature1°C - 10°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£657
      Cheapest 3-star hotel£39
      Find a flight

      April

      Temperature6°C - 15°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£695
      Cheapest 3-star hotel£49
      Find a flight

      May

      Temperature11°C - 20°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£907
      Cheapest 3-star hotel£122
      Find a flight

      June

      Temperature17°C - 27°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£1,001
      Cheapest 3-star hotel£128
      Find a flight

      July

      Temperature20°C - 27°C
      RainfallModerate
      (61–120mm)
      Cheapest return flight£1,073
      Cheapest 3-star hotel£130
      Find a flight

      Alternative London Southend to Chicago routes

      Looking for the cheapest, fastest or easiest route from London Southend to Chicago? You could fly into the following airports instead.

      Chicago Midway

      9 miles from central Chicago
      Closest
      from £361
      Search flights

      Chicago O'Hare International

      16 miles from central Chicago
      Cheapest
      from £288
      Search flights

      Chicago Rockford

      79 miles from central Chicago
      from £454
      Search flights

      London to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found£288
      Cheapest month to flyJanuary

      Finding cheap flights from London Southend to Chicago: Frequently asked questions

      There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
      The best price we found for a return flight from London Southend to Chicago is £574. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      Currently, there are no airlines that fly direct from London Southend to Chicago. But we found flights with one or more stops from £574.
      As of October 2026, there are no flights flying from London Southend to Chicago.
      The cheapest month to fly from London Southend to Chicago is usually October.
      If you're flying from London Southend Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the centre of Chicago. We've found flights into this airport from £574.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from London Southend Airport to Chicago on Wednesday, 21 October 2026.
      No airlines currently offer direct flights between London Southend Airport and Chicago. Most routes have one or more stops.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      In October, the average temperature is usually around 14°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.
      Currently, easyJet offers the cheapest flight tickets to Chicago.

      How to find cheap flights to Chicago from London Southend

      Looking for cheap tickets from London Southend to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

      • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from London Southend to Chicago. And with us there are no hidden fees - what you see is what you pay.
      • Compare flight deals to Chicago from London Southend from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
      • Flex your dates to find the best London Southend-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from London Southend.
      • Set up a Price Alert. You can easily track the fare of your cheap London Southend-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
      • Fly without stops. Only interested in direct flights between London Southend and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
      • Find the cheapest Business class flights from London Southend and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
      • Include nearby airports in your search. Widen your search for London Southend to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

        • Combine your flight to Chicago from London Southend with hotels and car hire

        Once you've secured your cheap flight ticket from London Southend to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


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      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.