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Cheap flights from Wales to Chicago from £244

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
1 Sep — 8 Sep1
1 adult

Cheap flight deals from Wales to Chicago

Keep the following information in mind while searching for Wales to Chicago flight deals. Data was last updated 27 August 2025.

Round-trip from

£456

One-way from

£244
1/10-8/10
  • 1/10-8/10
  • 4 total stops
  • 55h 40m total
  • Wales to Chicago
Search Deals
15/10
  • 15/10
  • 2 total stops
  • 22h 10m total
  • Wales to Chicago
Search Deals

Find flight deals from Wales to Chicago

Cheapest flights from Wales to Chicago
Explore the most affordable flight options available from Wales to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 August 2025.

Wed 1/1008:25BRS - ORD
2 stops37h 30mMultiple Airlines
Wed 8/1015:50ORD - BRS
2 stops18h 10mMultiple Airlines
Deal found 27/8£456
Wed 24/912:40MAN - ORD
1 stop14h 35mIcelandair
Tue 7/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£460
Tue 11/1114:30MAN - ORD
2 stops30h 30mMultiple Airlines
Tue 18/1109:18ORD - MAN
3 stops23h 32mMultiple Airlines
Deal found 26/8£470
Sat 18/1011:15MAN - ORD
2 stops34h 55mScandinavian Airlines
Sat 25/1020:20ORD - MAN
2 stops18h 25mScandinavian Airlines
Deal found 26/8£474
Wed 1/1012:40MAN - ORD
1 stop14h 35mIcelandair
Sun 5/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 26/8£474
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Mon 6/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 25/8£475
Wed 5/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sun 4/119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 26/8£476
Wed 17/913:05MAN - ORD
1 stop11h 10mIcelandair
Thu 2/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 27/8£476
Thu 18/917:55MAN - ORD
1 stop28h 35mTAP AIR PORTUGAL
Sat 11/1018:15ORD - MAN
1 stop33h 50mTAP AIR PORTUGAL
Deal found 25/8£479
Fri 17/1019:10MAN - ORD
1 stop27h 00mScandinavian Airlines
Tue 28/1010:25ORD - MAN
2 stops18h 05mScandinavian Airlines
Deal found 26/8£480
Sat 4/1017:55MAN - ORD
1 stop28h 15mScandinavian Airlines
Thu 6/1119:20ORD - MAN
1 stop32h 10mScandinavian Airlines
Deal found 26/8£482
Thu 23/1010:10MAN - ORD
1 stop12h 00mScandinavian Airlines
Sun 2/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 26/8£482

Cheapflights Fare Finder

 
Customise your flight search to find flights from Wales 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, Cheapflights users made 858,174 searches. Data last updated 27 August 2025.
Use the filters below to find and compare flights from Wales to Chicago that are best for you.

Fly from

Wales

Fly to

Chicago

Route

Depart

Return

Price

BristolChicago

BRS - ORD

BRSORD

Bristol

Wed 1/10

08:25-15:55

2 stops37h 30m

Chicago O'Hare Intl

Wed 8/10

15:50-16:00

2 stops18h 10m

£456

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 24/9

12:40-21:15

1 stop14h 35m

Chicago O'Hare Intl

Tue 7/10

19:25-11:40

1 stop10h 15m

£460

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 17/9

13:05-21:15

1 stop14h 10m

Chicago O'Hare Intl

Thu 2/10

19:25-11:40

1 stop10h 15m

£475

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 17/9

13:05-18:15

1 stop11h 10m

Chicago O'Hare Intl

Mon 6/10

19:25-11:40

1 stop10h 15m

£475

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 24/9

12:40-21:15

1 stop14h 35m

Chicago O'Hare Intl

Mon 6/10

19:25-11:40

1 stop10h 15m

£475

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 5/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 4/1

19:20-12:15

2 stops34h 55m

£476

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 23/10

11:35-19:00

1 stop13h 25m

Chicago O'Hare Intl

Sat 1/11

20:40-14:35

1 stop12h 55m

£498

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 11/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Tue 18/11

17:34-10:30

1 stop10h 56m

£509

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 19/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Tue 2/12

14:00-10:10

2 stops14h 10m

£541

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 11/11

13:30-23:32

1 stop16h 02m

Chicago Midway

Tue 18/11

13:47-10:10

2 stops14h 23m

£541

Flights are sorted by cheapest return flights first.

Deals found on 25/8

Showing 1-10 of 44 results
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Best time to book a flight from Wales to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Wales with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wales to Chicago
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Wales to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wales to Chicago?

    Icelandair, Virgin Atlantic, and Delta can get you from Wales to Chicago in just under 14h 35m. Your travel time can differ by up to 1h 27m. The distance from Wales to Chicago is about 3812 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the most popular routes from Wales to Chicago?

    While some choose either Manchester - Chicago Midway or Bristol - Chicago O'Hare Intl, Manchester - Chicago O'Hare Intl is the most popular route from Wales to Chicago.

  • Can I find deals for flights from Wales to Chicago that include hotel bookings?

    Yes. In addition to deals on Wales to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Wales to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wales to Chicago.

  • Can I find deals for business class flights from Wales to Chicago?

    Yes. Cheapflights offers flight deals from Wales to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wales to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Wales to Chicago (average of £595). Flying from Wales to Chicago in July is currently the most expensive (average of £843). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Wales to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Heathrow to Midway flights
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London City to Midway flights
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Manchester to St. Louis flights
Heathrow to Peoria flights
Edinburgh to St. Louis flights
Newcastle upon Tyne to St. Louis flights
Stansted to St. Louis flights
Luton to St. Louis flights
Norwich to O'Hare Intl flights
London City to Peoria flights
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Heathrow to Springfield flights
Bristol to Midway flights
Southend to O'Hare Intl flights
Newquay to O'Hare Intl flights
Cardiff to Midway flights
Glasgow Intl to St. Louis flights
Gatwick to Evansville flights
Cardiff to O'Hare Intl flights
Exeter to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Leeds to Midway flights
Leeds to St. Louis flights
London City to Evansville flights

Top airline flying from Wales to Chicago

Discover the top airline that operate flights from Wales to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 27 August 2025.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£546Average£678FlexibilityNo cancel feeOn-time75%
Search KLM flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Wales to Chicago?

Deals for Wales to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Wales to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Wales to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Wales to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Wales to Chicago flexibly with Cheapflights today.

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Of course! You can now track prices for flights from Wales to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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