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Cheap flights from Wales to Chicago from £272

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
19 Jul — 26 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Wales to Chicago

Enter your travel dates to find the best prices.

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 19 June 2026.

Tue 6/1010:35
MAN
-
ORD
1 stop13h 40m
Lufthansa
Sat 14/1118:30
ORD
-
MAN
1 stop32h 10m
Lufthansa
Deal found 15/6£529
Fri 11/914:40
MAN
-
ORD
2 stops33h 35m
Multiple Airlines
Sun 20/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 15/6£536
Mon 31/807:45
MAN
-
ORD
1 stop12h 15m
Multiple Airlines
Mon 7/921:00
ORD
-
MAN
1 stop12h 30m
Multiple Airlines
Deal found 15/6£540
Wed 30/907:55
MAN
-
ORD
1 stop12h 05m
Multiple Airlines
Sun 4/1021:00
ORD
-
MAN
1 stop18h 35m
Multiple Airlines
Deal found 18/6£542
Wed 16/913:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Wed 23/922:25
ORD
-
MAN
1 stop31h 15m
Icelandair
Deal found 18/6£553
Sat 29/805:50
MAN
-
ORD
2 stops19h 25m
Multiple Airlines
Sat 5/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 15/6£554
Wed 26/815:00
MAN
-
ORD
2 stops31h 10m
Multiple Airlines
Wed 2/919:15
ORD
-
MAN
2 stops21h 15m
Multiple Airlines
Deal found 15/6£558
Wed 26/809:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Mon 31/819:15
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 15/6£558
Fri 13/1105:50
MAN
-
ORD
2 stops18h 35m
Multiple Airlines
Sat 28/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 19/6£559
Tue 25/808:20
BRS
-
ORD
2 stops14h 37m
Multiple Airlines
Thu 17/919:25
ORD
-
BRS
2 stops22h 00m
Multiple Airlines
Deal found 18/6£560
Mon 5/1012:25
BRS
-
ORD
1 stop12h 50m
British Airways
Thu 15/1015:45
ORD
-
BRS
1 stop16h 40m
British Airways
Deal found 16/6£569
Fri 2/1014:55
BRS
-
ORD
1 stop29h 05m
British Airways
Sun 18/1021:00
ORD
-
BRS
1 stop11h 25m
British Airways
Deal found 18/6£585

Find flight deals from Wales to Chicago

Keep the following information in mind while searching for Wales to Chicago flight deals. Data was last updated 19 June 2026.

Round-trip from

£529

One-way from

£272
Lufthansa
  • Lufthansa
  • 6/10-14/11
  • 2 total stops
  • 45h 50m total
  • Wales to Chicago
Search Deals
15/9
  • 15/9
  • 3 total stops
  • 36h 25m total
  • Wales to Chicago
Search Deals

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 19 June 2026.
Use the filters below to find and compare flights from Wales to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 12/11

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 16/11

19:15-12:15

2 stops35h 00m

£580

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 15/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Tue 20/10

19:15-18:30

1 stop17h 15m

£583

BristolChicago

BRS - MDW

BRSMDW

Bristol

Fri 2/10

06:15-18:11

2 stops17h 56m

Chicago Midway

Sun 18/10

12:30-08:50

2 stops14h 20m

£636

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 7/7

18:40-20:29

3 stops31h 49m

Chicago O'Hare Intl

Tue 14/7

19:25-22:55

2 stops21h 30m

£642

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 9/7

08:55-18:15

2 stops15h 20m

Chicago O'Hare Intl

Wed 22/7

19:25-22:55

2 stops21h 30m

£644

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 9/7

08:25-19:15

1 stop16h 50m

Chicago O'Hare Intl

Wed 22/7

15:45-16:00

1 stop18h 15m

£649

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Wed 1/7

23:15-22:05

3 stops28h 50m

Chicago O'Hare Intl

Wed 15/7

14:15-10:15

1 stop14h 00m

£651

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 5/10

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Sun 18/10

19:15-19:45

2 stops18h 30m

£651

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 6/9

14:25-19:15

1 stop10h 50m

Chicago O'Hare Intl

Mon 14/9

19:05-13:10

1 stop12h 05m

£662

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 8/10

10:35-18:15

1 stop13h 40m

Chicago O'Hare Intl

Mon 12/10

05:00-09:50

2 stops22h 50m

£663

Flights are sorted by cheapest return flights first.

Deals found on 14/6

Showing 1-10 of 43 resultsSorted by cheapest first
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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?

    Scandinavian Airlines, Delta, and British Airways can get you from Wales to Chicago in just under 16h 50m. Your travel time can differ by up to 10h 40m. The distance from Wales to Chicago is about 3855 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 Cardiff Wales - 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.

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.
Heathrow to O'Hare Intl flights
Gatwick to O'Hare Intl flights
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Heathrow to Midway flights
Luton to O'Hare Intl flights
Heathrow to St. Louis flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Gatwick to St. Louis flights
Gatwick to Midway flights
Stansted to St. Louis flights
Glasgow Intl to O'Hare Intl flights
Birmingham to Midway flights
Leeds to O'Hare Intl flights
London City to St. Louis flights
Edinburgh to Midway flights
Glasgow Intl to Midway flights
Manchester to St. Louis flights
Luton to St. Louis flights
Cardiff to O'Hare Intl flights
Leeds to Midway flights
Southampton to O'Hare Intl flights
Cardiff to Midway flights
Edinburgh to St. Louis flights
Liverpool to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Bristol to O'Hare Intl flights
Heathrow to Moline flights
Heathrow to Peoria flights
Belfast City to O'Hare Intl flights
Exeter to O'Hare Intl flights
London City to Midway flights
Southend to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Darlington to O'Hare Intl flights
Heathrow to Springfield flights
Manchester to Moline flights
Newcastle upon Tyne to Midway flights
Manchester to Peoria flights
Glasgow Intl to St. Louis flights
Norwich to O'Hare Intl flights
Darlington to Midway flights
Bristol to Midway flights
Gatwick to Champaign flights
Newquay to O'Hare Intl flights
Heathrow to Champaign flights
Grimsby to O'Hare Intl 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 19 June 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£707Average£710FlexibilityNo 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.

Can Cheapflights notify me if prices for flights from Wales to Chicago become cheaper?

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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