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Cheap flights from Wales to Chicago from £196

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 19/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
28 Feb — 7 Mar1
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 29 January 2026.

Wed 25/212:25
MAN
-
ORD
2 stops34h 20m
Multiple Airlines
Wed 4/319:20
ORD
-
MAN
2 stops21h 55m
Multiple Airlines
Deal found 28/1£397
Wed 25/210:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Wed 4/319:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 28/1£402
Thu 12/310:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Mon 23/320:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 27/1£403
Thu 26/210:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Mon 2/319:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 26/1£408
Thu 19/219:15
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Mon 20/419:15
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 29/1£411
Fri 20/220:55
MAN
-
ORD
2 stops25h 50m
Scandinavian Airlines
Sat 25/419:15
ORD
-
MAN
1 stop17h 35m
Scandinavian Airlines
Deal found 29/1£414
Thu 19/219:15
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Sat 25/419:15
ORD
-
MAN
2 stops18h 15m
Scandinavian Airlines
Deal found 29/1£417
Tue 5/508:25
BRS
-
ORD
1 stop16h 50m
British Airways
Wed 13/522:25
ORD
-
BRS
1 stop14h 10m
British Airways
Deal found 27/1£494
Thu 16/408:55
BRS
-
ORD
2 stops16h 30m
Multiple Airlines
Thu 30/419:25
ORD
-
BRS
2 stops21h 10m
Multiple Airlines
Deal found 26/1£499
Thu 16/408:25
BRS
-
ORD
1 stop11h 35m
British Airways
Thu 30/415:45
ORD
-
BRS
1 stop10h 10m
British Airways
Deal found 26/1£513
Thu 12/313:30
MAN
-
MDW
1 stop14h 01m
Virgin Atlantic
Mon 23/310:45
MDW
-
MAN
2 stops14h 45m
Virgin Atlantic
Deal found 27/1£519
Tue 5/508:20
BRS
-
ORD
2 stops15h 55m
Multiple Airlines
Wed 13/515:45
ORD
-
BRS
1 stop10h 45m
Multiple Airlines
Deal found 27/1£522

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 29 January 2026.

Round-trip from

£397

One-way from

£196
25/2-4/3
  • 25/2-4/3
  • 4 total stops
  • 56h 15m total
  • Wales to Chicago
Search Deals
19/4
  • 19/4
  • 2 total stops
  • 41h 40m 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 29 January 2026.
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

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 26/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 2/3

19:20-18:35

1 stop17h 15m

£408

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 25/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 25/4

19:15-18:50

1 stop17h 35m

£411

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 21/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 20/4

19:15-08:55

1 stop31h 40m

£411

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 20/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 20/4

19:15-18:30

1 stop17h 15m

£411

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 20/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Sat 25/4

19:15-08:55

1 stop31h 40m

£411

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 5/5

08:25-19:15

1 stop16h 50m

Chicago O'Hare Intl

Wed 13/5

22:25-18:35

1 stop14h 10m

£494

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 16/4

08:55-19:25

2 stops16h 30m

Chicago O'Hare Intl

Thu 30/4

19:25-22:35

2 stops21h 10m

£499

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Thu 12/3

13:30-22:31

1 stop14h 01m

Chicago Midway

Mon 23/3

10:45-06:30

2 stops14h 45m

£519

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 5/5

08:20-18:15

2 stops15h 55m

Chicago O'Hare Intl

Wed 13/5

15:45-08:30

1 stop10h 45m

£522

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 15/4

10:50-22:28

1 stop17h 38m

Chicago Midway

Sun 26/4

09:27-07:15

2 stops15h 48m

£536

Flights are sorted by cheapest return flights first.

Deals found on 28/1

Showing 1-10 of 60 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?

    Scandinavian Airlines, British Airways, and Virgin Atlantic can get you from Wales to Chicago in just under 12h 35m. Your travel time can differ by up to 4h 15m. 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.

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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Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Edinburgh to Midway flights
Manchester to Midway flights
Heathrow to St. Louis flights
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
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Glasgow Intl to Midway flights
London City to St. Louis flights
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Birmingham to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Leeds to O'Hare Intl flights
Stansted to St. Louis flights
Norwich to O'Hare Intl flights
Inverness to O'Hare Intl flights
Bristol to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Bristol to Midway flights
Liverpool to O'Hare Intl flights
Luton to St. Louis flights
Belfast City to O'Hare Intl flights
Southampton to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Heathrow to Evansville flights
Cardiff to O'Hare Intl flights
Edinburgh to St. Louis flights
Leeds to Midway flights
Manchester to St. Louis flights
Southend to O'Hare Intl flights
Heathrow to Peoria flights
London City to Midway flights
Newcastle upon Tyne to Midway flights
Exeter to O'Hare Intl flights
Glasgow Intl to St. Louis flights
Heathrow to Champaign flights
Manchester to Peoria flights
Birmingham to St. Louis flights
Gatwick to Champaign flights
Darlington to O'Hare Intl flights
Southampton to Midway flights
Edinburgh to Moline flights
Heathrow to Moline 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 29 January 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£533Average£682FlexibilityNo 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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