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Cheap flights from Wales to Chicago from £266

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
28 May — 4 Jun1
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 28 April 2026.

Thu 10/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 15/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/4£506
Sat 5/907:45
MAN
-
ORD
2 stops16h 05m
Multiple Airlines
Sat 19/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/4£508
Tue 19/522:45
MAN
-
ORD
3 stops26h 55m
Multiple Airlines
Tue 2/609:55
ORD
-
MAN
3 stops28h 10m
Multiple Airlines
Deal found 24/4£518
Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 6/1015:45
ORD
-
MAN
1 stop9h 55m
Multiple Airlines
Deal found 27/4£525
Thu 10/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Wed 16/921:00
ORD
-
MAN
1 stop10h 55m
Multiple Airlines
Deal found 26/4£533
Sat 5/907:45
MAN
-
ORD
2 stops16h 05m
Multiple Airlines
Sun 13/921:00
ORD
-
MAN
1 stop10h 55m
Multiple Airlines
Deal found 26/4£535
Tue 9/613:40
MAN
-
ORD
2 stops34h 35m
Multiple Airlines
Tue 16/622:25
ORD
-
MAN
3 stops31h 40m
Multiple Airlines
Deal found 24/4£536
Mon 15/607:45
MAN
-
ORD
2 stops16h 30m
Multiple Airlines
Thu 17/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/4£538
Mon 15/607:45
MAN
-
ORD
2 stops16h 30m
Multiple Airlines
Sat 19/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/4£539
Sun 14/614:35
MAN
-
ORD
2 stops29h 55m
Multiple Airlines
Sun 20/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/4£540
Sun 14/614:35
MAN
-
ORD
2 stops29h 55m
Multiple Airlines
Sat 19/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/4£540
Tue 9/608:20
BRS
-
ORD
1 stop11h 40m
Multiple Airlines
Tue 16/621:00
ORD
-
BRS
1 stop13h 35m
Multiple Airlines
Deal found 25/4£555

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 28 April 2026.

Round-trip from

£506

One-way from

£266
Icelandair
  • Icelandair
  • 10/9-15/9
  • 3 total stops
  • 27h 10m total
  • Wales to Chicago
Search Deals
17/5
  • 17/5
  • 2 total stops
  • 54h 15m 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 28 April 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

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 9/6

08:20-14:00

1 stop11h 40m

Chicago O'Hare Intl

Tue 16/6

21:00-16:35

1 stop13h 35m

£555
Fastest return journey

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 21/5

08:25-14:00

1 stop11h 35m

Chicago O'Hare Intl

Wed 3/6

21:00-16:00

1 stop13h 00m

£565

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 9/6

08:25-14:00

1 stop11h 35m

Chicago O'Hare Intl

Tue 16/6

21:00-16:00

1 stop13h 00m

£649

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 21/5

21:20-23:56

3 stops32h 36m

Chicago O'Hare Intl

Wed 3/6

09:55-14:35

2 stops22h 40m

£665

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 16/9

13:05-18:15

1 stop11h 10m

Chicago O'Hare Intl

Wed 23/9

22:25-11:40

1 stop31h 15m

£668

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 21/5

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sun 24/5

06:07-12:05

2 stops23h 58m

£695

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Tue 26/5

23:15-19:40

2 stops26h 25m

Chicago O'Hare Intl

Tue 2/6

09:55-23:05

2 stops31h 10m

£696

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Tue 26/5

11:35-09:45

1 stop28h 10m

Chicago Midway

Tue 2/6

19:13-10:15

2 stops33h 02m

£709

BristolChicago

BRS - ORD

BRSORD

Bristol

Fri 16/10

18:20-19:15

2 stops30h 55m

Chicago O'Hare Intl

Fri 30/10

16:55-07:55

1 stop10h 00m

£713

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 22/5

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Fri 29/5

19:15-11:45

2 stops34h 30m

£719

Flights are sorted by cheapest return flights first.

Deals found on 26/4

Showing 1-10 of 50 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?

    Aer Lingus, Icelandair, and Scandinavian Airlines can get you from Wales to Chicago in just under 11h 10m. Your travel time can differ by up to 1h 25m. 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 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
Stansted to O'Hare Intl flights
Heathrow to Midway flights
London City to O'Hare Intl flights
Luton to O'Hare Intl flights
Manchester to O'Hare Intl flights
Heathrow to St. Louis flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Birmingham to Midway flights
Stansted to St. Louis flights
Gatwick to St. Louis flights
Edinburgh to Midway flights
Glasgow Intl to Midway flights
Leeds to O'Hare Intl flights
London City to St. Louis flights
Cardiff to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Luton to St. Louis flights
Bristol to O'Hare Intl flights
Manchester to St. Louis flights
Norwich to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Leeds to Midway flights
Southampton to O'Hare Intl flights
Bristol to Midway flights
Newcastle upon Tyne to Midway flights
Belfast Intl to O'Hare Intl flights
Southend to O'Hare Intl flights
Newcastle upon Tyne to St. Louis flights
Cardiff to Midway flights
Edinburgh to St. Louis flights
Belfast City to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Heathrow to Moline flights
London City to Midway flights
Inverness to O'Hare Intl flights
London City to Peoria flights
Newquay to O'Hare Intl flights
Heathrow to Peoria flights
Manchester to Peoria flights
Heathrow to Champaign flights
Exeter to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Edinburgh to Moline flights
Southampton to Midway 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 28 April 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£630Average£695FlexibilityNo 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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