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Cheap flights from Wales to Chicago from £289

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
14 May — 21 May1
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 14 April 2026.

Tue 2/613:50
MAN
-
ORD
2 stops34h 00m
Multiple Airlines
Thu 17/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 13/4£492
Wed 27/521:25
MAN
-
ORD
2 stops26h 50m
Multiple Airlines
Wed 3/622:25
ORD
-
MAN
3 stops31h 40m
Multiple Airlines
Deal found 12/4£498
Mon 23/1106:55
MAN
-
ORD
2 stops16h 25m
Multiple Airlines
Tue 1/1218:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 10/4£502
Mon 2/1108:30
MAN
-
ORD
2 stops14h 50m
Multiple Airlines
Sat 7/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 9/4£526
Mon 23/1110:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Tue 1/1219:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 10/4£528
Thu 3/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Wed 9/921:00
ORD
-
MAN
1 stop10h 55m
Multiple Airlines
Deal found 13/4£529
Mon 2/1110:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sat 7/1119:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 9/4£530
Sat 24/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sat 31/1020:20
ORD
-
MAN
2 stops15h 25m
Scandinavian Airlines
Deal found 12/4£535
Wed 21/1019:10
MAN
-
ORD
1 stop27h 00m
Scandinavian Airlines
Mon 2/1119:20
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 10/4£537
Sun 22/1110:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 29/1119:20
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 12/4£538
Mon 20/407:20
BRS
-
ORD
1 stop12h 40m
Multiple Airlines
Mon 4/521:00
ORD
-
BRS
1 stop17h 15m
Multiple Airlines
Deal found 11/4£542
Wed 13/509:20
BRS
-
ORD
1 stop15h 55m
Multiple Airlines
Tue 19/515:45
ORD
-
BRS
1 stop11h 10m
Multiple Airlines
Deal found 13/4£558

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 14 April 2026.

Round-trip from

£492

One-way from

£289
Icelandair
  • Icelandair
  • 2/6-17/9
  • 3 total stops
  • 44h 15m total
  • Wales to Chicago
Search Deals
10/9
  • 10/9
  • 2 total stops
  • 16h 55m 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 14 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

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 10/6

07:55-21:25

2 stops19h 30m

Chicago O'Hare Intl

Mon 15/6

09:55-22:20

2 stops30h 25m

£545

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 28/5

19:10-18:38

2 stops29h 28m

Chicago O'Hare Intl

Thu 4/6

12:59-12:05

2 stops17h 06m

£621

BristolChicago

BRS - ORD

BRSORD

Bristol

Wed 26/8

11:45-14:25

1 stop32h 40m

Chicago O'Hare Intl

Wed 9/9

15:45-08:30

1 stop10h 45m

£650

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 13/6

06:50-09:00

3 stops32h 10m

Chicago O'Hare Intl

Sat 20/6

15:45-22:00

2 stops24h 15m

£718

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 25/5

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Mon 1/6

06:07-12:05

2 stops23h 58m

£724

BristolChicago

BRS - ORD

BRSORD

Bristol

Sun 24/5

14:55-16:10

2 stops31h 15m

Chicago O'Hare Intl

Sun 31/5

19:15-22:55

2 stops21h 40m

£731

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 27/5

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Wed 24/6

19:15-20:45

2 stops19h 30m

£738

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Wed 26/8

23:30-14:00

1 stop20h 30m

Chicago O'Hare Intl

Wed 9/9

15:45-22:25

1 stop24h 40m

£738

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Tue 15/9

16:15-14:25

2 stops28h 10m

Chicago O'Hare Intl

Thu 1/10

21:00-22:20

1 stop19h 20m

£753

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/10

13:00-21:45

1 stop14h 45m

Chicago Midway

Wed 14/10

09:30-08:15

2 stops16h 45m

£760

Flights are sorted by cheapest return flights first.

Deals found on 9/4

Showing 1-10 of 53 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 KLM can get you from Wales to Chicago in just under 12h 35m. Your travel time can differ by up to 14h 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 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.
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
Heathrow to St. Louis flights
Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
Gatwick to St. Louis flights
Stansted to St. Louis flights
Leeds to O'Hare Intl flights
Edinburgh to Midway flights
Glasgow Intl to O'Hare Intl flights
Birmingham to Midway flights
Glasgow Intl to Midway flights
Bristol to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Luton to St. Louis flights
Bristol to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
London City to St. Louis flights
Southampton to O'Hare Intl flights
Manchester to St. Louis flights
Cardiff to Midway flights
Belfast Intl to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Norwich to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Exeter to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Heathrow to Peoria flights
Newquay to O'Hare Intl flights
Liverpool to O'Hare Intl flights
London City to Midway flights
Inverness to O'Hare Intl flights
Manchester to Peoria flights
Heathrow to Champaign flights
Southend to O'Hare Intl flights
Southampton to Midway flights
Leeds to Midway flights
Edinburgh to St. Louis flights
Edinburgh to Moline flights
Glasgow Intl to St. Louis flights
Birmingham to St. Louis flights
Heathrow to Springfield flights
Manchester 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 14 April 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£635Average£700FlexibilityNo 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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