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Cheap flights from Wales to Chicago from £256

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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
13 Jul — 20 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 13 June 2026.

Sun 30/822:25
MAN
-
ORD
2 stops27h 27m
Multiple Airlines
Sat 5/922:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 10/6£503
Thu 1/1006:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Mon 5/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 10/6£507
Tue 1/907:30
MAN
-
ORD
2 stops20h 05m
Multiple Airlines
Thu 3/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 10/6£517
Mon 31/818:00
MAN
-
ORD
2 stops29h 50m
Multiple Airlines
Sun 6/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 8/6£518
Sun 6/920:25
MAN
-
ORD
2 stops28h 50m
Multiple Airlines
Sat 12/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 12/6£518
Thu 3/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 8/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 10/6£519
Thu 8/1017:55
MAN
-
ORD
1 stop28h 05m
TAP AIR PORTUGAL
Wed 14/1018:00
ORD
-
MAN
1 stop34h 10m
TAP AIR PORTUGAL
Deal found 9/6£523
Tue 1/913:50
MAN
-
ORD
2 stops34h 00m
Multiple Airlines
Sun 6/921:00
ORD
-
MAN
1 stop10h 55m
Multiple Airlines
Deal found 8/6£524
Mon 2/1120:55
MAN
-
ORD
2 stops25h 50m
Scandinavian Airlines
Mon 1/219:15
ORD
-
MAN
1 stop17h 20m
Scandinavian Airlines
Deal found 10/6£525
Fri 21/823:00
MAN
-
ORD
2 stops23h 57m
Multiple Airlines
Sat 5/922:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 9/6£526
Thu 27/808:55
BRS
-
ORD
2 stops15h 20m
Multiple Airlines
Sun 6/919:25
ORD
-
BRS
2 stops21h 30m
Multiple Airlines
Deal found 10/6£537
Tue 1/921:30
MAN
-
MDW
3 stops26h 31m
Multiple Airlines
Sun 6/916:52
MDW
-
MAN
3 stops24h 48m
Multiple Airlines
Deal found 8/6£573

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 13 June 2026.

Round-trip from

£503

One-way from

£256
Icelandair
  • Icelandair
  • 30/8-5/9
  • 3 total stops
  • 58h 42m total
  • Wales to Chicago
Search Deals
9/9
  • 9/9
  • 2 total stops
  • 31h 50m 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 13 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

Mon 5/10

20:25-16:10

2 stops25h 45m

Chicago O'Hare Intl

Sun 18/10

19:15-18:30

1 stop17h 15m

£566

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 15/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Tue 20/10

19:15-20:30

2 stops19h 15m

£566

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 27/8

12:00-16:10

3 stops34h 10m

Chicago O'Hare Intl

Sun 6/9

19:15-22:55

3 stops21h 40m

£570

BristolChicago

BRS - ORD

BRSORD

Bristol

Sun 13/9

17:20-21:20

2 stops34h 00m

Chicago O'Hare Intl

Wed 23/9

15:45-08:30

1 stop10h 45m

£599

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 16/9

13:05-21:25

1 stop14h 20m

Chicago O'Hare Intl

Wed 23/9

22:25-11:40

1 stop31h 15m

£602

BristolChicago

BRS - ORD

BRSORD

Bristol

Sun 13/9

17:35-14:30

1 stop26h 55m

Chicago O'Hare Intl

Tue 22/9

16:20-08:50

1 stop10h 30m

£608
Fastest return journey

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 23/11

11:55-17:20

1 stop11h 25m

Chicago O'Hare Intl

Fri 27/11

18:30-10:45

1 stop10h 15m

£611

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Tue 25/8

23:15-19:52

2 stops26h 37m

Chicago O'Hare Intl

Mon 31/8

19:25-22:50

2 stops21h 25m

£612

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 28/7

08:20-18:15

2 stops15h 55m

Chicago O'Hare Intl

Tue 4/8

19:25-22:55

2 stops21h 30m

£615

BristolChicago

BRS - ORD

BRSORD

Bristol

Sat 14/11

16:00-14:00

1 stop28h 00m

Chicago O'Hare Intl

Tue 17/11

18:33-16:00

2 stops39h 27m

£624

Flights are sorted by cheapest return flights first.

Deals found on 9/6

Showing 1-10 of 46 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, KLM, and Delta can get you from Wales to Chicago in just under 16h 35m. Your travel time can differ by up to 10h 20m. The distance from Wales to Chicago is about 3858 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
London City 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
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
Gatwick to St. Louis flights
Edinburgh to O'Hare Intl flights
Birmingham to Midway flights
Stansted to St. Louis flights
London City to St. Louis flights
Edinburgh to Midway flights
Manchester to St. Louis flights
Leeds to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Southampton to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
Luton to St. Louis flights
Belfast Intl to O'Hare Intl flights
Glasgow Intl to Midway flights
Bristol to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Leeds to Midway flights
Heathrow to Moline flights
Edinburgh to St. Louis flights
Manchester to Peoria flights
Bristol to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Southampton to Midway flights
Glasgow Intl to St. Louis flights
Birmingham to St. Louis flights
Heathrow to Peoria flights
Newquay to O'Hare Intl flights
Darlington to O'Hare Intl flights
Manchester to Moline flights
Darlington to Midway flights
Newcastle upon Tyne to Midway flights
London City to Midway flights
Exeter to O'Hare Intl flights
Cardiff to Midway flights
Heathrow to Evansville flights
Gatwick to Champaign flights
Heathrow to Springfield flights
London City 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 13 June 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£698Average£702FlexibilityNo 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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