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Cheap flights from Wales to Chicago from £305

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 31/8. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
28 Jul — 4 Aug1
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 June 2026.

Wed 7/1013:05
MAN
-
ORD
1 stop14h 20m
Icelandair
Wed 14/1019:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 27/6£477
Thu 29/1008:00
MAN
-
ORD
2 stops15h 20m
Multiple Airlines
Thu 12/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/6£489
Mon 7/922:35
MAN
-
ORD
2 stops27h 13m
Multiple Airlines
Wed 23/922:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 28/6£490
Thu 20/806:00
MAN
-
ORD
2 stops16h 57m
Multiple Airlines
Mon 31/819:25
ORD
-
MAN
2 stops20h 55m
Multiple Airlines
Deal found 27/6£492
Tue 18/807:30
MAN
-
ORD
2 stops18h 22m
Multiple Airlines
Mon 31/819:25
ORD
-
MAN
2 stops20h 55m
Multiple Airlines
Deal found 26/6£494
Tue 18/807:30
MAN
-
ORD
2 stops18h 22m
Multiple Airlines
Sat 29/819:25
ORD
-
MAN
2 stops20h 35m
Multiple Airlines
Deal found 27/6£498
Tue 8/913:50
MAN
-
ORD
2 stops34h 00m
Multiple Airlines
Sun 13/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 26/6£500
Thu 10/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Thu 24/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 28/6£510
Mon 9/1107:45
MAN
-
ORD
2 stops15h 35m
Multiple Airlines
Sun 15/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/6£510
Sat 22/822:20
BRS
-
ORD
2 stops24h 37m
Multiple Airlines
Mon 7/922:25
ORD
-
BRS
2 stops18h 35m
Multiple Airlines
Deal found 27/6£514
Thu 20/813:00
MAN
-
MDW
1 stop15h 36m
Virgin Atlantic
Thu 3/912:46
MDW
-
MAN
1 stop14h 04m
Virgin Atlantic
Deal found 23/6£515
Wed 16/920:20
BRS
-
ORD
2 stops31h 15m
Multiple Airlines
Mon 5/1021:00
ORD
-
BRS
1 stop11h 25m
Multiple Airlines
Deal found 27/6£529

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 June 2026.

Round-trip from

£467

One-way from

£305
20/8-31/8
  • 20/8-31/8
  • 5 total stops
  • 53h 55m total
  • Wales to Chicago
Search Deals
31/8
  • 31/8
  • 3 total stops
  • 40h 35m 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 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

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 16/11

19:15-12:15

2 stops35h 00m

£551

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

£564

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 3/9

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Wed 9/9

19:15-18:30

1 stop17h 15m

£618

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 15/9

11:40-19:15

1 stop13h 35m

Chicago O'Hare Intl

Wed 30/9

19:05-15:30

1 stop14h 25m

£625

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 6/8

06:00-18:15

2 stops18h 15m

Chicago O'Hare Intl

Sun 9/8

19:25-22:10

2 stops20h 45m

£626

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 7/9

10:35-18:15

1 stop13h 40m

Chicago O'Hare Intl

Mon 14/9

16:05-17:10

1 stop19h 05m

£637

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 14/9

06:15-14:30

1 stop14h 15m

Chicago O'Hare Intl

Thu 1/10

16:20-17:00

1 stop18h 40m

£648

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 15/9

19:50-16:10

2 stops26h 20m

Chicago O'Hare Intl

Wed 30/9

19:15-20:30

2 stops19h 15m

£648

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 3/9

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sun 6/9

19:15-18:30

1 stop17h 15m

£648

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 30/8

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Fri 11/9

19:15-19:30

1 stop18h 15m

£648

Flights are sorted by cheapest return flights first.

Deals found on 25/6

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, British Airways, and KLM can get you from Wales to Chicago in just under 12h 35m. Your travel time can differ by up to 1h 40m. 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
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
Edinburgh to O'Hare Intl flights
Manchester to Midway flights
Gatwick to St. Louis flights
Gatwick to Midway flights
Stansted to St. Louis flights
Glasgow Intl to O'Hare Intl flights
Birmingham to O'Hare Intl flights
London City to St. Louis flights
Birmingham to Midway flights
Glasgow Intl to Midway flights
Edinburgh to Midway flights
Cardiff to O'Hare Intl flights
Luton to St. Louis flights
Southampton to O'Hare Intl flights
Bristol to O'Hare Intl flights
Cardiff to Midway flights
Heathrow to Evansville flights
Leeds to O'Hare Intl flights
Inverness to O'Hare Intl flights
London City to Midway flights
Glasgow Intl to St. Louis flights
Belfast Intl to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Southend to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Bristol to Midway flights
Edinburgh to St. Louis flights
Manchester to St. Louis flights
Heathrow to Champaign flights
Heathrow to Peoria flights
Leeds to Midway flights
Southampton to Midway flights
Heathrow to Moline flights
Darlington to Midway flights
Newcastle upon Tyne to Midway flights
Belfast City to O'Hare Intl flights
Manchester to Peoria flights
Grimsby to O'Hare Intl flights
Gatwick to Champaign flights
Newquay to O'Hare Intl flights
Exeter to O'Hare Intl 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 28 June 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£709Average£713FlexibilityNo cancel feeOn-time75%
Search KLM flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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