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Cheap flights from Wales to Chicago from £257

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 13/10. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
16 Sep — 23 Sep1
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 17 August 2026.

Thu 3/919:20 -
2 stops32h 05m
Tue 8/922:25 -
2 stops18h 10m
Deal found 13/8£503
Wed 7/1013:05 -
1 stop14h 20m
Sat 24/1019:30 -
1 stop10h 15m
Deal found 13/8£507
Tue 6/1013:50 -
2 stops34h 00m
Tue 27/1019:30 -
1 stop10h 15m
Deal found 13/8£507
Wed 9/913:50 -
1 stop11h 25m
Sun 13/915:45 -
1 stop18h 55m
Deal found 15/8£508
Sat 19/912:25 -
1 stop12h 50m
Mon 5/1015:45 -
1 stop16h 40m
Deal found 14/8£508
Thu 1/1008:25 -
1 stop11h 35m
Thu 8/1015:45 -
1 stop10h 20m
Deal found 17/8£510
Tue 13/1016:30 -
2 stops32h 45m
Tue 20/1019:25 -
1 stop10h 15m
Deal found 14/8£513
Mon 28/912:05 -
1 stop13h 10m
Sat 3/1015:45 -
1 stop10h 55m
Deal found 13/8£514
Sat 26/907:30 -
1 stop12h 30m
Sat 3/1021:00 -
1 stop18h 20m
Deal found 12/8£517
Thu 29/1008:05 -
1 stop11h 55m
Sat 7/1115:55 -
1 stop9h 40m
Deal found 17/8£518
Thu 1/1013:05 -
1 stop11h 10m
Mon 5/1019:25 -
1 stop10h 15m
Deal found 13/8£522
Thu 12/1111:55 -
1 stop11h 25m
Fri 27/1118:30 -
1 stop10h 15m
Deal found 12/8£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 17 August 2026.

Round-trip from

£503

One-way from

£257
3/9-8/9
  • 3/9-8/9
  • 4 total stops
  • 50h 15m total
  • Wales to Chicago
Search Deals
13/10
  • 13/10
  • 3 total stops
  • 36h 25m 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 17 August 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 Bristol - ORD Chicago O'Hare Intl

BRSORD

Bristol

Thu 1/10

08:25-14:00

1 stop11h 35m

Chicago O'Hare Intl

Thu 8/10

15:45-08:05

1 stop10h 20m

£510

BristolChicago

BRS Bristol - ORD Chicago O'Hare Intl

BRSORD

Bristol

Thu 24/9

11:45-16:00

2 stops34h 15m

Chicago O'Hare Intl

Wed 30/9

18:00-21:55

2 stops21h 55m

£528

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Thu 12/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Fri 27/11

19:15-08:40

2 stops31h 25m

£550

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Sat 17/10

10:40-16:10

2 stops35h 30m

Chicago O'Hare Intl

Sat 24/10

19:15-20:45

2 stops19h 30m

£572

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Mon 5/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Sun 18/10

19:15-18:30

1 stop17h 15m

£584

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Wed 9/9

12:45-16:10

2 stops33h 25m

Chicago O'Hare Intl

Sun 13/9

19:15-19:45

2 stops18h 30m

£589

ManchesterChicago

MAN Manchester - ORD Chicago O'Hare Intl

MANORD

Manchester

Wed 16/9

12:45-16:10

2 stops33h 25m

Chicago O'Hare Intl

Wed 23/9

19:15-09:40

2 stops32h 25m

£592

BristolChicago

BRS Bristol - ORD Chicago O'Hare Intl

BRSORD

Bristol

Sun 22/11

20:25-14:55

2 stops24h 30m

Chicago O'Hare Intl

Sun 29/11

20:10-14:25

1 stop12h 15m

£595

CardiffChicago

CWL Cardiff Wales - ORD Chicago O'Hare Intl

CWLORD

Cardiff Wales

Sat 26/9

07:30-19:15

1 stop17h 45m

Chicago O'Hare Intl

Sat 3/10

15:45-09:15

2 stops35h 30m

£603

BristolChicago

BRS Bristol - ORD Chicago O'Hare Intl

BRSORD

Bristol

Wed 2/9

08:25-14:00

1 stop11h 35m

Chicago O'Hare Intl

Sat 12/9

15:45-07:55

1 stop10h 10m

£605

Flights are sorted by cheapest return flights first.

Deals found on 15/8

Showing 1-10 of 52 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, Scandinavian Airlines, and KLM can get you from Wales to Chicago in just under 12h 50m. Your travel time can differ by up to 21h. The distance from Wales to Chicago is about 3855 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
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Heathrow to Midway flights
Luton to O'Hare Intl flights
Heathrow to St. Louis flights
Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Gatwick to Midway flights
Gatwick to St. Louis flights
Manchester to Midway flights
Stansted to St. Louis flights
Edinburgh to Midway flights
London City to St. Louis flights
Glasgow Intl to O'Hare Intl flights
Birmingham to O'Hare Intl flights
Glasgow Intl to Midway flights
Manchester to St. Louis flights
Luton to St. Louis flights
Newcastle upon Tyne to O'Hare Intl flights
Birmingham to Midway flights
Bristol to O'Hare Intl flights
Edinburgh to St. Louis flights
Southampton to O'Hare Intl flights
Southend to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Heathrow to Springfield flights
Birmingham to St. Louis flights
Leeds to O'Hare Intl flights
Cardiff to Midway flights
Liverpool to O'Hare Intl flights
Cardiff to O'Hare Intl flights
London City to Midway flights
Inverness to O'Hare Intl flights
Manchester to Peoria flights
Belfast City to O'Hare Intl flights
Heathrow to Moline flights
Heathrow to Peoria flights
Newquay to O'Hare Intl flights
Bristol to Midway flights
Glasgow Intl to St. Louis flights
Heathrow to Champaign flights
Darlington to Midway flights
Darlington to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Southampton to Midway flights
Edinburgh to Moline flights
Manchester to Moline flights
Newcastle upon Tyne 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 17 August 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£692Average£695FlexibilityNo 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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