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Cheap flights from Wales to Chicago from £245

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
6 Jul — 13 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 6 June 2026.

Thu 3/922:55
MAN
-
ORD
2 stops28h 40m
Multiple Airlines
Mon 5/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 3/6£465
Thu 2/722:25
MAN
-
ORD
2 stops24h 32m
Multiple Airlines
Sat 18/722:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 2/6£487
Fri 21/823:00
MAN
-
ORD
3 stops27h 05m
Multiple Airlines
Sat 5/922:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 4/6£498
Thu 10/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 22/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 1/6£507
Thu 24/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Wed 30/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 4/6£508
Thu 3/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Sat 3/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 1/6£509
Thu 17/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Sun 27/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 5/6£514
Fri 4/906:15
MAN
-
ORD
2 stops21h 20m
Multiple Airlines
Mon 5/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 1/6£522
Thu 24/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Mon 28/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 2/6£528
Sat 5/907:45
MAN
-
ORD
2 stops16h 05m
Multiple Airlines
Mon 5/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 1/6£529
Tue 30/607:30
MAN
-
MDW
2 stops32h 10m
Multiple Airlines
Tue 7/715:20
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 2/6£627
Mon 13/712:25
BRS
-
ORD
1 stop12h 50m
Aer Lingus
Tue 28/715:45
ORD
-
BRS
1 stop10h 10m
Aer Lingus
Deal found 4/6£633

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 6 June 2026.

Round-trip from

£465

One-way from

£245
Icelandair
  • Icelandair
  • 3/9-5/10
  • 3 total stops
  • 38h 55m total
  • Wales to Chicago
Search Deals
8/9
  • 8/9
  • 2 total stops
  • 28h 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 6 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 15/10

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Tue 20/10

19:15-20:30

2 stops19h 15m

£570

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 28/10

10:10-17:45

1 stop12h 35m

Chicago O'Hare Intl

Wed 11/11

19:15-12:15

2 stops35h 00m

£572

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 13/7

12:25-19:15

1 stop12h 50m

Chicago O'Hare Intl

Thu 30/7

21:00-16:00

1 stop13h 00m

£639

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 16/9

09:35-22:22

2 stops18h 47m

Chicago O'Hare Intl

Wed 23/9

19:15-18:30

1 stop17h 15m

£648

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

£657

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 13/7

14:55-14:00

1 stop29h 05m

Chicago O'Hare Intl

Tue 28/7

15:45-07:55

1 stop10h 10m

£661

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 2/7

22:50-13:09

3 stops44h 19m

Chicago Midway

Mon 6/7

09:54-10:15

2 stops18h 21m

£668

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 16/9

09:35-22:22

2 stops18h 47m

Chicago O'Hare Intl

Sat 26/9

13:55-18:50

2 stops22h 55m

£673

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Thu 2/7

11:35-09:14

2 stops27h 39m

Chicago Midway

Mon 6/7

09:54-10:15

2 stops18h 21m

£708

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 30/6

20:55-11:29

1 stop20h 34m

Chicago O'Hare Intl

Tue 7/7

21:15-15:10

1 stop11h 55m

£716

Flights are sorted by cheapest return flights first.

Deals found on 3/6

Showing 1-10 of 54 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, Aer Lingus, and WestJet can get you from Wales to Chicago in just under 12h 35m. Your travel time can differ by up to 15h 04m. 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
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 Midway flights
Birmingham to O'Hare Intl flights
Gatwick to St. Louis flights
Edinburgh to Midway flights
Glasgow Intl to O'Hare Intl flights
Stansted to St. Louis flights
London City to St. Louis flights
Birmingham to Midway flights
Glasgow Intl to Midway flights
Leeds to O'Hare Intl flights
Bristol to O'Hare Intl flights
Bristol to Midway flights
Belfast Intl to O'Hare Intl flights
Manchester to St. Louis flights
Southend to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Leeds to Midway flights
Newcastle upon Tyne to Midway flights
Luton to St. Louis flights
Southampton to O'Hare Intl flights
London City to Midway flights
Belfast City to O'Hare Intl flights
Heathrow to Champaign flights
Southampton to Midway flights
Leeds to St. Louis flights
Inverness to O'Hare Intl flights
Edinburgh to St. Louis flights
Exeter to O'Hare Intl flights
Glasgow Intl to St. Louis flights
Cardiff to Midway flights
Liverpool to O'Hare Intl flights
Gatwick to Champaign flights
Newquay to O'Hare Intl flights
Edinburgh to Moline flights
Glasgow Intl to Moline flights
Gatwick to Evansville flights
Birmingham to St. Louis flights
Heathrow to Springfield flights
Doncaster to O'Hare Intl 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 6 June 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£699Average£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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