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Cheap flights from Wales to Chicago from £258

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
28 Jun — 5 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 29 May 2026.

Thu 9/706:00
MAN
-
ORD
2 stops19h 52m
Multiple Airlines
Sat 25/722:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 26/5£490
Thu 10/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Tue 22/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/5£490
Thu 24/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Sun 11/1019:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 28/5£500
Wed 8/722:25
MAN
-
ORD
2 stops24h 32m
Multiple Airlines
Wed 15/722:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Deal found 28/5£502
Thu 1/1006:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Mon 2/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 27/5£509
Sat 5/907:45
MAN
-
ORD
2 stops16h 05m
Multiple Airlines
Sat 19/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 28/5£512
Mon 23/1110:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Tue 1/1219:15
ORD
-
MAN
1 stop17h 20m
Scandinavian Airlines
Deal found 24/5£515
Wed 7/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Wed 14/1019:15
ORD
-
MAN
2 stops19h 15m
Scandinavian Airlines
Deal found 25/5£518
Thu 24/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Wed 7/1015:45
ORD
-
MAN
1 stop9h 55m
Multiple Airlines
Deal found 28/5£524
Mon 5/1009:35
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 18/1019:15
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 25/5£525
Sat 15/807:30
CWL
-
ORD
3 stops18h 35m
Multiple Airlines
Sun 23/815:45
ORD
-
CWL
2 stops24h 00m
Multiple Airlines
Deal found 28/5£636
Wed 15/708:35
BRS
-
ORD
2 stops34h 05m
Multiple Airlines
Tue 21/722:25
ORD
-
BRS
2 stops18h 45m
Multiple Airlines
Deal found 27/5£642

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 29 May 2026.

Round-trip from

£490

One-way from

£258
Icelandair
  • Icelandair
  • 9/7-25/7
  • 3 total stops
  • 51h 07m 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 29 May 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 23/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 28/11

19:15-09:30

1 stop32h 15m

£610

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 25/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 29/11

19:15-18:35

1 stop17h 20m

£610

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 25/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 28/11

19:15-09:30

1 stop32h 15m

£610

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 25/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 30/11

19:15-18:35

1 stop17h 20m

£610

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 16/9

21:10-16:10

2 stops25h 00m

Chicago O'Hare Intl

Wed 23/9

19:15-18:30

1 stop17h 15m

£626

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 24/11

17:10-15:30

1 stop28h 20m

Chicago O'Hare Intl

Fri 4/12

20:10-16:15

1 stop14h 05m

£636

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 21/8

19:10-16:10

1 stop27h 00m

Chicago O'Hare Intl

Sat 29/8

19:15-08:55

1 stop31h 40m

£677

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 8/6

12:45-16:10

2 stops33h 25m

Chicago O'Hare Intl

Mon 24/8

19:15-19:45

2 stops18h 30m

£686

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

10:40-22:25

1 stop17h 45m

Chicago Midway

Wed 23/9

13:00-07:15

1 stop12h 15m

£731

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 17/6

09:35-16:10

1 stop12h 35m

Chicago O'Hare Intl

Fri 26/6

19:15-18:30

1 stop17h 15m

£750

Flights are sorted by cheapest return flights first.

Deals found on 29/5

Showing 1-10 of 41 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 17h 07m. Your travel time can differ by up to 32h 43m. 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
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
Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Gatwick to St. Louis flights
Gatwick to Midway flights
Stansted to St. Louis 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
Edinburgh to Midway flights
Luton to St. Louis flights
Birmingham to Midway flights
Belfast Intl to O'Hare Intl flights
Leeds to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Norwich to O'Hare Intl flights
Edinburgh to St. Louis flights
Manchester to St. Louis flights
Heathrow to Springfield flights
Bristol to O'Hare Intl flights
Southend to O'Hare Intl flights
Glasgow Intl to St. Louis flights
Birmingham to St. Louis flights
Manchester to Peoria flights
Leeds to Midway flights
Bristol to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Grimsby to O'Hare Intl flights
Southampton to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Heathrow to Peoria flights
Newcastle upon Tyne to Midway flights
Newquay to O'Hare Intl flights
Liverpool to St. Louis flights
Newcastle upon Tyne to St. Louis flights
Darlington to Midway flights
London City to Midway flights
Gatwick to Champaign flights
Exeter to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Heathrow 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 29 May 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£698Average£701FlexibilityNo 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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