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Cheap flights from Wales to Chicago from £246

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 28/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
29 Apr — 6 May1
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 30 March 2026.

Tue 21/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Tue 2/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£446
Mon 20/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Tue 2/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£464
Thu 16/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Tue 2/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£465
Tue 21/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Thu 4/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£482
Tue 21/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Sat 6/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£486
Tue 21/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Sun 31/519:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£487
Wed 15/408:40
MAN
-
ORD
2 stops34h 25m
Multiple Airlines
Sat 25/419:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 28/3£498
Mon 20/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Thu 4/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£499
Thu 16/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Thu 4/619:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£501
Mon 20/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Sun 31/519:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£504
Thu 16/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Sun 31/519:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Deal found 25/3£505
Tue 12/508:20
BRS
-
ORD
1 stop11h 40m
Multiple Airlines
Tue 19/515:45
ORD
-
BRS
1 stop11h 10m
Multiple Airlines
Deal found 28/3£557

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 30 March 2026.

Round-trip from

£446

One-way from

£246
Icelandair
  • Icelandair
  • 21/4-2/6
  • 2 total stops
  • 21h 25m total
  • Wales to Chicago
Search Deals
28/4
  • 28/4
  • 2 total stops
  • 47h 15m 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 30 March 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
Fastest return journey

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 12/5

08:20-14:00

1 stop11h 40m

Chicago O'Hare Intl

Tue 19/5

15:45-08:55

1 stop11h 10m

£557

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 4/5

08:20-23:15

3 stops44h 55m

Chicago O'Hare Intl

Tue 12/5

09:55-10:10

2 stops18h 15m

£606

BristolChicago

BRS - ORD

BRSORD

Bristol

Wed 19/8

07:55-11:50

2 stops33h 55m

Chicago O'Hare Intl

Wed 2/9

15:45-14:35

1 stop16h 50m

£674

BristolChicago

BRS - MDW

BRSMDW

Bristol

Mon 4/5

06:15-18:36

2 stops18h 21m

Chicago Midway

Tue 12/5

18:36-17:00

2 stops16h 24m

£679

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 24/9

23:30-09:40

1 stop16h 10m

Chicago O'Hare Intl

Mon 28/9

11:25-12:05

1 stop18h 40m

£679

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 23/6

23:30-09:40

1 stop16h 10m

Chicago O'Hare Intl

Thu 9/7

11:25-09:35

1 stop16h 10m

£712

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 13/5

06:05-19:55

1 stop19h 50m

Chicago O'Hare Intl

Wed 20/5

14:55-10:10

1 stop13h 15m

£718

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 27/4

13:00-08:47

2 stops25h 47m

Chicago Midway

Mon 4/5

14:12-14:00

2 stops17h 48m

£718

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 16/9

05:55-16:27

2 stops16h 32m

Chicago Midway

Wed 23/9

10:35-08:15

2 stops15h 40m

£722

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 11/5

06:00-20:08

2 stops20h 08m

Chicago O'Hare Intl

Mon 18/5

16:25-17:10

2 stops18h 45m

£725

Flights are sorted by cheapest return flights first.

Deals found on 25/3

Showing 1-10 of 59 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?

    Delta, Turkish Airlines, and United Airlines can get you from Wales to Chicago in just under 16h 10m. Your travel time can differ by up to 3h 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 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
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Manchester to O'Hare Intl flights
Gatwick to St. Louis flights
Manchester to Midway flights
Stansted to St. Louis flights
Birmingham to Midway flights
London City to St. Louis flights
Leeds to O'Hare Intl flights
Edinburgh to Midway flights
Glasgow Intl to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Southampton to O'Hare Intl flights
Bristol to O'Hare Intl flights
Luton to St. Louis flights
Glasgow Intl to Midway flights
Cardiff to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Heathrow to Peoria flights
Newcastle upon Tyne to Midway flights
Heathrow to Evansville flights
Manchester to St. Louis flights
Norwich to O'Hare Intl flights
Bristol to Midway flights
London City to Evansville flights
Grimsby to O'Hare Intl flights
Cardiff to Midway flights
Leeds to Midway flights
Heathrow to Champaign flights
Southend to O'Hare Intl flights
Southampton to Midway flights
Manchester to Moline flights
Heathrow to Springfield flights
London City to Peoria flights
Manchester to Peoria flights
Newquay to O'Hare Intl flights
London City to Midway flights
Gatwick to Evansville flights
Gatwick to Champaign flights
Exeter to O'Hare Intl flights
Heathrow to Moline flights
Leeds to St. Louis 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 30 March 2026.
AirlineCheapestAverageFlexibilityOn-time
KLMCheapest£554Average£710FlexibilityNo 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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