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Cheap flights from Chicago to Wales from £161

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 25/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CWL
12 Jul — 19 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Wales

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Wales
Explore the most affordable flight options available from Chicago to Wales. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2026.

Fri 4/911:45
ORD
-
CWL
1 stop16h 30m
Multiple Airlines
Mon 7/911:35
CWL
-
ORD
1 stop33h 00m
Multiple Airlines
Deal found 7/6£502
Sun 2/810:20
MDW
-
CWL
1 stop17h 55m
Multiple Airlines
Tue 18/823:15
CWL
-
MDW
2 stops40h 25m
Multiple Airlines
Deal found 11/6£527
Sun 2/814:15
ORD
-
CWL
1 stop14h 00m
Multiple Airlines
Tue 18/823:15
CWL
-
ORD
2 stops23h 42m
Multiple Airlines
Deal found 11/6£534
Sun 1/1118:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Sun 15/1111:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Deal found 9/6£562
Sat 3/1019:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Sun 11/1013:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Deal found 10/6£563
Wed 2/915:40
ORD
-
MAN
2 stops19h 05m
Multiple Airlines
Tue 8/922:45
MAN
-
ORD
2 stops25h 30m
Multiple Airlines
Deal found 10/6£566
Wed 18/1118:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Tue 1/1211:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Deal found 9/6£567
Sat 14/1118:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Mon 30/1111:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Deal found 9/6£567
Mon 23/1118:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Mon 30/1111:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Deal found 8/6£568
Fri 20/1118:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Tue 1/1206:00
MAN
-
ORD
2 stops17h 20m
Multiple Airlines
Deal found 9/6£573
Fri 3/710:25
MDW
-
CWL
1 stop17h 50m
Multiple Airlines
Mon 6/711:35
CWL
-
MDW
1 stop28h 05m
Multiple Airlines
Deal found 7/6£573
Mon 7/921:00
ORD
-
MAN
1 stop18h 15m
Multiple Airlines
Thu 10/922:55
MAN
-
ORD
1 stop21h 05m
Multiple Airlines
Deal found 11/6£574

Find flight deals from Chicago to Wales

Keep the following information in mind while searching for Chicago to Wales flight deals. Data was last updated 12 June 2026.

Round-trip from

£502

One-way from

£161
4/9-7/9
  • 4/9-7/9
  • 2 total stops
  • 49h 30m total
  • Chicago to Wales
Search Deals
Icelandair
  • Icelandair
  • 25/7
  • 1 total stop
  • 10h 15m total
  • Chicago to Wales
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Chicago to Wales 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 12 June 2026.
Use the filters below to find and compare flights from Chicago to Wales that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoCardiff

MDW - CWL

MDWCWL

Chicago Midway

Sun 2/8

10:20-10:15

1 stop17h 55m

Cardiff Wales

Tue 18/8

23:15-09:40

2 stops40h 25m

£527

ChicagoCardiff

ORD - CWL

ORDCWL

Chicago O'Hare Intl

Sun 2/8

08:45-10:15

2 stops19h 30m

Cardiff Wales

Tue 18/8

23:15-16:57

2 stops23h 42m

£546

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Sat 14/11

18:30-10:45

1 stop10h 15m

Manchester

Mon 30/11

11:55-17:20

1 stop11h 25m

£567

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Mon 16/11

18:30-10:45

1 stop10h 15m

Manchester

Fri 4/12

11:35-17:20

1 stop11h 45m

£579

ChicagoCardiff

ORD - CWL

ORDCWL

Chicago O'Hare Intl

Thu 17/9

15:45-22:20

2 stops24h 35m

Cardiff Wales

Thu 24/9

22:50-16:58

2 stops24h 08m

£605

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Mon 9/11

19:15-09:30

1 stop32h 15m

Manchester

Thu 12/11

10:10-16:45

1 stop12h 35m

£609

ChicagoCardiff

ORD - CWL

ORDCWL

Chicago O'Hare Intl

Fri 4/9

15:20-10:15

1 stop12h 55m

Cardiff Wales

Mon 7/9

22:10-16:58

2 stops24h 48m

£620

ChicagoManchester

MDW - MAN

MDWMAN

Chicago Midway

Tue 17/11

13:05-10:30

1 stop15h 25m

Manchester

Fri 4/12

13:25-22:10

1 stop14h 45m

£650

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Fri 4/9

19:15-11:45

2 stops34h 30m

Manchester

Sun 20/12

20:25-16:45

2 stops26h 20m

£671
Fastest return journey

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Sat 1/8

19:25-11:40

1 stop10h 15m

Manchester

Wed 12/8

13:05-18:15

1 stop11h 10m

£681

Flights are sorted by cheapest return flights first.

Deals found on 12/6

Showing 1-10 of 48 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Wales

Have a flexible travel schedule? Discover the best time to fly to Wales from Chicago 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 Chicago to Wales
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 Chicago to Wales. 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 Chicago to Wales?

    Airlines like Icelandair, Scandinavian Airlines, and Delta fly from Chicago to Wales in about 10h 15m. The time it takes to get you to your destination can typically vary by up to 22h. There are 3812 mi between Chicago and Wales. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Chicago to Wales?

    While some choose either Chicago Midway - Manchester or Chicago O'Hare Intl - Bristol, Chicago O'Hare Intl - Manchester is the most popular route from Chicago to Wales.

  • Can I find deals for flights from Chicago to Wales that include hotel bookings?

    Yes. In addition to deals on Chicago to Wales flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Wales?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Wales.

  • Can I find deals for business class flights from Chicago to Wales?

    Yes. Cheapflights offers flight deals from Chicago to Wales 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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How does Cheapflights help users find flights from Chicago to Wales?

Cheapflights makes it easy to find Chicago to Wales flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Wales?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Chicago to Wales for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Chicago to Wales with no change fees?

Yes! Cheapflights helps users easily find flights from Chicago to Wales with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Wales become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Wales from Chicago today and book when prices fit your budget.

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