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Cheap flights from Chicago to Wales from £185

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 25/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CWL
25 Aug — 1 Sep1
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 26 July 2026.

Sat 24/1019:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Thu 5/1108:00
MAN
-
ORD
2 stops15h 20m
Multiple Airlines
Deal found 24/7£497
Sat 24/1019:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Mon 2/1107:45
MAN
-
ORD
2 stops15h 35m
Multiple Airlines
Deal found 24/7£499
Sat 12/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Thu 24/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Deal found 22/7£502
Tue 15/919:25
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Thu 24/906:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Deal found 22/7£503
Sat 24/1019:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Fri 6/1106:35
MAN
-
ORD
2 stops16h 45m
Multiple Airlines
Deal found 24/7£503
Sun 25/1019:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Fri 6/1106:35
MAN
-
ORD
2 stops16h 45m
Multiple Airlines
Deal found 24/7£504
Wed 14/1022:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Tue 24/1115:55
MAN
-
ORD
2 stops29h 35m
Multiple Airlines
Deal found 22/7£506
Fri 18/922:25
ORD
-
MAN
1 stop31h 15m
Multiple Airlines
Thu 1/1006:55
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Deal found 26/7£506
Wed 9/919:25
ORD
-
BRS
2 stops21h 45m
Multiple Airlines
Wed 16/911:45
BRS
-
ORD
2 stops30h 55m
Multiple Airlines
Deal found 26/7£507
Tue 8/919:25
ORD
-
MAN
2 stops21h 50m
Multiple Airlines
Tue 15/913:40
MAN
-
ORD
2 stops34h 35m
Multiple Airlines
Deal found 24/7£507
Sat 24/1019:30
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Fri 30/1006:35
MAN
-
ORD
2 stops16h 45m
Multiple Airlines
Deal found 25/7£509
Tue 8/909:55
ORD
-
MAN
2 stops25h 30m
Multiple Airlines
Tue 22/922:45
MAN
-
ORD
3 stops27h 03m
Multiple Airlines
Deal found 26/7£515

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 26 July 2026.

Round-trip from

£497

One-way from

£185
24/10-5/11
  • 24/10-5/11
  • 3 total stops
  • 25h 35m total
  • Chicago to Wales
Search Deals
Icelandair
  • Icelandair
  • 25/11
  • 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 26 July 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

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Sun 29/11

18:30-10:45

1 stop10h 15m

Manchester

Thu 3/12

11:55-17:20

1 stop11h 25m

£544

ChicagoBristol

ORD - BRS

ORDBRS

Chicago O'Hare Intl

Wed 9/9

19:25-23:10

2 stops21h 45m

Bristol

Wed 16/9

12:30-12:40

2 stops30h 10m

£554

ChicagoBristol

ORD - BRS

ORDBRS

Chicago O'Hare Intl

Mon 7/9

22:25-19:05

2 stops14h 40m

Bristol

Mon 14/9

17:35-21:20

2 stops33h 45m

£561

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Sun 13/9

19:25-11:40

1 stop10h 15m

Manchester

Tue 29/9

13:05-18:15

1 stop11h 10m

£564

ChicagoBristol

ORD - BRS

ORDBRS

Chicago O'Hare Intl

Tue 8/9

08:45-22:55

3 stops32h 10m

Bristol

Tue 15/9

18:00-21:20

2 stops33h 20m

£603

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Sun 16/8

19:25-11:40

1 stop10h 15m

Manchester

Wed 26/8

13:05-18:15

1 stop11h 10m

£620

ChicagoBristol

ORD - BRS

ORDBRS

Chicago O'Hare Intl

Mon 14/9

15:45-07:35

1 stop9h 50m

Bristol

Mon 21/9

08:20-14:25

1 stop36h 05m

£635

ChicagoCardiff

ORD - CWL

ORDCWL

Chicago O'Hare Intl

Tue 8/9

08:45-23:25

3 stops32h 40m

Cardiff Wales

Tue 15/9

11:00-19:48

3 stops38h 48m

£650

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Tue 1/12

17:58-08:40

2 stops32h 42m

Manchester

Tue 15/12

11:30-18:20

2 stops36h 50m

£653

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Wed 20/1

13:31-09:00

2 stops13h 29m

Manchester

Thu 28/1

09:45-18:45

1 stop15h 00m

£658

Flights are sorted by cheapest return flights first.

Deals found on 25/7

Showing 1-10 of 60 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, United Airlines, and British Airways 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 27m. 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 - Cardiff Wales, 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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