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Cheap flights from Chicago to Wales from £139

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 15/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CWL
26 Feb — 5 Mar1
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 27 January 2026.

Mon 13/419:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Wed 22/413:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Deal found 25/1£376
Sun 26/419:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Sat 2/513:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Deal found 26/1£390
Sun 8/319:30
ORD
-
MAN
1 stop10h 15m
Icelandair
Thu 12/311:55
MAN
-
ORD
1 stop11h 25m
Icelandair
Deal found 27/1£393
Sun 1/321:50
ORD
-
MAN
2 stops20h 05m
Multiple Airlines
Mon 9/321:30
MAN
-
ORD
2 stops21h 55m
Multiple Airlines
Deal found 26/1£397
Sun 1/320:25
ORD
-
MAN
1 stop13h 50m
TAP AIR PORTUGAL
Sat 7/311:25
MAN
-
ORD
1 stop33h 20m
TAP AIR PORTUGAL
Deal found 25/1£398
Sat 4/419:25
ORD
-
MAN
1 stop10h 15m
Icelandair
Wed 6/513:05
MAN
-
ORD
1 stop11h 10m
Icelandair
Deal found 26/1£404
Wed 25/323:35
ORD
-
MAN
2 stops18h 40m
Multiple Airlines
Thu 2/406:00
MAN
-
ORD
2 stops17h 45m
Multiple Airlines
Deal found 25/1£415
Thu 27/819:15
ORD
-
MAN
2 stops42h 40m
Scandinavian Airlines
Sun 30/812:25
MAN
-
ORD
2 stops57h 45m
Scandinavian Airlines
Deal found 25/1£416
Sat 25/418:15
ORD
-
MAN
1 stop16h 55m
TAP AIR PORTUGAL
Sat 2/510:55
MAN
-
ORD
1 stop35h 05m
TAP AIR PORTUGAL
Deal found 25/1£418
Sun 8/320:20
ORD
-
MAN
2 stops34h 55m
Scandinavian Airlines
Thu 12/310:10
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Deal found 25/1£420
Sun 1/218:14
MDW
-
MAN
1 stop30h 16m
Virgin Atlantic
Tue 17/213:30
MAN
-
MDW
1 stop15h 03m
Virgin Atlantic
Deal found 24/1£451
Tue 10/206:00
MDW
-
MAN
1 stop22h 30m
Delta
Wed 18/213:00
MAN
-
MDW
1 stop28h 59m
Delta
Deal found 24/1£456

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 27 January 2026.

Round-trip from

£376

One-way from

£139
Icelandair
  • Icelandair
  • 13/4-22/4
  • 2 total stops
  • 21h 25m total
  • Chicago to Wales
Search Deals
Icelandair
  • Icelandair
  • 15/2
  • 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 27 January 2026.
Use the filters below to find and compare flights from Chicago to Wales that are best for you.

Fly from

Chicago

Fly to

Wales

Route

Depart

Return

Price

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Mon 9/2

18:50-17:55

1 stop17h 05m

Manchester

Wed 18/2

09:10-16:20

1 stop13h 10m

£435

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Tue 17/3

19:30-10:45

1 stop10h 15m

Manchester

Tue 24/3

11:55-18:20

1 stop11h 25m

£437

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Tue 17/3

19:30-10:45

1 stop10h 15m

Manchester

Wed 25/3

08:15-18:20

2 stops15h 05m

£446

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Tue 17/3

19:30-10:45

1 stop10h 15m

Manchester

Tue 24/3

22:40-18:20

2 stops24h 40m

£446

ChicagoManchester

MDW - MAN

MDWMAN

Chicago Midway

Sat 7/2

10:53-10:30

1 stop17h 37m

Manchester

Thu 19/2

13:30-22:31

1 stop15h 01m

£456

ChicagoManchester

MDW - MAN

MDWMAN

Chicago Midway

Wed 11/3

18:07-10:30

1 stop11h 23m

Manchester

Wed 18/3

13:30-22:31

1 stop14h 01m

£456

ChicagoManchester

MDW - MAN

MDWMAN

Chicago Midway

Tue 10/2

10:48-10:30

1 stop17h 42m

Manchester

Tue 17/2

13:30-09:54

1 stop26h 24m

£456

ChicagoManchester

MDW - MAN

MDWMAN

Chicago Midway

Tue 10/2

06:00-10:30

1 stop22h 30m

Manchester

Wed 18/2

13:00-11:59

1 stop28h 59m

£456

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Thu 16/4

21:40-23:15

1 stop19h 35m

Manchester

Sun 26/4

05:55-12:55

1 stop13h 00m

£458

ChicagoManchester

ORD - MAN

ORDMAN

Chicago O'Hare Intl

Tue 17/3

12:00-10:30

2 stops17h 30m

Manchester

Thu 26/3

13:30-23:54

1 stop15h 24m

£460

Flights are sorted by cheapest return flights first.

Deals found on 26/1

Showing 1-10 of 60 results
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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 SWISS, Icelandair, 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 7h 22m. 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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Alternative routes for Chicago to Wales

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Birmingham flights
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Midway to Leeds flights
Champaign to Heathrow flights
St. Louis to Inverness 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 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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