Find flights
When to book
FAQs

Cheap flights from Wales to Chicago from £304

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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
15 Jan — 22 Jan1
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 16 December 2025.

Wed 24/1208:15MAN - ORD
1 stop11h 45mMultiple Airlines
Sat 27/1219:40ORD - MAN
1 stop19h 40mMultiple Airlines
Deal found 13/12£575
Mon 29/1218:20MAN - ORD
1 stop26h 35mBritish Airways
Thu 8/120:45ORD - MAN
1 stop11h 35mBritish Airways
Deal found 13/12£695
Thu 18/1215:30MAN - ORD
2 stops34h 30mMultiple Airlines
Wed 31/1218:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 15/12£701
Wed 31/1210:25MAN - ORD
2 stops29h 11mDelta
Thu 8/113:55ORD - MAN
2 stops14h 15mDelta
Deal found 13/12£703
Wed 31/1210:25MAN - MDW
2 stops28h 40mDelta
Thu 8/109:32MDW - MAN
2 stops18h 38mDelta
Deal found 13/12£707
Tue 30/1206:10MAN - ORD
2 stops42h 15mMultiple Airlines
Thu 8/118:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 13/12£715
Wed 31/1210:25MAN - MDW
2 stops28h 40mDelta
Wed 7/117:31MDW - MAN
1 stop10h 59mDelta
Deal found 13/12£725
Wed 31/1210:30MAN - ORD
2 stops17h 54mMultiple Airlines
Fri 9/118:30ORD - MAN
1 stop10h 30mMultiple Airlines
Deal found 13/12£725
Mon 29/1218:20MAN - ORD
1 stop26h 35mBritish Airways
Fri 9/114:14ORD - MAN
2 stops15h 41mBritish Airways
Deal found 13/12£726
Wed 31/1210:30MAN - ORD
1 stop14h 32mMultiple Airlines
Wed 7/118:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 13/12£727
Mon 15/1216:25MAN - ORD
2 stops32h 00mMultiple Airlines
Sat 31/118:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 15/12£728
Mon 29/1205:50MAN - ORD
1 stop14h 30mDelta
Wed 7/117:20ORD - MAN
1 stop10h 50mDelta
Deal found 13/12£737

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 16 December 2025.

Round-trip from

£402

One-way from

£304
Scandinavian Airlines
  • Scandinavian Airlines
  • 1/2-28/2
  • 3 total stops
  • 47h 40m total
  • Wales to Chicago
Search Deals
8/4
  • 8/4
  • 2 total stops
  • 16h 20m 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 16 December 2025.
Use the filters below to find and compare flights from Wales to Chicago that are best for you.

Fly from

Wales

Fly to

Chicago

Route

Depart

Return

Price

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

Sun 8/2

19:10-20:05

2 stops18h 55m

£409

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 31/1

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Wed 4/2

19:20-18:35

1 stop17h 15m

£413

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 13/3

10:10-17:55

1 stop12h 45m

Chicago O'Hare Intl

Wed 1/4

19:35-08:55

1 stop31h 20m

£428

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 10/3

19:15-17:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 1/4

19:35-08:55

1 stop31h 20m

£428

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 11/3

19:15-17:45

1 stop27h 30m

Chicago O'Hare Intl

Fri 3/4

19:15-11:45

2 stops34h 30m

£431

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 8/3

19:15-17:45

1 stop27h 30m

Chicago O'Hare Intl

Fri 3/4

19:15-11:45

2 stops34h 30m

£431

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 9/3

20:45-17:45

2 stops50h 00m

Chicago O'Hare Intl

Wed 1/4

19:35-08:55

1 stop31h 20m

£431

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 14/3

12:55-17:45

2 stops57h 50m

Chicago O'Hare Intl

Fri 3/4

19:15-11:45

2 stops34h 30m

£434

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Thu 29/1

10:30-19:15

1 stop14h 45m

Chicago O'Hare Intl

Thu 5/2

21:00-22:00

1 stop19h 00m

£509

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 25/2

13:00-22:42

1 stop15h 42m

Chicago Midway

Tue 3/3

13:28-10:10

2 stops14h 42m

£591

Flights are sorted by cheapest return flights first.

Deals found on 14/12

Showing 1-10 of 44 results
1
2
3
...
5

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, Virgin Atlantic, and Delta can get you from Wales to Chicago in just under 15h 42m. Your travel time can differ by up to 10h 08m. The distance from Wales to Chicago is about 3816 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 Midway, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Heathrow to Midway flights
London City to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Gatwick to Midway flights
Heathrow to St. Louis flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to Midway flights
Birmingham to O'Hare Intl flights
Glasgow Intl to O'Hare Intl flights
London City to St. Louis flights
Gatwick to St. Louis flights
Glasgow Intl to Midway flights
Southend to O'Hare Intl flights
Leeds to O'Hare Intl flights
Newcastle upon Tyne to O'Hare Intl flights
Southampton to O'Hare Intl flights
Birmingham to Midway flights
Heathrow to Champaign flights
Manchester to Moline flights
Edinburgh to St. Louis flights
Leeds to Midway flights
Newcastle upon Tyne to Midway flights
Manchester to St. Louis flights
Gatwick to Champaign flights
Heathrow to Springfield flights
Inverness to O'Hare Intl flights
Heathrow to Peoria flights
Norwich to O'Hare Intl flights
London City to Midway flights
Belfast Intl to O'Hare Intl flights
Heathrow to Moline flights
Exeter to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Liverpool to O'Hare Intl flights
Newcastle upon Tyne to St. Louis flights
Glasgow Intl to St. Louis flights
Newquay to O'Hare Intl flights
Bristol to Midway flights
Stansted to St. Louis flights
Bristol to O'Hare Intl flights
Darlington to O'Hare Intl flights
Cardiff to O'Hare Intl flights
Edinburgh to Moline flights
Manchester to Peoria flights
Grimsby to O'Hare Intl 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.