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Cheap flights from Wales to Chicago from £258

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
22 Jan — 29 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 23 December 2025.

Sun 28/1206:00BRS - ORD
1 stop14h 20mDelta
Tue 13/106:00ORD - BRS
2 stops22h 15mDelta
Deal found 20/12£605
Sun 28/1206:00BRS - ORD
1 stop14h 20mDelta
Mon 12/117:40ORD - BRS
2 stops34h 35mDelta
Deal found 20/12£609
Sun 28/1206:00BRS - ORD
1 stop14h 20mDelta
Wed 7/107:10ORD - BRS
2 stops21h 05mDelta
Deal found 20/12£659
Sun 28/1206:00BRS - ORD
2 stops35h 35mDelta
Sun 11/107:10ORD - BRS
2 stops21h 05mDelta
Deal found 20/12£663
Sun 28/1208:25BRS - ORD
1 stop15h 30mMultiple Airlines
Wed 7/121:00ORD - BRS
1 stop10h 25mMultiple Airlines
Deal found 22/12£686
Sun 21/1214:30MAN - ORD
2 stops49h 35mMultiple Airlines
Sat 10/118:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 20/12£719
Sun 28/1206:00BRS - ORD
2 stops35h 35mDelta
Fri 9/106:50ORD - BRS
2 stops21h 05mDelta
Deal found 20/12£725
Wed 24/1208:15MAN - ORD
1 stop11h 45mMultiple Airlines
Wed 31/1215:50ORD - MAN
1 stop16h 10mMultiple Airlines
Deal found 22/12£730
Sat 27/1207:50BRS - ORD
2 stops32h 04mMultiple Airlines
Fri 9/121:00ORD - BRS
1 stop12h 50mMultiple Airlines
Deal found 22/12£741
Sat 27/1207:50BRS - ORD
2 stops29h 37mMultiple Airlines
Sun 11/121:00ORD - BRS
1 stop15h 40mMultiple Airlines
Deal found 20/12£744
Mon 29/1205:50MAN - ORD
1 stop14h 30mVirgin Atlantic
Sun 4/117:20ORD - MAN
1 stop10h 50mVirgin Atlantic
Deal found 21/12£750
Sun 28/1208:25BRS - ORD
1 stop15h 30mMultiple Airlines
Sun 11/121:00ORD - BRS
1 stop15h 40mMultiple Airlines
Deal found 20/12£756

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 23 December 2025.

Round-trip from

£399

One-way from

£258
Scandinavian Airlines
  • Scandinavian Airlines
  • 5/2-12/2
  • 4 total stops
  • 51h 45m total
  • Wales to Chicago
Search Deals
3/3
  • 3/3
  • 2 total stops
  • 33h 02m 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 23 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

Wed 4/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 11/2

19:20-12:15

2 stops34h 55m

£404

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 9/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 15/2

19:10-18:35

1 stop17h 25m

£406

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/2

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 9/2

19:20-09:30

1 stop32h 10m

£412

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

20:55-16:45

2 stops25h 50m

Chicago O'Hare Intl

Sun 15/2

19:10-20:05

2 stops18h 55m

£423

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 8/4

21:10-16:10

2 stops49h 00m

Chicago O'Hare Intl

Wed 22/4

19:15-20:30

2 stops19h 15m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 15/4

21:10-16:10

2 stops49h 00m

Chicago O'Hare Intl

Wed 22/4

19:15-20:30

2 stops19h 15m

£436

BristolChicago

BRS - ORD

BRSORD

Bristol

Thu 5/2

13:50-16:45

2 stops32h 55m

Chicago O'Hare Intl

Thu 12/2

19:20-21:40

2 stops20h 20m

£453

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 13/2

13:25-22:31

1 stop15h 06m

Chicago Midway

Wed 18/2

12:45-08:45

1 stop14h 00m

£457

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 3/2

09:00-19:15

1 stop16h 15m

Chicago O'Hare Intl

Tue 10/2

21:00-18:40

1 stop15h 40m

£471

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 17/1

12:55-16:55

2 stops34h 00m

Chicago O'Hare Intl

Fri 30/1

19:10-16:45

2 stops39h 35m

£472

Flights are sorted by cheapest return flights first.

Deals found on 22/12

Showing 1-10 of 55 results
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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?

    Scandinavian Airlines, Virgin Atlantic, and Delta can get you from Wales to Chicago in just under 14h 57m. Your travel time can differ by up to 12h 33m. 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

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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.
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Southampton to O'Hare Intl flights
Belfast Intl to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Gatwick to Champaign flights
Heathrow to Champaign flights
Leeds to O'Hare Intl flights
Norwich to O'Hare Intl flights
Belfast City to O'Hare Intl flights
Newquay to O'Hare Intl flights
Heathrow to Peoria flights
Liverpool to O'Hare Intl flights
London City to Midway flights
Edinburgh to Moline flights
Leeds to Midway flights
Inverness to O'Hare Intl flights
Southampton to Midway flights
Cardiff to O'Hare Intl flights
Southend to O'Hare Intl flights
Heathrow to Moline flights
Grimsby to St. Louis flights
Newcastle upon Tyne to St. Louis flights

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How does Cheapflights help users find flights from Wales to Chicago?

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