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Cheap flights from Wales to Chicago from £282

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 16/12. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Wales to Chicago

Keep the following information in mind while searching for Wales to Chicago flight deals. Data was last updated 4 November 2025.

Round-trip from

£425

One-way from

£282
Scandinavian Airlines
  • Scandinavian Airlines
  • 21/11-3/12
  • 2 total stops
  • 44h 45m total
  • Wales to Chicago
Search Deals
16/12
  • 16/12
  • 2 total stops
  • 38h 40m total
  • Wales to Chicago
Search Deals

Find 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 4 November 2025.

Fri 21/1119:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Wed 3/1219:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 3/11£425
Mon 1/1212:55MAN - ORD
2 stops57h 50mScandinavian Airlines
Sat 6/1219:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 2/11£426
Tue 2/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Mon 8/1219:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 2/11£430
Sat 15/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sun 23/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 1/11£431
Tue 11/1112:55MAN - ORD
2 stops57h 50mScandinavian Airlines
Wed 19/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 2/11£433
Wed 12/1119:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Thu 11/1219:20ORD - MAN
1 stop32h 10mScandinavian Airlines
Deal found 1/11£435
Sun 23/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sun 30/1119:20ORD - MAN
2 stops40h 35mScandinavian Airlines
Deal found 1/11£440
Wed 12/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Wed 10/1219:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 1/11£447
Tue 2/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Fri 5/1219:20ORD - MAN
2 stops31h 20mScandinavian Airlines
Deal found 2/11£457
Wed 12/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 19/1119:20ORD - MAN
2 stops55h 15mScandinavian Airlines
Deal found 2/11£458
Tue 23/1214:00BRS - ORD
3 stops32h 45mMultiple Airlines
Wed 31/1219:20ORD - BRS
2 stops20h 25mMultiple Airlines
Deal found 4/11£541
Fri 19/1208:00BRS - ORD
1 stop12h 00mMultiple Airlines
Fri 26/1219:40ORD - BRS
1 stop18h 00mMultiple Airlines
Deal found 4/11£555

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 4 November 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 21/11

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 3/12

19:20-18:35

1 stop17h 15m

£425

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 2/12

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 8/12

19:20-18:35

1 stop17h 15m

£430

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 15/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 23/11

19:20-18:35

1 stop17h 15m

£431

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 1/12

12:55-16:45

2 stops57h 50m

Chicago O'Hare Intl

Mon 8/12

19:20-18:35

1 stop17h 15m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 13/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Wed 19/11

19:20-08:35

2 stops55h 15m

£468

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 1/12

12:55-16:45

2 stops57h 50m

Chicago O'Hare Intl

Thu 4/12

19:20-18:35

1 stop17h 15m

£478

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 1/12

12:55-16:45

2 stops57h 50m

Chicago O'Hare Intl

Fri 5/12

19:20-09:30

1 stop32h 10m

£478

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 14/11

11:55-17:20

1 stop11h 25m

Chicago O'Hare Intl

Tue 25/11

18:30-10:45

1 stop10h 15m

£480

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 13/11

11:55-17:20

1 stop11h 25m

Chicago O'Hare Intl

Tue 18/11

18:30-10:45

1 stop10h 15m

£494

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 3/12

13:05-17:20

3 stops34h 15m

Chicago O'Hare Intl

Mon 8/12

18:30-12:15

3 stops35h 45m

£499

Flights are sorted by cheapest return flights first.

Deals found on 3/11

Showing 1-10 of 44 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 27h 30m. Your travel time can differ by up to 5h 34m. The distance from Wales to Chicago is about 3812 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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