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Cheap flights from Wales to Chicago from £220

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
25 Dec — 1 Jan1
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 25 November 2025.

Round-trip from

£428

One-way from

£220
7/2-15/2
  • 7/2-15/2
  • 4 total stops
  • 38h 05m total
  • Wales to Chicago
Search Deals
3/3
  • 3/3
  • 3 total stops
  • 41h 08m 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 25 November 2025.

Wed 3/1212:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Mon 8/1219:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 23/11£436
Sat 6/1221:20MAN - ORD
2 stops23h 25mMultiple Airlines
Tue 9/1218:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 23/11£456
Wed 24/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Wed 7/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 24/11£463
Mon 15/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sun 18/119:10ORD - MAN
1 stop17h 25mScandinavian Airlines
Deal found 24/11£472
Thu 25/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Wed 7/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 24/11£476
Wed 24/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Wed 31/1219:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 24/11£498
Sun 14/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Wed 7/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 23/11£504
Sun 14/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sat 10/119:20ORD - MAN
2 stops18h 25mScandinavian Airlines
Deal found 23/11£508
Thu 25/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sun 4/119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 24/11£516
Sun 14/1208:00MAN - ORD
2 stops36h 57mMultiple Airlines
Wed 7/118:30ORD - MAN
1 stop10h 15mMultiple Airlines
Deal found 24/11£526
Wed 3/1208:20BRS - ORD
1 stop11h 40mAer Lingus
Tue 23/1215:50ORD - BRS
1 stop9h 50mAer Lingus
Deal found 23/11£645
Tue 23/1208:20BRS - ORD
1 stop11h 40mAer Lingus
Sat 10/121:00ORD - BRS
1 stop15h 40mAer Lingus
Deal found 21/11£692

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 25 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

Thu 25/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Wed 7/1

19:20-18:35

1 stop17h 15m

£476

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 14/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Wed 7/1

19:20-18:35

1 stop17h 15m

£504

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 14/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 9/1

19:20-08:40

2 stops31h 20m

£508

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 24/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 5/1

19:20-18:35

1 stop17h 15m

£511

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 15/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Thu 8/1

19:20-09:30

1 stop32h 10m

£539

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 14/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Mon 5/1

19:20-18:35

1 stop17h 15m

£539

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 15/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 10/1

19:20-20:05

2 stops42h 45m

£543

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 15/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Wed 7/1

19:20-08:35

2 stops31h 15m

£546

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 14/12

20:30-16:45

2 stops26h 15m

Chicago O'Hare Intl

Sat 10/1

19:20-19:45

2 stops18h 25m

£546

BristolChicago

BRS - ORD

BRSORD

Bristol

Sun 11/1

15:00-19:15

1 stop34h 15m

Chicago O'Hare Intl

Sat 17/1

12:00-20:50

2 stops26h 50m

£589

Flights are sorted by cheapest return flights first.

Deals found on 23/11

Showing 1-10 of 50 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 12h 35m. Your travel time can differ by up to 2h 17m. 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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London City to Peoria flights
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How does Cheapflights help users find flights from Wales to Chicago?

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Why should you use Cheapflights to find cheap flight tickets from Wales to Chicago?

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Users can book flights with no change fees policies with our dedicated filters. Book flights from Wales to Chicago flexibly with Cheapflights today.

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