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Cheap flights from Wales to Chicago from £224

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 22/11. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
16 Nov — 23 Nov1
1 adult
1 adult, Economy

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 17 October 2025.

Round-trip from

£416

One-way from

£224
22/11-29/11
  • 22/11-29/11
  • 2 total stops
  • 25h 20m total
  • Wales to Chicago
Search Deals
22/11
  • 22/11
  • 2 total stops
  • 28h 15m 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 17 October 2025.

Sat 22/1108:45MAN - ORD
1 stop15h 10mMultiple Airlines
Sat 29/1115:50ORD - MAN
1 stop10h 10mMultiple Airlines
Deal found 16/10£416
Sat 1/1110:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Sat 15/1119:20ORD - MAN
2 stops18h 25mScandinavian Airlines
Deal found 16/10£417
Sat 22/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Sat 29/1119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 16/10£418
Sun 23/1109:20MAN - ORD
2 stops37h 25mScandinavian Airlines
Sun 30/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 16/10£425
Tue 16/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Mon 12/119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 15/10£430
Wed 12/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 19/1119:20ORD - MAN
1 stop17h 15mScandinavian Airlines
Deal found 15/10£433
Tue 4/1112:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Sun 9/1119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/10£434
Sun 16/1108:25BRS - ORD
1 stop11h 35mMultiple Airlines
Sun 23/1115:50ORD - BRS
1 stop9h 45mMultiple Airlines
Deal found 17/10£444
Mon 15/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Thu 15/119:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/10£466
Mon 1/1208:00BRS - ORD
1 stop12h 00mMultiple Airlines
Mon 8/1215:50ORD - BRS
1 stop10h 15mMultiple Airlines
Deal found 17/10£475
Mon 3/1108:00BRS - ORD
1 stop14h 00mMultiple Airlines
Fri 7/1119:40ORD - BRS
1 stop14h 10mMultiple Airlines
Deal found 16/10£504
Tue 4/1108:20BRS - ORD
1 stop11h 40mAer Lingus
Sat 8/1115:50ORD - BRS
1 stop10h 20mAer Lingus
Deal found 15/10£532

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 17 October 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

Sat 22/11

08:45-17:55

1 stop15h 10m

Chicago O'Hare Intl

Sat 29/11

15:50-08:00

1 stop10h 10m

£416

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/3

19:15-16:55

1 stop27h 40m

Chicago O'Hare Intl

Mon 9/3

20:20-17:55

2 stops16h 35m

£416

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 1/11

10:10-17:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 15/11

19:20-19:45

2 stops18h 25m

£417

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 22/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 29/11

19:20-12:15

2 stops34h 55m

£420

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 16/12

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Mon 12/1

19:20-18:35

1 stop17h 15m

£430

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 7/1

19:15-16:45

1 stop27h 30m

Chicago O'Hare Intl

Wed 4/3

19:20-18:35

1 stop17h 15m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 12/11

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Wed 19/11

19:20-18:35

1 stop17h 15m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 5/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 13/2

19:20-08:40

2 stops31h 20m

£433

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 17/11

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 21/11

19:20-08:40

2 stops31h 20m

£469

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 1/12

08:00-14:00

1 stop12h 00m

Chicago O'Hare Intl

Mon 8/12

15:50-08:05

1 stop10h 15m

£475

Flights are sorted by cheapest return flights first.

Deals found on 16/10

Showing 1-10 of 51 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, Aer Lingus, and Virgin Atlantic can get you from Wales to Chicago in just under 11h 40m. Your travel time can differ by up to 16h. The distance from Wales to Chicago is about 3855 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 O'Hare Intl, 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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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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