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Cheap flights from Wales to Chicago from £252

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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
15 Oct — 22 Oct1
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 15 September 2025.

Round-trip from

£386

One-way from

£252
29/10-5/11
  • 29/10-5/11
  • 4 total stops
  • 40h 05m total
  • Wales to Chicago
Search Deals
6/11
  • 6/11
  • 2 total stops
  • 28h 55m total
  • Wales to Chicago
Search Deals

Find flight deals from Wales to Chicago

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 15 September 2025.

Wed 29/1007:15BRS - ORD
2 stops18h 50mMultiple Airlines
Wed 5/1119:20ORD - BRS
2 stops21h 15mMultiple Airlines
Deal found 14/9£386
Tue 2/1219:15MAN - ORD
1 stop27h 30mScandinavian Airlines
Tue 9/1210:31ORD - MAN
2 stops26h 04mScandinavian Airlines
Deal found 14/9£444
Tue 18/1117:15MAN - ORD
1 stop27h 45mTAP AIR PORTUGAL
Wed 3/1219:10ORD - MAN
1 stop15h 05mTAP AIR PORTUGAL
Deal found 14/9£446
Wed 24/912:15MAN - ORD
1 stop12h 00mIcelandair
Wed 1/1019:25ORD - MAN
1 stop9h 50mIcelandair
Deal found 14/9£447
Thu 6/1116:20MAN - ORD
2 stops28h 55mMultiple Airlines
Thu 13/1105:05ORD - MAN
3 stops23h 30mMultiple Airlines
Deal found 12/9£448
Tue 23/1212:55MAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 31/1219:20ORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 15/9£450
Fri 26/1220:55MAN - ORD
2 stops49h 50mScandinavian Airlines
Wed 21/119:20ORD - MAN
2 stops58h 55mScandinavian Airlines
Deal found 12/9£450
Wed 17/1210:10MAN - ORD
1 stop12h 35mScandinavian Airlines
Fri 26/1219:20ORD - MAN
1 stop32h 10mScandinavian Airlines
Deal found 14/9£453
Wed 24/912:15MAN - ORD
1 stop15h 00mIcelandair
Tue 30/919:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 14/9£453
Wed 15/1013:40MAN - ORD
2 stops28h 55mMultiple Airlines
Wed 5/1119:10ORD - MAN
2 stops20h 05mMultiple Airlines
Deal found 14/9£454
Wed 24/912:15MAN - ORD
1 stop15h 00mIcelandair
Wed 8/1019:25ORD - MAN
1 stop10h 15mIcelandair
Deal found 14/9£455
Fri 7/1113:25MAN - MDW
1 stop14h 49mVirgin Atlantic
Wed 12/1113:14MDW - MAN
2 stops14h 56mVirgin Atlantic
Deal found 13/9£495

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 15 September 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

BristolChicago

BRS - ORD

BRSORD

Bristol

Wed 29/10

07:15-21:05

2 stops18h 50m

Chicago O'Hare Intl

Wed 5/11

19:20-22:35

2 stops21h 15m

£386

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 23/12

12:55-16:45

2 stops33h 50m

Chicago O'Hare Intl

Wed 31/12

19:20-12:15

2 stops34h 55m

£450

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 26/12

20:55-16:45

2 stops49h 50m

Chicago O'Hare Intl

Wed 21/1

19:20-12:15

2 stops58h 55m

£450

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sat 14/2

19:20-18:35

1 stop17h 15m

£453

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 21/11

11:55-17:20

1 stop11h 25m

Chicago O'Hare Intl

Tue 9/12

18:30-10:45

1 stop10h 15m

£467

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 22/11

11:55-17:20

1 stop11h 25m

Chicago O'Hare Intl

Tue 9/12

18:30-10:45

1 stop10h 15m

£467

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 15/10

12:40-18:15

1 stop11h 35m

Chicago O'Hare Intl

Wed 22/10

19:25-11:15

1 stop9h 50m

£469

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/2

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Sun 15/2

19:10-18:35

1 stop17h 25m

£469

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 25/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Thu 1/1

19:20-09:30

1 stop32h 10m

£469

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 17/12

10:10-16:45

1 stop12h 35m

Chicago O'Hare Intl

Fri 26/12

19:20-08:40

2 stops31h 20m

£474

Flights are sorted by cheapest return flights first.

Deals found on 14/9

Showing 1-10 of 45 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, Icelandair, and Delta can get you from Wales to Chicago in just under 11h 25m. Your travel time can differ by up to 22h 25m. 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 Cardiff Wales - 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.

  • What is the cheapest month to book a flight from Wales to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Wales to Chicago (average of £595). Flying from Wales to Chicago in July is currently the most expensive (average of £843). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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