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$342+ Cheap flights from Wales to Chicago (CHI)

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$525
(Mytrip)

One-way from

$342
(Mytrip)
From Wales to Chicago (CHI)
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One-way flight from Wales to Chicago (CHI)
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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 September 15, 2025.

This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:15 amBRS - ORD
2 stops18h 50mMultiple Airlines
Wed 11/57:20 pmORD - BRS
2 stops21h 15mMultiple Airlines
Deal found 9/14$525
This lastminute.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:15 pmMAN - ORD
1 stop27h 30mScandinavian Airlines
Tue 12/910:31 amORD - MAN
2 stops26h 04mScandinavian Airlines
Deal found 9/14$603
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/185:15 pmMAN - ORD
1 stop27h 45mTAP AIR PORTUGAL
Wed 12/37:10 pmORD - MAN
1 stop15h 05mTAP AIR PORTUGAL
Deal found 9/14$606
This Gotogate deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:15 pmMAN - ORD
1 stop12h 00mIcelandair
Wed 10/17:25 pmORD - MAN
1 stop9h 50mIcelandair
Deal found 9/14$608
This Mytrip deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:20 pmMAN - ORD
2 stops28h 55mMultiple Airlines
Thu 11/135:05 amORD - MAN
3 stops23h 30mMultiple Airlines
Deal found 9/12$609
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:55 pmMAN - ORD
2 stops33h 50mScandinavian Airlines
Wed 12/317:20 pmORD - MAN
2 stops34h 55mScandinavian Airlines
Deal found 9/15$611
This The Travel House deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure The Travel House is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/268:55 pmMAN - ORD
2 stops49h 50mScandinavian Airlines
Wed 1/217:20 pmORD - MAN
2 stops58h 55mScandinavian Airlines
Deal found 9/12$612
This FlightHub deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:10 amMAN - ORD
1 stop12h 35mScandinavian Airlines
Fri 12/267:20 pmORD - MAN
1 stop32h 10mScandinavian Airlines
Deal found 9/14$615
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:15 pmMAN - ORD
1 stop15h 00mIcelandair
Tue 9/307:25 pmORD - MAN
1 stop10h 15mIcelandair
Deal found 9/14$616
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/151:40 pmMAN - ORD
2 stops28h 55mMultiple Airlines
Wed 11/57:10 pmORD - MAN
2 stops20h 05mMultiple Airlines
Deal found 9/14$617
This oojo deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:15 pmMAN - ORD
1 stop15h 00mIcelandair
Wed 10/87:25 pmORD - MAN
1 stop10h 15mIcelandair
Deal found 9/14$618
This Netflights deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Netflights is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:25 pmMAN - MDW
1 stop14h 49mVirgin Atlantic
Wed 11/121:14 pmMDW - MAN
2 stops14h 56mVirgin Atlantic
Deal found 9/13$673

Cheapflights Fare Finder

 
Customize 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 2,558,603 searches. Data last updated September 15, 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 10/29

7:15 am-9:05 pm

2 stops18h 50m

Chicago O'Hare Intl

Wed 11/5

7:20 pm-10:35 pm

2 stops21h 15m

$525

ManchesterChicago

MAN - ORD

MANORD

Manchester

Tue 12/23

12:55 pm-4:45 pm

2 stops33h 50m

Chicago O'Hare Intl

Wed 12/31

7:20 pm-12:15 pm

2 stops34h 55m

$611

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 11/6

12:55 pm-4:45 pm

2 stops33h 50m

Chicago O'Hare Intl

Wed 1/7

7:20 pm-12:15 pm

2 stops34h 55m

$633

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 11/21

11:55 am-5:20 pm

1 stop11h 25m

Chicago O'Hare Intl

Tue 12/9

6:30 pm-10:45 am

1 stop10h 15m

$634

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 11/22

11:55 am-5:20 pm

1 stop11h 25m

Chicago O'Hare Intl

Tue 12/9

6:30 pm-10:45 am

1 stop10h 15m

$634

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 2/6

10:10 am-4:45 pm

1 stop12h 35m

Chicago O'Hare Intl

Sun 2/15

7:10 pm-6:35 pm

1 stop17h 25m

$637

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 2/7

10:10 am-4:45 pm

1 stop12h 35m

Chicago O'Hare Intl

Sun 2/15

7:10 pm-6:35 pm

1 stop17h 25m

$637

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 12/17

10:10 am-4:45 pm

1 stop12h 35m

Chicago O'Hare Intl

Fri 12/26

7:20 pm-8:40 am

2 stops31h 20m

$644

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 10/1

12:40 pm-6:15 pm

1 stop11h 35m

Chicago O'Hare Intl

Sun 10/5

7:25 pm-11:40 am

1 stop10h 15m

$645

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 10/25

7:10 pm-5:55 pm

1 stop28h 45m

Chicago O'Hare Intl

Sun 11/2

7:20 pm-6:35 pm

1 stop17h 15m

$669

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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 round-trip 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?

    A quick flight from Wales to Chicago can take about 11h 25m. Scandinavian Airlines provides one of the quickest options available for as low as $634. The distance from Wales to Chicago is about 3812 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Wales to Chicago?

    The most popular route from Wales to Chicago is Manchester - Chicago O'Hare Intl. You may also consider Manchester - Chicago Midway or Cardiff Wales - Chicago Midway.

  • 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 vacation 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, August is the cheapest month in which you can book a flight from Wales to Chicago (average of $245). Flying from Wales to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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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