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$346+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
Apr 19 — Apr 261
Sun 4/19
Sun 4/26
1 adult, Economy
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Cheap 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 March 20, 2026.

This Trip.com deal was found by Cheapflights users on 3/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2210:10 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 11/297:20 pm
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 3/20$610
This The Travel House deal was found by Cheapflights users on 3/18. 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 5/19:35 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 5/317:15 pm
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 3/18$614
This The Travel House deal was found by Cheapflights users on 3/18. 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 5/19:35 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Mon 6/17:15 pm
ORD
-
MAN
2 stops34h 50m
Scandinavian Airlines
Deal found 3/18$618
This Trip.com deal was found by Cheapflights users on 3/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:35 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Thu 5/287:15 pm
ORD
-
MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 3/19$623
This The Travel House deal was found by Cheapflights users on 3/19. 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.
Tue 5/197:10 pm
MAN
-
ORD
1 stop27h 00m
Scandinavian Airlines
Tue 6/27:15 pm
ORD
-
MAN
2 stops32h 25m
Scandinavian Airlines
Deal found 3/19$624
This The Travel House deal was found by Cheapflights users on 3/19. 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 10/98:25 pm
MAN
-
ORD
2 stops49h 45m
Scandinavian Airlines
Wed 10/147:15 pm
ORD
-
MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 3/19$625
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 4/136:50 pm
MAN
-
ORD
2 stops29h 25m
Multiple Airlines
Mon 4/207:25 pm
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 3/16$628
This Mytrip deal was found by Cheapflights users on 3/16. 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 4/308:55 am
BRS
-
ORD
1 stop16h 20m
Multiple Airlines
Thu 5/79:00 pm
ORD
-
BRS
1 stop19h 55m
Multiple Airlines
Deal found 3/16$719
This Booking.com deal was found by Cheapflights users on 3/16. 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.
Mon 4/208:20 am
BRS
-
ORD
3 stops46h 04m
Multiple Airlines
Fri 4/247:25 pm
ORD
-
BRS
2 stops15h 20m
Multiple Airlines
Deal found 3/16$752
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Sat 5/27:45 am
BRS
-
ORD
1 stop17h 30m
Multiple Airlines
Sat 5/93:45 pm
ORD
-
BRS
1 stop11h 45m
Multiple Airlines
Deal found 3/18$767
This Booking.com deal was found by Cheapflights users on 3/17. 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.
Tue 4/1412:40 pm
BRS
-
ORD
2 stops31h 50m
Multiple Airlines
Tue 4/215:10 pm
ORD
-
BRS
2 stops21h 20m
Multiple Airlines
Deal found 3/17$772
This Booking.com deal was found by Cheapflights users on 3/17. 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.
Tue 4/2812:40 pm
BRS
-
ORD
2 stops31h 50m
Multiple Airlines
Tue 5/55:10 pm
ORD
-
BRS
2 stops21h 20m
Multiple Airlines
Deal found 3/17$776

Find flight deals from Wales to Chicago

Keep the following information in mind while searching for Wales to Chicago flight deals. Data was last updated March 20, 2026.

Round-trip from

$614
(The Travel House)

One-way from

$346
(Kiwi.com)
From Wales to Chicago (CHI)
Search Deals
One-way flight from Wales to Chicago (CHI)
Search Deals

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 March 20, 2026.
Use the filters below to find and compare flights from Wales to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 4/20

8:20 am-12:24 am

3 stops46h 04m

Chicago O'Hare Intl

Fri 4/24

7:25 pm-4:45 pm

2 stops15h 20m

$752

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 5/4

8:20 am-2:15 pm

2 stops35h 55m

Chicago O'Hare Intl

Mon 5/11

5:10 pm-11:15 pm

2 stops24h 05m

$804

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 6/5

7:10 pm-4:10 pm

1 stop27h 00m

Chicago O'Hare Intl

Thu 6/18

7:15 pm-6:30 pm

1 stop17h 15m

$874

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 4/29

10:35 am-6:15 pm

1 stop13h 40m

Chicago O'Hare Intl

Wed 5/6

10:30 pm-5:35 pm

1 stop13h 05m

$883

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Wed 4/29

9:45 am-2:30 pm

1 stop10h 45m

Chicago O'Hare Intl

Wed 5/6

12:14 pm-9:15 am

2 stops15h 01m

$888

BristolChicago

BRS - ORD

BRSORD

Bristol

Wed 4/29

9:20 am-2:30 pm

1 stop11h 10m

Chicago O'Hare Intl

Wed 5/6

10:15 am-8:50 am

2 stops16h 35m

$894

CardiffChicago

CWL - ORD

CWLORD

Cardiff Wales

Mon 5/4

5:15 pm-2:15 pm

1 stop27h 00m

Chicago O'Hare Intl

Mon 5/11

4:50 pm-4:45 pm

1 stop17h 55m

$894

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 4/17

8:25 pm-4:10 pm

2 stops25h 45m

Chicago O'Hare Intl

Sun 4/19

6:04 am-7:45 pm

2 stops31h 41m

$896

CardiffChicago

CWL - MDW

CWLMDW

Cardiff Wales

Wed 4/29

9:45 am-10:28 pm

2 stops18h 43m

Chicago Midway

Wed 5/6

9:29 am-9:15 am

2 stops17h 46m

$898

BristolChicago

BRS - MDW

BRSMDW

Bristol

Tue 4/28

6:15 am-6:36 pm

2 stops18h 21m

Chicago Midway

Tue 5/5

9:29 am-8:50 am

2 stops17h 21m

$903

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 53 resultsSorted by cheapest first
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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 10h 45m. Scandinavian Airlines provides one of the quickest options available for as low as $888. The distance from Wales to Chicago is about 3831 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 Bristol - Chicago O'Hare Intl.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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