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$369+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
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 May 7, 2026.

This Mytrip deal was found by Cheapflights users on 5/3. 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.
Fri 6/52:40 pm
MAN
-
ORD
2 stops33h 35m
Multiple Airlines
Sun 6/147:25 pm
ORD
-
MAN
2 stops18h 20m
Multiple Airlines
Deal found 5/3$709
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Fri 11/136:55 am
MAN
-
ORD
2 stops16h 25m
Multiple Airlines
Sun 11/156:30 pm
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 5/5$712
This The Travel House deal was found by Cheapflights users on 5/4. 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.
Sat 11/2110:10 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sat 11/287:20 pm
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 5/4$729
This The Travel House deal was found by Cheapflights users on 5/5. 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 11/137:15 pm
MAN
-
ORD
1 stop27h 30m
Scandinavian Airlines
Sun 11/157:20 pm
ORD
-
MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 5/5$734
This Ticket deal was found by Cheapflights users on 5/7. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:35 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 10/258:15 pm
ORD
-
MAN
1 stop17h 20m
Scandinavian Airlines
Deal found 5/7$737
This The Travel House deal was found by Cheapflights users on 5/5. 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 11/2010:10 am
MAN
-
ORD
1 stop12h 35m
Scandinavian Airlines
Sun 11/227:20 pm
ORD
-
MAN
2 stops34h 55m
Scandinavian Airlines
Deal found 5/5$738
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Thu 9/36:55 am
MAN
-
ORD
2 stops16h 55m
Multiple Airlines
Thu 9/247:25 pm
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 5/6$743
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/91:35 pm
MAN
-
ORD
2 stops32h 25m
Multiple Airlines
Sun 8/97:25 pm
ORD
-
MAN
1 stop10h 15m
Multiple Airlines
Deal found 5/3$756
This Mytrip deal was found by Cheapflights users on 5/6. 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.
Mon 6/88:55 am
BRS
-
ORD
1 stop16h 20m
Multiple Airlines
Mon 6/159:00 pm
ORD
-
BRS
1 stop11h 05m
Multiple Airlines
Deal found 5/6$778
This Mytrip deal was found by Cheapflights users on 5/5. 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 6/108:25 am
BRS
-
ORD
1 stop11h 35m
Multiple Airlines
Tue 6/169:00 pm
ORD
-
BRS
1 stop13h 35m
Multiple Airlines
Deal found 5/5$849
This Mytrip deal was found by Cheapflights users on 5/4. 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 6/311:45 am
BRS
-
ORD
2 stops32h 30m
Multiple Airlines
Mon 6/84:50 pm
ORD
-
BRS
2 stops24h 25m
Multiple Airlines
Deal found 5/4$879
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Thu 6/47:30 pm
MAN
-
MDW
2 stops44h 05m
Multiple Airlines
Thu 6/113:20 pm
MDW
-
MAN
1 stop14h 20m
Multiple Airlines
Deal found 5/7$907

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 May 7, 2026.

Round-trip from

$709
(Mytrip)

One-way from

$369
(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 May 7, 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 6/8

5:25 pm-6:15 pm

2 stops30h 50m

Chicago O'Hare Intl

Mon 6/15

10:25 pm-8:50 am

3 stops28h 25m

$832

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 9/28

3:15 pm-7:15 pm

2 stops34h 00m

Chicago O'Hare Intl

Fri 10/16

4:55 pm-1:45 pm

1 stop14h 50m

$913

BristolChicago

BRS - ORD

BRSORD

Bristol

Tue 6/2

8:25 pm-10:05 pm

3 stops31h 40m

Chicago O'Hare Intl

Fri 6/5

9:55 am-10:05 pm

2 stops30h 10m

$916

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 9/28

5:30 pm-2:15 pm

1 stop26h 45m

Chicago O'Hare Intl

Fri 10/16

4:20 pm-10:05 pm

1 stop23h 45m

$947

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 9/28

6:15 am-5:41 pm

2 stops17h 26m

Chicago O'Hare Intl

Fri 10/16

5:20 pm-5:05 pm

2 stops17h 45m

$984

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Wed 9/16

5:55 am-6:31 pm

2 stops18h 36m

Chicago Midway

Wed 9/23

1:05 pm-7:15 am

1 stop12h 10m

$988

BristolChicago

BRS - ORD

BRSORD

Bristol

Mon 6/1

8:55 am-8:20 am

2 stops29h 25m

Chicago O'Hare Intl

Mon 6/8

3:45 pm-2:05 pm

1 stop16h 20m

$1,016

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 10/9

1:00 pm-9:45 pm

1 stop14h 45m

Chicago Midway

Wed 10/14

9:30 am-7:15 am

2 stops15h 45m

$1,028

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Tue 10/6

1:00 pm-9:45 pm

1 stop14h 45m

Chicago Midway

Sun 10/18

9:30 am-7:15 am

2 stops15h 45m

$1,029

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 10/5

1:00 pm-9:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/18

9:30 am-7:15 am

2 stops15h 45m

$1,032

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 60 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 17h 26m. KLM provides one of the quickest options available for as low as $984. The distance from Wales to Chicago is about 3855 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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