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$305+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Round-trip from

$649
(Mytrip)

One-way from

$338
(Kiwi.com)
From Wales to Chicago (CHI)
Search Deals
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 April 29, 2025.

This Mytrip deal was found by Cheapflights users on 4/28. 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.
Sat 6/76:15 pmMAN - ORD
2 stops24h 40mMultiple Airlines
Mon 6/237:05 pmORD - MAN
2 stops18h 35mMultiple Airlines
Deal found 4/28$649
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/107:10 pmMAN - ORD
1 stop27h 00mScandinavian Airlines
Sun 9/147:15 pmORD - MAN
1 stop32h 15mScandinavian Airlines
Deal found 4/27$656
This Netflights deal was found by Cheapflights users on 4/28. 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.
Mon 9/18:55 amMAN - ORD
1 stop13h 00mBritish Airways
Wed 9/2410:35 pmORD - MAN
1 stop11h 00mBritish Airways
Deal found 4/28$664
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:05 amMAN - ORD
2 stops14h 45mUnited Airlines
Wed 9/241:00 pmORD - MAN
2 stops15h 20mUnited Airlines
Deal found 4/27$692
This Netflights deal was found by Cheapflights users on 4/29. 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 9/2612:35 pmMAN - MDW
1 stop15h 09mVirgin Atlantic
Tue 9/301:00 pmMDW - MAN
2 stops15h 20mVirgin Atlantic
Deal found 4/29$709
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/106:15 amBRS - ORD
1 stop13h 55mDelta
Tue 5/1311:03 amORD - BRS
2 stops15h 47mDelta
Deal found 4/29$716
This Virgin Atlantic deal was found by Cheapflights users on 4/29. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/109:20 amBRS - ORD
1 stop10h 50mVirgin Atlantic
Tue 5/134:20 pmORD - BRS
1 stop14h 55mVirgin Atlantic
Deal found 4/29$717
This KLM deal was found by Cheapflights users on 4/29. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/109:20 amBRS - MDW
2 stops14h 27mKLM
Tue 5/131:08 pmMDW - BRS
2 stops13h 42mKLM
Deal found 4/29$722
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/115:55 amMAN - ORD
1 stop14h 15mDelta
Sun 5/187:00 amORD - MAN
1 stop18h 45mDelta
Deal found 4/27$725
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:55 amMAN - MDW
2 stops18h 41mDelta
Tue 9/305:59 pmMDW - MAN
2 stops13h 26mDelta
Deal found 4/29$729
This The Travel House deal was found by Cheapflights users on 4/28. 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 11/2911:55 amMAN - ORD
1 stop11h 25mIcelandair
Fri 12/126:30 pmORD - MAN
1 stop10h 15mIcelandair
Deal found 4/28$751
This EaseMyTrip deal was found by Cheapflights users on 4/28. 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 EaseMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/16:05 amMAN - ORD
2 stops14h 46mAir Canada
Fri 9/126:30 pmORD - MAN
1 stop9h 50mAir Canada
Deal found 4/28$771

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 April 29, 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 6/7

6:15 pm-12:55 pm

2 stops24h 40m

Chicago O'Hare Intl

Mon 6/23

7:05 pm-7:40 pm

2 stops18h 35m

$649

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 9/10

7:10 pm-4:10 pm

1 stop27h 00m

Chicago O'Hare Intl

Sun 9/14

7:15 pm-9:30 am

1 stop32h 15m

$656

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sat 5/10

7:00 am-2:40 pm

1 stop13h 40m

Chicago O'Hare Intl

Thu 5/15

7:10 pm-10:00 pm

1 stop20h 50m

$663

ManchesterChicago

MAN - ORD

MANORD

Manchester

Wed 9/17

6:05 am-2:50 pm

2 stops14h 45m

Chicago O'Hare Intl

Wed 9/24

1:00 pm-10:20 am

2 stops15h 20m

$692

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/26

12:35 pm-9:44 pm

1 stop15h 09m

Chicago Midway

Tue 9/30

1:00 pm-10:20 am

2 stops15h 20m

$709

BristolChicago

BRS - ORD

BRSORD

Bristol

Sat 5/10

6:15 am-2:10 pm

1 stop13h 55m

Chicago O'Hare Intl

Tue 5/13

11:03 am-8:50 am

2 stops15h 47m

$716

BristolChicago

BRS - ORD

BRSORD

Bristol

Sat 5/10

9:20 am-2:10 pm

1 stop10h 50m

Chicago O'Hare Intl

Tue 5/13

4:20 pm-1:15 pm

1 stop14h 55m

$717

BristolChicago

BRS - MDW

BRSMDW

Bristol

Sat 5/10

9:20 am-5:47 pm

2 stops14h 27m

Chicago Midway

Tue 5/13

1:08 pm-8:50 am

2 stops13h 42m

$722

ManchesterChicago

MAN - ORD

MANORD

Manchester

Sun 5/11

5:55 am-2:10 pm

1 stop14h 15m

Chicago O'Hare Intl

Sun 5/18

7:00 am-7:45 am

1 stop18h 45m

$725

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Fri 9/26

5:55 am-6:36 pm

2 stops18h 41m

Chicago Midway

Tue 9/30

5:59 pm-1:25 pm

2 stops13h 26m

$729

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 53 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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 29, 2025.
Read through reviews of airlines operating flights from Wales to Chicago, such as Delta, KLM and SWISS. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
SWISS
7.5
Good
1,588 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air France
7.4
Good
1,446 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines to fly from Wales to Chicago one-way?

    The cheapest airlines for a one-way flight from Wales to Chicago are Icelandair ($556), TAP AIR PORTUGAL ($624), and Aer Lingus ($728).

  • 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.

  • 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 Wales?

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