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$393+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$634
(Trip.com)

One-way from

$393
(Kiwi.com)
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 June 12, 2025.

This Trip.com deal was found by Cheapflights users on 6/10. 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.
Sat 9/61:40 pmBRS - ORD
2 stops34h 35mMultiple Airlines
Sat 9/137:25 pmORD - BRS
2 stops17h 10mMultiple Airlines
Deal found 6/10$634
This TravelUp deal was found by Cheapflights users on 6/10. 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 TravelUp is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:15 amBRS - ORD
1 stop14h 25mKLM
Wed 9/244:50 pmORD - BRS
1 stop10h 00mKLM
Deal found 6/10$653
This Trip.com deal was found by Cheapflights users on 6/10. 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.
Sat 9/61:40 pmBRS - ORD
1 stop30h 20mAer Lingus
Sat 9/139:15 pmORD - BRS
1 stop12h 45mAer Lingus
Deal found 6/10$654
This TravelUp deal was found by Cheapflights users on 6/10. 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 TravelUp is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:15 amBRS - MDW
2 stops18h 21mKLM
Wed 9/245:59 pmMDW - BRS
2 stops17h 01mKLM
Deal found 6/10$665
This Netflights deal was found by Cheapflights users on 6/11. 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 9/225:55 amMAN - MDW
2 stops18h 41mVirgin Atlantic
Mon 9/299:30 amMDW - MAN
2 stops21h 55mVirgin Atlantic
Deal found 6/11$667
This Netflights deal was found by Cheapflights users on 6/11. 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 9/15:55 amMAN - ORD
1 stop14h 45mVirgin Atlantic
Wed 9/2410:35 amORD - MAN
2 stops15h 45mVirgin Atlantic
Deal found 6/11$667
This Mytrip deal was found by Cheapflights users on 6/12. 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 8/78:50 amMAN - ORD
1 stop11h 10mMultiple Airlines
Sun 8/173:45 pmORD - MAN
1 stop10h 25mMultiple Airlines
Deal found 6/12$671
This Flightnetwork deal was found by Cheapflights users on 6/11. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:50 amMAN - ORD
1 stop11h 43mAir Canada
Thu 9/188:25 pmORD - MAN
1 stop31h 55mAir Canada
Deal found 6/11$675
This Gotogate deal was found by Cheapflights users on 6/10. 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.
Fri 10/38:25 pmMAN - ORD
2 stops25h 45mScandinavian Airlines
Sun 10/57:15 pmORD - MAN
2 stops18h 30mScandinavian Airlines
Deal found 6/10$676
This Netflights deal was found by Cheapflights users on 6/10. 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 9/17:00 amMAN - ORD
1 stop12h 50mBritish Airways
Fri 9/1210:35 pmORD - MAN
1 stop12h 45mBritish Airways
Deal found 6/10$681
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 9/39:20 amBRS - ORD
1 stop11h 20mDelta
Wed 9/1010:15 amORD - BRS
2 stops16h 35mDelta
Deal found 6/11$681
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 11/35:55 amMAN - MDW
2 stops18h 41mDelta
Mon 12/15:59 pmMDW - MAN
2 stops15h 56mDelta
Deal found 6/11$682

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 June 12, 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

Sat 9/6

1:40 pm-6:15 pm

2 stops34h 35m

Chicago O'Hare Intl

Sat 9/13

7:25 pm-6:35 pm

2 stops17h 10m

$634

BristolChicago

BRS - ORD

BRSORD

Bristol

Wed 9/17

6:15 am-2:40 pm

1 stop14h 25m

Chicago O'Hare Intl

Wed 9/24

4:50 pm-8:50 am

1 stop10h 00m

$653

BristolChicago

BRS - ORD

BRSORD

Bristol

Sat 9/6

1:40 pm-2:00 pm

1 stop30h 20m

Chicago O'Hare Intl

Sat 9/13

9:15 pm-4:00 pm

1 stop12h 45m

$654

BristolChicago

BRS - MDW

BRSMDW

Bristol

Wed 9/17

6:15 am-6:36 pm

2 stops18h 21m

Chicago Midway

Wed 9/24

5:59 pm-5:00 pm

2 stops17h 01m

$665

ManchesterChicago

MAN - MDW

MANMDW

Manchester

Mon 9/22

5:55 am-6:36 pm

2 stops18h 41m

Chicago Midway

Mon 9/29

9:30 am-1:25 pm

2 stops21h 55m

$667

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 9/1

5:55 am-2:40 pm

1 stop14h 45m

Chicago O'Hare Intl

Wed 9/24

10:35 am-8:20 am

2 stops15h 45m

$667

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 8/7

8:50 am-2:00 pm

1 stop11h 10m

Chicago O'Hare Intl

Sun 8/17

3:45 pm-8:10 am

1 stop10h 25m

$671

ManchesterChicago

MAN - ORD

MANORD

Manchester

Thu 9/11

11:50 am-5:33 pm

1 stop11h 43m

Chicago O'Hare Intl

Thu 9/18

8:25 pm-10:20 am

1 stop31h 55m

$675

ManchesterChicago

MAN - ORD

MANORD

Manchester

Fri 10/3

8:25 pm-4:10 pm

2 stops25h 45m

Chicago O'Hare Intl

Sun 10/5

7:15 pm-7:45 pm

2 stops18h 30m

$676

ManchesterChicago

MAN - ORD

MANORD

Manchester

Mon 9/1

7:00 am-1:50 pm

1 stop12h 50m

Chicago O'Hare Intl

Fri 9/12

10:35 pm-5:20 pm

1 stop12h 45m

$681

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 47 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 June 12, 2025.
Read through reviews of airlines operating flights from Wales to Chicago, such as Delta, KLM and Austrian Airlines. 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
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Austrian Airlines
7.6
Good
802 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Finnair
7.6
Good
1,290 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,463 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 ($603), British Airways ($661), and Aer Lingus ($711).

  • 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
Lansing
Benton Harbor
Porter
Hammond
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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