$266+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
Mar 2 — Mar 91
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Wales to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Wales to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Wales to ChicagoExplore 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 January 31, 2026.
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 January 31, 2026.
This Gotogate deal was found by Cheapflights users on 1/31. 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.
Sat 2/2110:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Mon 3/98:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 1/31![Scandinavian Airlines logo]()
$539
This Mytrip deal was found by Cheapflights users on 1/31. 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.
Tue 3/1711:55 am
MAN
- ORD
2 stops17h 27m
Multiple Airlines
Tue 3/246:10 pm
ORD
- MAN
3 stops35h 50m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$556
This Booking.com deal was found by Cheapflights users on 1/31. 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 3/411:55 am
MAN
- ORD
2 stops18h 45m
Multiple Airlines
Tue 3/105:15 am
ORD
- MAN
3 stops24h 30m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$562
This Scandinavian Airlines deal was found by Cheapflights users on 1/30. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Mon 3/27:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 1/30![Scandinavian Airlines logo]()
$565
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Mon 4/207:15 pm
ORD
- MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$567
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Mon 4/207:15 pm
ORD
- MAN
2 stops34h 50m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$571
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Sat 4/257:15 pm
ORD
- MAN
2 stops18h 15m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$575
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1110:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sun 2/157:10 pm
ORD
- MAN
1 stop17h 25m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$576
This Mytrip deal was found by Cheapflights users on 1/30. 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 2/2711:50 am
BRS
- ORD
1 stop13h 25m
Multiple Airlines
Fri 3/69:00 pm
ORD
- BRS
1 stop16h 40m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$726
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:25 am
BRS
- ORD
1 stop15h 30m
Multiple Airlines
Sun 3/224:50 pm
ORD
- BRS
1 stop9h 45m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$766
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Wed 3/119:00 am
BRS
- ORD
1 stop14h 55m
Multiple Airlines
Tue 3/174:45 pm
ORD
- BRS
1 stop9h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$774
This Travcart deal was found by Cheapflights users on 1/29. 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 Travcart is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:30 pm
MAN
- MDW
1 stop14h 01m
Virgin Atlantic
Tue 3/176:07 pm
MDW
- MAN
1 stop11h 23m
Virgin Atlantic
Deal found 1/29![Virgin Atlantic logo]()
$780
Best flights from Wales to ChicagoDiscover carefully curated flight deals from Wales to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 31, 2026.
Discover carefully curated flight deals from Wales to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 31, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sat 4/257:15 pm
ORD
- MAN
1 stop17h 35m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$567
This TAP AIR PORTUGAL deal was found by Cheapflights users on 1/29. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 pm
MAN
- ORD
1 stop28h 00m
TAP AIR PORTUGAL
Sat 5/96:15 pm
ORD
- MAN
1 stop33h 50m
TAP AIR PORTUGAL
Deal found 1/29![TAP AIR PORTUGAL logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:25 am
BRS
- ORD
1 stop15h 30m
Multiple Airlines
Sun 3/224:50 pm
ORD
- BRS
1 stop9h 45m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$766
This Travcart deal was found by Cheapflights users on 1/29. 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 Travcart is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:30 pm
MAN
- MDW
1 stop14h 01m
Virgin Atlantic
Tue 3/176:07 pm
MDW
- MAN
1 stop11h 23m
Virgin Atlantic
Deal found 1/29![Virgin Atlantic logo]()
$780
This lastminute.com deal was found by Cheapflights users on 1/31. 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 3/178:20 am
BRS
- ORD
1 stop11h 50m
Aer Lingus
Tue 3/248:40 pm
ORD
- BRS
1 stop13h 40m
Aer Lingus
Deal found 1/31![Aer Lingus logo]()
$785
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:35 pm
BRS
- ORD
1 stop26h 45m
KLM
Tue 3/245:50 pm
ORD
- BRS
2 stops14h 20m
KLM
Deal found 1/31![KLM logo]()
$843
This Delta deal was found by Cheapflights users on 1/29. 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.
Wed 3/111:30 pm
MAN
- MDW
1 stop14h 01m
Delta
Tue 3/176:34 pm
MDW
- MAN
2 stops16h 31m
Delta
Deal found 1/29![Delta logo]()
$844
This Scandinavian Airlines deal was found by Cheapflights users on 1/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2610:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Mon 3/27:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 1/28![Scandinavian Airlines logo]()
$567
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Mon 4/207:15 pm
ORD
- MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$567
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2010:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Mon 4/207:15 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$567
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/208:55 pm
MAN
- ORD
2 stops25h 50m
Scandinavian Airlines
Sat 4/257:15 pm
ORD
- MAN
1 stop17h 35m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$571
This Travcart deal was found by Cheapflights users on 1/31. 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 Travcart is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:30 pm
MAN
- MDW
1 stop14h 01m
Virgin Atlantic
Tue 3/246:07 pm
MDW
- MAN
1 stop11h 23m
Virgin Atlantic
Deal found 1/31![Virgin Atlantic logo]()
$804
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 3/126:55 am
BRS
- ORD
1 stop17h 00m
Multiple Airlines
Tue 3/174:45 pm
ORD
- BRS
1 stop9h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$811
This Delta deal was found by Cheapflights users on 1/31. 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 3/41:30 pm
MAN
- MDW
1 stop15h 01m
Delta
Tue 3/101:10 pm
MDW
- MAN
2 stops16h 20m
Delta
Deal found 1/31![Delta logo]()
$845
This KLM deal was found by Cheapflights users on 1/30. 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.
Mon 3/165:15 pm
CWL
- ORD
2 stops28h 28m
KLM
Mon 3/235:25 pm
ORD
- CWL
1 stop11h 25m
KLM
Deal found 1/30![KLM logo]()
$847
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:50 am
BRS
- ORD
1 stop13h 25m
Aer Lingus
Fri 3/63:50 pm
ORD
- BRS
1 stop10h 05m
Aer Lingus
Deal found 1/31![Aer Lingus logo]()
$866
This Travcart deal was found by Cheapflights users on 1/31. 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 Travcart is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:30 pm
MAN
- MDW
1 stop34h 15m
Virgin Atlantic
Tue 3/1012:47 pm
MDW
- MAN
1 stop16h 43m
Virgin Atlantic
Deal found 1/31![Virgin Atlantic logo]()
$804
This Booking.com deal was found by Cheapflights users on 1/31. 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 3/178:20 am
BRS
- ORD
2 stops15h 00m
Multiple Airlines
Tue 3/247:30 pm
ORD
- BRS
2 stops14h 30m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$823
This Delta deal was found by Cheapflights users on 1/31. 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.
Tue 3/175:50 am
MAN
- MDW
2 stops17h 04m
Delta
Tue 3/249:35 am
MDW
- MAN
2 stops16h 05m
Delta
Deal found 1/31![Delta logo]()
$847
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:40 pm
BRS
- ORD
1 stop30h 40m
KLM
Wed 3/115:25 pm
ORD
- BRS
1 stop10h 00m
KLM
Deal found 1/30![KLM logo]()
$847
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 3/147:50 am
BRS
- ORD
1 stop16h 05m
Multiple Airlines
Tue 3/174:45 pm
ORD
- BRS
1 stop9h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$843
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:55 am
BRS
- MDW
2 stops14h 45m
KLM
Tue 3/241:10 pm
MDW
- BRS
2 stops14h 15m
KLM
Deal found 1/31![KLM logo]()
$848
This Virgin Atlantic deal was found by Cheapflights users on 1/30. 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.
Mon 3/168:40 pm
MAN
- MDW
2 stops25h 42m
Virgin Atlantic
Mon 3/231:10 pm
MDW
- MAN
2 stops16h 00m
Virgin Atlantic
Deal found 1/30![Virgin Atlantic logo]()
$852
This Delta deal was found by Cheapflights users on 1/29. 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 3/75:50 am
MAN
- MDW
2 stops16h 24m
Delta
Tue 3/102:05 pm
MDW
- MAN
2 stops15h 05m
Delta
Deal found 1/29![Delta logo]()
$887
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 3/144:40 pm
BRS
- ORD
2 stops28h 05m
Multiple Airlines
Wed 3/184:50 pm
ORD
- BRS
1 stop10h 05m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$872
This Delta deal was found by Cheapflights users on 1/30. 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 3/118:55 am
BRS
- MDW
2 stops14h 45m
Delta
Mon 3/161:10 pm
MDW
- BRS
2 stops19h 00m
Delta
Deal found 1/30![Delta logo]()
$894
This KLM deal was found by Cheapflights users on 1/30. 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.
Thu 3/128:55 am
BRS
- MDW
2 stops14h 45m
KLM
Tue 3/176:34 pm
MDW
- BRS
2 stops13h 36m
KLM
Deal found 1/30![KLM logo]()
$894
This Delta deal was found by Cheapflights users on 1/30. 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 3/118:55 am
BRS
- MDW
2 stops14h 45m
Delta
Wed 3/189:35 am
MDW
- BRS
2 stops17h 50m
Delta
Deal found 1/30![Delta logo]()
$894
This KLM deal was found by Cheapflights users on 1/30. 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.
Thu 3/126:00 am
BRS
- MDW
2 stops16h 54m
KLM
Mon 3/166:34 pm
MDW
- BRS
2 stops13h 36m
KLM
Deal found 1/30![KLM logo]()
$894
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BRS
- MDW
2 stops17h 37m
Multiple Airlines
Wed 3/111:10 pm
MDW
- BRS
2 stops14h 15m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$952
Last-minute flights from Wales to ChicagoDiscover last-minute flight deals from Wales to Chicago. Data last updated January 31, 2026 and is based on user searches.
Discover last-minute flight deals from Wales to Chicago. Data last updated January 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/97:55 am
BRS
- ORD
1 stop14h 50m
Multiple Airlines
Wed 2/187:20 pm
ORD
- BRS
1 stop13h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$882
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1110:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sun 2/157:10 pm
ORD
- MAN
1 stop17h 25m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$576
This Travcart deal was found by Cheapflights users on 1/30. 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 Travcart is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:25 pm
MAN
- MDW
1 stop15h 06m
Virgin Atlantic
Wed 2/1812:45 pm
MDW
- MAN
1 stop14h 00m
Virgin Atlantic
Deal found 1/30![Virgin Atlantic logo]()
$891
This Delta deal was found by Cheapflights users on 1/29. 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 2/131:25 pm
MAN
- MDW
1 stop15h 06m
Delta
Wed 2/189:34 am
MDW
- MAN
2 stops17h 11m
Delta
Deal found 1/29![Delta logo]()
$945
This Trip.com deal was found by Cheapflights users on 1/31. 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.
Mon 2/165:50 am
MAN
- MDW
2 stops18h 50m
KLM
Sat 2/2811:45 am
MDW
- MAN
2 stops14h 35m
KLM
Deal found 1/31![KLM logo]()
$986
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Sat 4/257:15 pm
ORD
- MAN
1 stop31h 40m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$567
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:55 pm
MAN
- ORD
2 stops32h 50m
Scandinavian Airlines
Mon 4/207:15 pm
ORD
- MAN
2 stops34h 50m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$579
This Scandinavian Airlines deal was found by Cheapflights users on 1/29. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Mon 4/207:15 pm
ORD
- MAN
2 stops34h 50m
Scandinavian Airlines
Deal found 1/29![Scandinavian Airlines logo]()
$571
This Gotogate deal was found by Cheapflights users on 1/31. 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.
Sat 2/2110:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Mon 3/98:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 1/31![Scandinavian Airlines logo]()
$539
This Scandinavian Airlines deal was found by Cheapflights users on 1/30. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:15 pm
MAN
- ORD
1 stop27h 30m
Scandinavian Airlines
Mon 3/27:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 1/30![Scandinavian Airlines logo]()
$565
This Mytrip deal was found by Cheapflights users on 1/30. 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 2/2711:50 am
BRS
- ORD
1 stop13h 25m
Multiple Airlines
Fri 3/69:00 pm
ORD
- BRS
1 stop16h 40m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$726
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:50 am
BRS
- ORD
1 stop13h 25m
Aer Lingus
Fri 3/63:50 pm
ORD
- BRS
1 stop10h 05m
Aer Lingus
Deal found 1/31![Aer Lingus logo]()
$866
One-way flights from Wales to ChicagoSearch for one-way flight options from Wales to Chicago. Find affordable one-way fares based on user searches. Data last updated January 31, 2026.
Search for one-way flight options from Wales to Chicago. Find affordable one-way fares based on user searches. Data last updated January 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:55 pm
MAN
- ORD
2 stops49h 05m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:55 pm
MAN
- MDW
2 stops49h 05m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:05 am
BRS
- ORD
3 stops46h 10m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:30 am
MAN
- ORD
3 stops39h 20m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 6/17:45 am
MAN
- ORD
2 stops19h 40m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 5/2210:45 pm
CWL
- ORD
2 stops25h 30m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 5/2210:45 pm
CWL
- MDW
3 stops39h 57m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$521
This Connections by easyJet deal was found by Cheapflights users on 1/30. 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 Connections by easyJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:25 am
MAN
- ORD
1 stop17h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:10 am
BRS
- MDW
3 stops42h 37m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:55 pm
MAN
- ORD
2 stops29h 20m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$591
This Icelandair deal was found by Cheapflights users on 1/30. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:05 pm
MAN
- ORD
1 stop11h 10m
Icelandair
Deal found 1/30![Icelandair logo]()
$619
This Delta deal was found by Cheapflights users on 1/29. 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.
Sun 4/1911:15 am
MAN
- MDW
1 stop17h 13m
Delta
Deal found 1/29![Delta logo]()
$636
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 January 31, 2026.
Round-trip from | $562 (Booking.com) |
|---|---|
One-way from | $266 (Kiwi.com) |
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 January 31, 2026.
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
Wed 2/25
10:10 am-4:45 pm
1 stop12h 35m
Chicago O'Hare Intl
Sat 4/25
7:15 pm-6:50 pm
1 stop17h 35m
$567
ManchesterChicago
MAN - ORD
MANORD
Manchester
Thu 2/26
10:10 am-4:45 pm
1 stop12h 35m
Chicago O'Hare Intl
Mon 3/2
7:20 pm-6:35 pm
1 stop17h 15m
$567
ManchesterChicago
MAN - ORD
MANORD
Manchester
Sat 2/21
10:10 am-4:45 pm
1 stop12h 35m
Chicago O'Hare Intl
Mon 4/20
7:15 pm-8:55 am
1 stop31h 40m
$567
ManchesterChicago
MAN - ORD
MANORD
Manchester
Fri 2/20
10:10 am-4:45 pm
1 stop12h 35m
Chicago O'Hare Intl
Mon 4/20
7:15 pm-6:30 pm
1 stop17h 15m
$567
ManchesterChicago
MAN - ORD
MANORD
Manchester
Tue 4/28
6:00 pm-4:00 pm
1 stop28h 00m
Chicago O'Hare Intl
Sat 5/9
6:15 pm-10:05 am
1 stop33h 50m
$571
ManchesterChicago
MAN - ORD
MANORD
Manchester
Fri 2/20
8:55 pm-4:45 pm
2 stops25h 50m
Chicago O'Hare Intl
Sat 4/25
7:15 pm-6:50 pm
1 stop17h 35m
$571
BristolChicago
BRS - ORD
BRSORD
Bristol
Sun 3/15
8:25 am-6:55 pm
1 stop15h 30m
Chicago O'Hare Intl
Sun 3/22
4:50 pm-7:35 am
1 stop9h 45m
$766
ManchesterChicago
MAN - MDW
MANMDW
Manchester
Wed 3/11
1:30 pm-10:31 pm
1 stop14h 01m
Chicago Midway
Tue 3/17
6:07 pm-10:30 am
1 stop11h 23m
$780
BristolChicago
BRS - ORD
BRSORD
Bristol
Tue 3/17
8:20 am-3:10 pm
1 stop11h 50m
Chicago O'Hare Intl
Tue 3/24
8:40 pm-3:20 pm
1 stop13h 40m
$785
ManchesterChicago
MAN - MDW
MANMDW
Manchester
Tue 3/17
1:30 pm-10:31 pm
1 stop14h 01m
Chicago Midway
Tue 3/24
6:07 pm-10:30 am
1 stop11h 23m
$804
Showing 1-10 of 50 results
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.
MAN-ORD
BRS-ORD
MAN-MDW
CWL-ORD
BRS-MDW
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
GBWLS-CHI
MAN-ORD
BRS-ORD
MAN-MDW
CWL-ORD
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor