$403+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
Jul 28 — Aug 41
Round-trip
1 adult, Economy
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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 June 28, 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 June 28, 2026.
This deal was found by Cheapflights users on 6/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:05 pm
MAN
- ORD
1 stop14h 20m
Icelandair
Wed 10/147:25 pm
ORD
- MAN
1 stop10h 15m
Icelandair
Deal found 6/27![Icelandair logo]()
$630
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 10/298:00 am
MAN
- ORD
2 stops15h 20m
Multiple Airlines
Thu 11/126:30 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$645
This Mytrip deal was found by Cheapflights users on 6/28. 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.
Thu 9/106:00 am
MAN
- ORD
3 stops37h 23m
Multiple Airlines
Thu 9/247:25 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$647
This Mytrip deal was found by Cheapflights users on 6/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
MAN
- ORD
2 stops16h 57m
Multiple Airlines
Mon 8/317:25 pm
ORD
- MAN
2 stops20h 55m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$650
This Mytrip deal was found by Cheapflights users on 6/26. 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 8/187:30 am
MAN
- ORD
2 stops18h 22m
Multiple Airlines
Mon 8/317:25 pm
ORD
- MAN
2 stops20h 55m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$652
This Mytrip deal was found by Cheapflights users on 6/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:30 am
MAN
- ORD
2 stops18h 22m
Multiple Airlines
Sat 8/297:25 pm
ORD
- MAN
2 stops20h 35m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$657
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 9/81:50 pm
MAN
- ORD
2 stops34h 00m
Multiple Airlines
Sun 9/137:25 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$660
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:45 am
MAN
- ORD
2 stops15h 35m
Multiple Airlines
Sun 11/156:30 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$674
This Mytrip deal was found by Cheapflights users on 6/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:20 pm
BRS
- ORD
2 stops24h 37m
Multiple Airlines
Mon 9/710:25 pm
ORD
- BRS
2 stops18h 35m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$678
This Virgin Atlantic deal was found by Cheapflights users on 6/23. 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.
Thu 8/201:00 pm
MAN
- MDW
1 stop15h 36m
Virgin Atlantic
Thu 9/312:46 pm
MDW
- MAN
1 stop14h 04m
Virgin Atlantic
Deal found 6/23![Virgin Atlantic logo]()
$680
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 10/412:35 pm
MAN
- ORD
2 stops35h 15m
Multiple Airlines
Sun 10/257:30 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$684
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:20 pm
BRS
- ORD
2 stops31h 15m
Multiple Airlines
Mon 10/59:00 pm
ORD
- BRS
1 stop11h 25m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$698
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 June 28, 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 June 28, 2026.
This Virgin Atlantic deal was found by Cheapflights users on 6/23. 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.
Thu 8/201:00 pm
MAN
- MDW
1 stop15h 36m
Virgin Atlantic
Thu 9/312:46 pm
MDW
- MAN
1 stop14h 04m
Virgin Atlantic
Deal found 6/23![Virgin Atlantic logo]()
$680
This Scandinavian Airlines deal was found by Cheapflights users on 6/25. 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.
Mon 10/58:25 pm
MAN
- ORD
2 stops25h 45m
Scandinavian Airlines
Sun 10/187:15 pm
ORD
- MAN
2 stops18h 30m
Scandinavian Airlines
Deal found 6/25![Scandinavian Airlines logo]()
$747
This Lufthansa deal was found by Cheapflights users on 6/24. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:35 am
MAN
- ORD
1 stop13h 40m
Lufthansa
Mon 9/144:05 pm
ORD
- MAN
1 stop19h 05m
Lufthansa
Deal found 6/24![Lufthansa logo]()
$841
This KLM deal was found by Cheapflights users on 6/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:15 am
BRS
- ORD
1 stop14h 15m
KLM
Thu 10/14:20 pm
ORD
- BRS
1 stop18h 40m
KLM
Deal found 6/27![KLM logo]()
$855
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 12/35:55 am
BRS
- ORD
1 stop14h 30m
Delta
Mon 12/1411:30 am
ORD
- BRS
2 stops16h 45m
Delta
Deal found 6/25![Delta logo]()
$865
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am
BRS
- ORD
2 stops16h 20m
Multiple Airlines
Wed 12/28:10 pm
ORD
- BRS
1 stop10h 55m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$868
This Booking.com deal was found by Cheapflights users on 6/23. 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 7/1312:05 pm
MAN
- ORD
1 stop13h 10m
Aer Lingus
Thu 7/163:45 pm
ORD
- MAN
1 stop10h 55m
Aer Lingus
Deal found 6/23![Aer Lingus logo]()
$889
This SWISS deal was found by Cheapflights users on 6/27. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/82:05 pm
MAN
- ORD
1 stop32h 15m
SWISS
Sat 11/146:50 pm
ORD
- MAN
1 stop12h 25m
SWISS
Deal found 6/27![SWISS logo]()
$965
This Scandinavian Airlines deal was found by Cheapflights users on 6/26. 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 9/47:10 pm
MAN
- ORD
1 stop27h 00m
Scandinavian Airlines
Mon 9/77:15 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$774
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 12/35:55 am
BRS
- ORD
2 stops20h 29m
Delta
Sun 12/131:30 pm
ORD
- BRS
2 stops14h 45m
Delta
Deal found 6/25![Delta logo]()
$870
This Mytrip deal was found by Cheapflights users on 6/26. 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 9/258:00 pm
BRS
- ORD
3 stops30h 12m
Multiple Airlines
Sun 10/410:25 pm
ORD
- BRS
2 stops18h 45m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$887
This KLM deal was found by Cheapflights users on 6/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:20 am
BRS
- ORD
1 stop10h 55m
KLM
Sat 10/34:20 pm
ORD
- BRS
1 stop23h 45m
KLM
Deal found 6/27![KLM logo]()
$895
This Scandinavian Airlines deal was found by Cheapflights users on 6/26. 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 9/39:35 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Wed 9/97:15 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$816
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:25 am
BRS
- ORD
1 stop11h 35m
Aer Lingus
Wed 12/28:10 pm
ORD
- BRS
1 stop12h 15m
Aer Lingus
Deal found 6/27![Aer Lingus logo]()
$902
This Delta deal was found by Cheapflights users on 6/27. 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.
Tue 9/156:15 am
BRS
- ORD
1 stop14h 00m
Delta
Tue 9/294:20 pm
ORD
- BRS
1 stop10h 30m
Delta
Deal found 6/27![Delta logo]()
$895
This KLM deal was found by Cheapflights users on 6/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:20 am
BRS
- MDW
2 stops14h 59m
KLM
Sat 10/31:19 pm
MDW
- BRS
2 stops14h 56m
KLM
Deal found 6/27![KLM logo]()
$900
This Scandinavian Airlines deal was found by Cheapflights users on 6/23. 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.
Sun 10/257:15 pm
MAN
- ORD
2 stops31h 18m
Scandinavian Airlines
Sun 11/17:15 pm
ORD
- MAN
2 stops19h 00m
Scandinavian Airlines
Deal found 6/23![Scandinavian Airlines logo]()
$819
This Mytrip deal was found by Cheapflights users on 6/23. 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 8/128:05 pm
BRS
- ORD
2 stops24h 50m
Multiple Airlines
Sun 8/237:25 pm
ORD
- BRS
2 stops21h 45m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$910
This Delta deal was found by Cheapflights users on 6/27. 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.
Mon 9/149:20 am
BRS
- MDW
2 stops14h 59m
Delta
Mon 10/51:19 pm
MDW
- BRS
2 stops13h 31m
Delta
Deal found 6/27![Delta logo]()
$900
This KLM deal was found by Cheapflights users on 6/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:45 pm
BRS
- MDW
2 stops15h 00m
KLM
Sat 10/37:13 pm
MDW
- BRS
2 stops15h 47m
KLM
Deal found 6/27![KLM logo]()
$900
This Scandinavian Airlines deal was found by Cheapflights users on 6/26. 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 9/39:35 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sun 9/67:15 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$856
This Delta deal was found by Cheapflights users on 6/27. 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.
Wed 9/169:20 am
BRS
- MDW
2 stops14h 59m
Delta
Sat 10/31:19 pm
MDW
- BRS
2 stops14h 56m
Delta
Deal found 6/27![Delta logo]()
$900
This Scandinavian Airlines deal was found by Cheapflights users on 6/26. 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.
Sun 8/309:35 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sun 9/67:15 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$856
This Mytrip deal was found by Cheapflights users on 6/24. 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 8/1211:15 pm
CWL
- MDW
3 stops40h 02m
Multiple Airlines
Wed 8/193:15 pm
MDW
- CWL
1 stop13h 00m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$1,071
This Delta deal was found by Cheapflights users on 6/27. 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.
Tue 9/156:15 am
BRS
- MDW
2 stops18h 04m
Delta
Fri 10/29:59 am
MDW
- BRS
2 stops18h 16m
Delta
Deal found 6/27![Delta logo]()
$900
This Scandinavian Airlines deal was found by Cheapflights users on 6/24. 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 9/49:35 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sun 9/67:15 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 6/24![Scandinavian Airlines logo]()
$858
This Delta deal was found by Cheapflights users on 6/27. 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.
Sat 9/1210:45 am
BRS
- ORD
1 stop33h 30m
Delta
Mon 10/54:50 pm
ORD
- BRS
1 stop14h 25m
Delta
Deal found 6/27![Delta logo]()
$934
This Mytrip deal was found by Cheapflights users on 6/26. 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 8/611:35 am
CWL
- ORD
1 stop14h 17m
Multiple Airlines
Sun 8/95:35 pm
ORD
- CWL
2 stops22h 10m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$1,143
This Scandinavian Airlines deal was found by Cheapflights users on 6/26. 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.
Mon 8/317:10 pm
MAN
- ORD
1 stop27h 00m
Scandinavian Airlines
Sat 9/57:15 pm
ORD
- MAN
1 stop17h 35m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$899
This KLM deal was found by Cheapflights users on 6/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:20 am
BRS
- MDW
2 stops14h 59m
KLM
Thu 10/11:00 pm
MDW
- BRS
2 stops13h 50m
KLM
Deal found 6/27![KLM logo]()
$1,247
Last-minute flights from Wales to ChicagoDiscover last-minute flight deals from Wales to Chicago. Data last updated June 28, 2026 and is based on user searches.
Discover last-minute flight deals from Wales to Chicago. Data last updated June 28, 2026 and is based on user searches.
This British Airways deal was found by Cheapflights users on 6/25. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:55 pm
BRS
- ORD
1 stop29h 05m
British Airways
Thu 7/93:45 pm
ORD
- BRS
1 stop10h 10m
British Airways
Deal found 6/25![British Airways logo]()
$907
This Delta deal was found by Cheapflights users on 6/25. 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 7/39:20 am
BRS
- ORD
1 stop10h 55m
Delta
Thu 7/95:54 pm
ORD
- BRS
2 stops17h 11m
Delta
Deal found 6/25![Delta logo]()
$984
This Mytrip deal was found by Cheapflights users on 6/28. 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.
Wed 7/87:05 am
MAN
- ORD
2 stops35h 35m
Multiple Airlines
Mon 7/207:25 pm
ORD
- MAN
2 stops16h 25m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$790
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:55 am
MAN
- MDW
2 stops22h 08m
Multiple Airlines
Mon 7/2012:11 pm
MDW
- MAN
1 stop14h 39m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$1,075
This Travcart deal was found by Cheapflights users on 6/27. 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 Travcart is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:40 am
MAN
- MDW
1 stop17h 35m
Virgin Atlantic
Tue 7/2112:41 pm
MDW
- MAN
1 stop14h 09m
Virgin Atlantic
Deal found 6/27![Virgin Atlantic logo]()
$1,232
This Virgin Atlantic deal was found by Cheapflights users on 6/24. 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.
Thu 7/168:55 am
MAN
- ORD
1 stop11h 20m
Virgin Atlantic
Sun 7/195:10 pm
ORD
- MAN
1 stop17h 45m
Virgin Atlantic
Deal found 6/24![Virgin Atlantic logo]()
$718
This Virgin Atlantic deal was found by Cheapflights users on 6/24. 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.
Thu 7/165:50 am
MAN
- MDW
2 stops22h 25m
Virgin Atlantic
Sun 7/1911:05 am
MDW
- MAN
1 stop14h 10m
Virgin Atlantic
Deal found 6/24![Virgin Atlantic logo]()
$863
This British Airways deal was found by Cheapflights users on 6/25. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:25 am
BRS
- ORD
1 stop11h 35m
British Airways
Sat 8/13:45 pm
ORD
- BRS
1 stop10h 10m
British Airways
Deal found 6/25![British Airways logo]()
$1,083
This Mytrip deal was found by Cheapflights users on 6/24. 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 7/227:55 am
MAN
- ORD
2 stops16h 20m
Multiple Airlines
Fri 7/317:25 pm
ORD
- MAN
2 stops21h 20m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$835
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 7/236:00 am
MAN
- ORD
1 stop14h 00m
Multiple Airlines
Thu 7/303:45 pm
ORD
- MAN
1 stop10h 55m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$819
This Mytrip deal was found by Cheapflights users on 6/26. 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 7/277:45 am
MAN
- ORD
2 stops19h 40m
Multiple Airlines
Mon 8/37:25 pm
ORD
- MAN
2 stops20h 55m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$822
This Mytrip deal was found by Cheapflights users on 6/25. 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 7/287:30 am
MAN
- ORD
2 stops16h 45m
Multiple Airlines
Mon 8/37:25 pm
ORD
- MAN
2 stops20h 55m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$816
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 June 28, 2026.
Search for one-way flight options from Wales to Chicago. Find affordable one-way fares based on user searches. Data last updated June 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/317:15 am
MAN
- ORD
3 stops40h 35m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 8/510:25 pm
MAN
- MDW
3 stops46h 10m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$409
This Mytrip deal was found by Cheapflights users on 6/28. 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.
Wed 8/1210:25 pm
MAN
- ORD
3 stops27h 27m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:40 pm
MAN
- ORD
3 stops33h 10m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/1911:15 pm
CWL
- ORD
3 stops27h 15m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/1911:15 pm
CWL
- MDW
3 stops45h 20m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$459
This Mytrip deal was found by Cheapflights users on 6/24. 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 8/510:25 pm
MAN
- ORD
3 stops29h 40m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:25 pm
MAN
- MDW
3 stops46h 10m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$488
This Mytrip deal was found by Cheapflights users on 6/24. 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 7/2210:25 pm
MAN
- ORD
3 stops29h 40m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$493
This Mytrip deal was found by Cheapflights users on 6/24. 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 7/810:25 pm
MAN
- ORD
3 stops29h 40m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$519
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 7/2810:45 pm
MAN
- MDW
3 stops45h 50m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:40 am
MAN
- ORD
3 stops32h 00m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$534
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 June 28, 2026.
Round-trip from | $630 |
|---|---|
One-way from | $403 (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 June 28, 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
Cheapest round-trip
ManchesterChicago
MAN - MDW
MANMDW
Manchester
Thu 8/20
1:00 pm-10:36 pm
1 stop15h 36m
Chicago Midway
Thu 9/3
12:46 pm-8:50 am
1 stop14h 04m
$680
ManchesterChicago
MAN - ORD
MANORD
Manchester
Mon 10/5
8:25 pm-4:10 pm
2 stops25h 45m
Chicago O'Hare Intl
Sun 10/18
7:15 pm-7:45 pm
2 stops18h 30m
$747
ManchesterChicago
MAN - ORD
MANORD
Manchester
Fri 9/4
7:10 pm-4:10 pm
1 stop27h 00m
Chicago O'Hare Intl
Mon 9/7
7:15 pm-6:30 pm
1 stop17h 15m
$774
ManchesterChicago
MAN - ORD
MANORD
Manchester
Thu 9/3
9:35 am-4:10 pm
1 stop12h 35m
Chicago O'Hare Intl
Wed 9/9
7:15 pm-6:30 pm
1 stop17h 15m
$816
ManchesterChicago
MAN - ORD
MANORD
Manchester
Sun 10/25
7:15 pm-9:33 pm
2 stops31h 18m
Chicago O'Hare Intl
Sun 11/1
7:15 pm-8:15 pm
2 stops19h 00m
$819
ManchesterChicago
MAN - ORD
MANORD
Manchester
Mon 9/7
10:35 am-6:15 pm
1 stop13h 40m
Chicago O'Hare Intl
Mon 9/14
4:05 pm-5:10 pm
1 stop19h 05m
$841
BristolChicago
BRS - ORD
BRSORD
Bristol
Mon 9/14
6:15 am-2:30 pm
1 stop14h 15m
Chicago O'Hare Intl
Thu 10/1
4:20 pm-5:00 pm
1 stop18h 40m
$855
ManchesterChicago
MAN - ORD
MANORD
Manchester
Thu 9/3
9:35 am-4:10 pm
1 stop12h 35m
Chicago O'Hare Intl
Sun 9/6
7:15 pm-6:30 pm
1 stop17h 15m
$856
ManchesterChicago
MAN - ORD
MANORD
Manchester
Sun 8/30
9:35 am-4:10 pm
1 stop12h 35m
Chicago O'Hare Intl
Sun 9/6
7:15 pm-6:30 pm
1 stop17h 15m
$856
ManchesterChicago
MAN - ORD
MANORD
Manchester
Fri 9/4
9:35 am-4:10 pm
1 stop12h 35m
Chicago O'Hare Intl
Sun 9/6
7:15 pm-6:30 pm
1 stop17h 15m
$858
Showing 1-10 of 48 resultsSorted by cheapest first
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
MAN-MDW
BRS-ORD
CWL-ORD
CWL-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
MAN-MDW
BRS-ORD
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?
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