$330+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CWL — CHI
May 11 — May 181
Round-trip
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 April 11, 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 April 11, 2026.
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:35 pm
MAN
- ORD
2 stops33h 40m
Multiple Airlines
Tue 4/217:25 pm
ORD
- MAN
2 stops18h 00m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$671
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:55 am
MAN
- ORD
2 stops16h 25m
Multiple Airlines
Tue 12/16:30 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$675
This Mytrip deal was found by Cheapflights users on 4/8. 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 4/168:55 pm
MAN
- ORD
2 stops25h 05m
Multiple Airlines
Fri 5/110:25 pm
ORD
- MAN
1 stop31h 15m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$686
This Trip.com deal was found by Cheapflights users on 4/8. 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 11/710:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sat 11/147:20 pm
ORD
- MAN
1 stop32h 10m
Scandinavian Airlines
Deal found 4/8![Scandinavian Airlines logo]()
$687
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:45 pm
MAN
- ORD
2 stops33h 15m
Multiple Airlines
Fri 4/2410:25 pm
ORD
- MAN
1 stop31h 15m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$689
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:35 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Sat 10/248:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 4/6![Scandinavian Airlines logo]()
$698
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 11/28:30 am
MAN
- ORD
2 stops14h 50m
Multiple Airlines
Sat 11/76:30 pm
ORD
- MAN
1 stop10h 15m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$708
This Cheapflightsfares deal was found by Cheapflights users on 4/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:10 am
MAN
- ORD
1 stop12h 35m
Scandinavian Airlines
Tue 12/17:20 pm
ORD
- MAN
1 stop17h 15m
Scandinavian Airlines
Deal found 4/10![Scandinavian Airlines logo]()
$710
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:35 pm
MAN
- ORD
2 stops27h 05m
Multiple Airlines
Mon 5/189:55 am
ORD
- MAN
2 stops30h 25m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$711
This Trip.com deal was found by Cheapflights users on 4/8. 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.
Wed 4/298:25 am
BRS
- ORD
1 stop16h 50m
Aer Lingus
Tue 6/29:00 pm
ORD
- BRS
1 stop13h 00m
Aer Lingus
Deal found 4/8![Aer Lingus logo]()
$762
This Trip.com deal was found by Cheapflights users on 4/8. 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.
Wed 4/298:25 am
BRS
- ORD
2 stops15h 50m
Multiple Airlines
Tue 6/27:25 pm
ORD
- BRS
2 stops14h 35m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$828
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:45 am
BRS
- ORD
3 stops42h 11m
Multiple Airlines
Wed 5/209:55 am
ORD
- BRS
3 stops22h 40m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$857
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 April 11, 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 April 11, 2026.
This Trip.com deal was found by Cheapflights users on 4/8. 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.
Wed 4/298:25 am
BRS
- ORD
1 stop16h 50m
Aer Lingus
Tue 6/29:00 pm
ORD
- BRS
1 stop13h 00m
Aer Lingus
Deal found 4/8![Aer Lingus logo]()
$762
This Mytrip deal was found by Cheapflights users on 4/8. 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 4/2911:45 am
BRS
- ORD
3 stops31h 20m
Multiple Airlines
Tue 6/29:55 am
ORD
- BRS
3 stops24h 40m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$866
This Scandinavian Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:25 pm
MAN
- ORD
2 stops31h 31m
Scandinavian Airlines
Fri 5/297:00 am
ORD
- MAN
2 stops19h 55m
Scandinavian Airlines
Deal found 4/7![Scandinavian Airlines logo]()
$941
This Gotogate deal was found by Cheapflights users on 4/8. 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.
Wed 5/139:20 am
BRS
- ORD
1 stop11h 10m
Virgin Atlantic
Tue 5/194:20 pm
ORD
- BRS
1 stop23h 45m
Virgin Atlantic
Deal found 4/8![Virgin Atlantic logo]()
$951
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:55 am
MAN
- MDW
2 stops18h 36m
Delta
Mon 9/146:45 pm
MDW
- MAN
2 stops16h 00m
Delta
Deal found 4/6![Delta logo]()
$966
This KLM deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/225:15 pm
CWL
- ORD
1 stop27h 00m
KLM
Tue 7/74:20 pm
ORD
- CWL
1 stop10h 55m
KLM
Deal found 4/6![KLM logo]()
$1,013
This TAP AIR PORTUGAL deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:55 pm
MAN
- ORD
1 stop28h 05m
TAP AIR PORTUGAL
Wed 7/294:40 pm
ORD
- MAN
1 stop18h 25m
TAP AIR PORTUGAL
Deal found 4/6![TAP AIR PORTUGAL logo]()
$1,018
This Turkish Airlines deal was found by Cheapflights users on 4/9. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2611:30 pm
MAN
- ORD
1 stop16h 10m
Turkish Airlines
Mon 7/611:25 am
ORD
- MAN
1 stop16h 10m
Turkish Airlines
Deal found 4/9![Turkish Airlines logo]()
$1,051
This British Airways deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:55 pm
BRS
- ORD
2 stops34h 30m
British Airways
Tue 5/129:00 pm
ORD
- BRS
1 stop13h 00m
British Airways
Deal found 4/7![British Airways logo]()
$1,091
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:55 am
MAN
- ORD
1 stop15h 00m
United Airlines
Tue 6/26:30 am
ORD
- MAN
2 stops21h 20m
United Airlines
Deal found 4/10![United Airlines logo]()
$1,096
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:20 am
BRS
- ORD
2 stops16h 20m
Multiple Airlines
Wed 5/209:55 am
ORD
- BRS
3 stops22h 40m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$895
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:55 am
MAN
- ORD
2 stops16h 41m
Delta
Thu 9/171:30 pm
ORD
- MAN
2 stops14h 50m
Delta
Deal found 4/6![Delta logo]()
$966
This KLM deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/225:15 pm
CWL
- ORD
1 stop27h 00m
KLM
Mon 7/611:30 am
ORD
- CWL
2 stops15h 45m
KLM
Deal found 4/6![KLM logo]()
$1,013
This oojo deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:25 am
BRS
- ORD
1 stop16h 50m
Aer Lingus
Sat 5/29:00 pm
ORD
- BRS
1 stop13h 00m
Aer Lingus
Deal found 4/7![Aer Lingus logo]()
$1,034
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:45 am
BRS
- ORD
3 stops42h 11m
Multiple Airlines
Tue 5/193:45 pm
ORD
- BRS
2 stops22h 45m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$943
This TravelUp deal was found by Cheapflights users on 4/9. 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.
Sun 5/249:50 am
CWL
- MDW
2 stops38h 43m
Virgin Atlantic
Sun 5/311:22 pm
MDW
- CWL
2 stops13h 53m
Virgin Atlantic
Deal found 4/9![Virgin Atlantic logo]()
$1,076
This Delta deal was found by Cheapflights users on 4/9. 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 9/165:55 am
MAN
- MDW
2 stops18h 36m
Delta
Wed 9/239:30 am
MDW
- MAN
2 stops16h 45m
Delta
Deal found 4/9![Delta logo]()
$981
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
MAN
- ORD
1 stop14h 55m
United Airlines
Mon 6/16:00 am
ORD
- MAN
2 stops29h 10m
United Airlines
Deal found 4/10![United Airlines logo]()
$1,098
This Mytrip deal was found by Cheapflights users on 4/8. 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 5/237:30 am
CWL
- ORD
3 stops45h 45m
Multiple Airlines
Sat 5/309:55 am
ORD
- CWL
2 stops29h 25m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$970
This TravelUp deal was found by Cheapflights users on 4/9. 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 5/136:15 am
BRS
- ORD
1 stop14h 15m
KLM
Tue 5/194:20 pm
ORD
- BRS
1 stop10h 30m
KLM
Deal found 4/9![KLM logo]()
$1,080
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:55 am
MAN
- ORD
1 stop20h 00m
United Airlines
Thu 5/2812:53 pm
ORD
- MAN
2 stops15h 32m
United Airlines
Deal found 4/6![United Airlines logo]()
$1,121
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:45 am
CWL
- ORD
2 stops18h 03m
Delta
Tue 7/710:28 am
ORD
- CWL
2 stops16h 47m
Delta
Deal found 4/7![Delta logo]()
$1,021
This Virgin Atlantic deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:00 pm
MAN
- MDW
1 stop14h 46m
Virgin Atlantic
Tue 9/1510:35 am
MDW
- MAN
1 stop16h 15m
Virgin Atlantic
Deal found 4/6![Virgin Atlantic logo]()
$1,176
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/245:55 am
BRS
- ORD
1 stop14h 05m
Multiple Airlines
Sun 5/319:00 pm
ORD
- BRS
1 stop11h 15m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$997
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:10 am
MAN
- ORD
2 stops16h 26m
Delta
Fri 9/181:15 pm
ORD
- MAN
2 stops15h 05m
Delta
Deal found 4/6![Delta logo]()
$1,053
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:55 am
MAN
- ORD
2 stops16h 52m
United Airlines
Fri 5/2911:03 am
ORD
- MAN
2 stops17h 22m
United Airlines
Deal found 4/7![United Airlines logo]()
$1,168
This TravelUp deal was found by Cheapflights users on 4/10. 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 8/269:45 am
CWL
- ORD
1 stop10h 45m
Multiple Airlines
Wed 9/91:30 pm
ORD
- CWL
2 stops13h 45m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$1,004
This Expedia deal was found by Cheapflights users on 4/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:15 pm
CWL
- MDW
2 stops30h 41m
KLM
Sun 5/317:13 pm
MDW
- CWL
2 stops32h 02m
KLM
Deal found 4/10![KLM logo]()
$1,238
This TravelUp deal was found by Cheapflights users on 4/10. 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.
Tue 9/159:45 am
CWL
- MDW
2 stops18h 01m
Virgin Atlantic
Thu 10/15:25 pm
MDW
- CWL
2 stops33h 50m
Virgin Atlantic
Deal found 4/10![Virgin Atlantic logo]()
$1,255
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:15 pm
CWL
- ORD
2 stops28h 10m
Multiple Airlines
Thu 10/19:00 pm
ORD
- CWL
1 stop19h 20m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$1,013
Last-minute flights from Wales to ChicagoDiscover last-minute flight deals from Wales to Chicago. Data last updated April 11, 2026 and is based on user searches.
Discover last-minute flight deals from Wales to Chicago. Data last updated April 11, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/8. 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 4/168:55 pm
MAN
- ORD
2 stops25h 05m
Multiple Airlines
Fri 5/110:25 pm
ORD
- MAN
1 stop31h 15m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$686
This Mytrip deal was found by Cheapflights users on 4/9. 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 4/168:15 am
MAN
- ORD
2 stops31h 25m
Multiple Airlines
Thu 4/2311:25 am
ORD
- MAN
2 stops31h 25m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$739
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:35 pm
MAN
- ORD
2 stops33h 40m
Multiple Airlines
Tue 4/217:25 pm
ORD
- MAN
2 stops18h 00m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$671
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:45 pm
MAN
- ORD
2 stops33h 15m
Multiple Airlines
Fri 4/2410:25 pm
ORD
- MAN
1 stop31h 15m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$689
This Trip.com deal was found by Cheapflights users on 4/8. 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.
Wed 4/298:25 am
BRS
- ORD
1 stop16h 50m
Aer Lingus
Tue 6/29:00 pm
ORD
- BRS
1 stop13h 00m
Aer Lingus
Deal found 4/8![Aer Lingus logo]()
$762
This Trip.com deal was found by Cheapflights users on 4/8. 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.
Wed 4/298:25 am
BRS
- ORD
2 stops15h 50m
Multiple Airlines
Tue 6/27:25 pm
ORD
- BRS
2 stops14h 35m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$828
This Mytrip deal was found by Cheapflights users on 4/9. 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 5/84:20 pm
MAN
- ORD
2 stops29h 50m
Multiple Airlines
Sat 5/1612:59 pm
ORD
- MAN
3 stops29h 11m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$771
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:35 pm
MAN
- ORD
2 stops27h 05m
Multiple Airlines
Mon 5/189:55 am
ORD
- MAN
2 stops30h 25m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$711
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:45 am
BRS
- ORD
3 stops42h 11m
Multiple Airlines
Wed 5/209:55 am
ORD
- BRS
3 stops22h 40m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$857
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:45 am
BRS
- ORD
3 stops41h 30m
Multiple Airlines
Wed 5/209:55 am
ORD
- BRS
3 stops22h 40m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$896
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:25 pm
MAN
- ORD
2 stops31h 45m
Multiple Airlines
Thu 5/287:15 pm
ORD
- MAN
2 stops21h 20m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$773
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/237:45 am
BRS
- ORD
1 stop12h 15m
Multiple Airlines
Sat 5/309:00 pm
ORD
- BRS
1 stop11h 30m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$886
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 April 11, 2026.
Search for one-way flight options from Wales to Chicago. Find affordable one-way fares based on user searches. Data last updated April 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:45 pm
MAN
- ORD
2 stops45h 57m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:45 pm
MAN
- MDW
3 stops53h 46m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:35 am
MAN
- ORD
3 stops44h 38m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:45 pm
MAN
- MDW
3 stops44h 00m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:35 am
MAN
- MDW
3 stops35h 37m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 6/37:45 pm
MAN
- ORD
2 stops28h 30m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/296:55 pm
MAN
- ORD
2 stops51h 05m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$414
This Mytrip deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:25 pm
MAN
- ORD
2 stops27h 15m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/67:55 am
MAN
- ORD
3 stops45h 43m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:25 am
MAN
- ORD
3 stops36h 50m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/211:35 pm
MAN
- ORD
2 stops32h 25m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:05 pm
BRS
- ORD
2 stops23h 20m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$427
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 April 11, 2026.
Round-trip from | $689 (Mytrip) |
|---|---|
One-way from | $330 (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 April 11, 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
BristolChicago
BRS - ORD
BRSORD
Bristol
Wed 4/29
8:25 am-7:15 pm
1 stop16h 50m
Chicago O'Hare Intl
Tue 6/2
9:00 pm-4:00 pm
1 stop13h 00m
$762
BristolChicago
BRS - ORD
BRSORD
Bristol
Wed 4/29
11:45 am-1:05 pm
3 stops31h 20m
Chicago O'Hare Intl
Tue 6/2
9:55 am-4:35 pm
3 stops24h 40m
$866
BristolChicago
BRS - ORD
BRSORD
Bristol
Wed 5/13
9:20 am-7:40 pm
2 stops16h 20m
Chicago O'Hare Intl
Wed 5/20
9:55 am-2:35 pm
3 stops22h 40m
$895
ManchesterChicago
MAN - ORD
MANORD
Manchester
Fri 5/22
8:25 pm-9:56 pm
2 stops31h 31m
Chicago O'Hare Intl
Fri 5/29
7:00 am-8:55 am
2 stops19h 55m
$941
BristolChicago
BRS - ORD
BRSORD
Bristol
Wed 5/13
11:45 am-11:56 pm
3 stops42h 11m
Chicago O'Hare Intl
Tue 5/19
3:45 pm-8:30 pm
2 stops22h 45m
$943
BristolChicago
BRS - ORD
BRSORD
Bristol
Wed 5/13
9:20 am-2:30 pm
1 stop11h 10m
Chicago O'Hare Intl
Tue 5/19
4:20 pm-10:05 pm
1 stop23h 45m
$951
ManchesterChicago
MAN - MDW
MANMDW
Manchester
Mon 9/7
5:55 am-6:31 pm
2 stops18h 36m
Chicago Midway
Mon 9/14
6:45 pm-4:45 pm
2 stops16h 00m
$966
ManchesterChicago
MAN - ORD
MANORD
Manchester
Wed 9/9
5:55 am-4:36 pm
2 stops16h 41m
Chicago O'Hare Intl
Thu 9/17
1:30 pm-10:20 am
2 stops14h 50m
$966
CardiffChicago
CWL - ORD
CWLORD
Cardiff Wales
Sat 5/23
7:30 am-11:15 pm
3 stops45h 45m
Chicago O'Hare Intl
Sat 5/30
9:55 am-9:20 pm
2 stops29h 25m
$970
ManchesterChicago
MAN - MDW
MANMDW
Manchester
Wed 9/16
5:55 am-6:31 pm
2 stops18h 36m
Chicago Midway
Wed 9/23
9:30 am-8:15 am
2 stops16h 45m
$981
Showing 1-10 of 57 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.
BRS-ORD
MAN-ORD
MAN-MDW
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
BRS-ORD
MAN-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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights