$378+ Cheap flights from Chicago (CHI) to Portsmouth, England
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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LHR
Jun 17 — Jun 241
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Portsmouth 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
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Cheapest flights from Chicago to PortsmouthExplore the most affordable flight options available from Chicago to Portsmouth. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 2026.
Explore the most affordable flight options available from Chicago to Portsmouth. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 8/53:45 pm
ORD
- SOU
1 stop10h 55m
Multiple Airlines
Tue 8/252:15 pm
SOU
- ORD
2 stops30h 30m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$964
This KAYAK deal was found by Cheapflights users on 5/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:45 am
ORD
- SOU
2 stops14h 55m
Aer Lingus
Sun 8/239:20 am
SOU
- ORD
1 stop15h 55m
Aer Lingus
Deal found 5/13![Aer Lingus logo]()
$983
This Ovago deal was found by Cheapflights users on 5/13. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/63:45 pm
ORD
- SOU
1 stop19h 05m
Aer Lingus
Sat 8/229:20 am
SOU
- ORD
2 stops16h 32m
Aer Lingus
Deal found 5/13![Aer Lingus logo]()
$1,007
This KLM deal was found by Cheapflights users on 5/16. 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 8/254:20 pm
ORD
- SOU
1 stop10h 25m
KLM
Mon 9/75:20 pm
SOU
- ORD
1 stop26h 55m
KLM
Deal found 5/16![KLM logo]()
$1,009
This KAYAK deal was found by Cheapflights users on 5/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:39 am
ORD
- SOU
2 stops17h 01m
Multiple Airlines
Sun 8/239:20 am
SOU
- ORD
2 stops16h 14m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$1,010
This Ovago deal was found by Cheapflights users on 5/13. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/610:56 am
ORD
- SOU
2 stops15h 44m
Multiple Airlines
Sat 8/229:20 am
SOU
- ORD
2 stops16h 32m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$1,011
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 8/73:45 pm
ORD
- SOU
1 stop10h 55m
Multiple Airlines
Tue 8/252:15 pm
SOU
- ORD
2 stops30h 30m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$1,013
This Delta deal was found by Cheapflights users on 5/13. 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 10/116:45 pm
MDW
- SOU
2 stops16h 05m
Delta
Thu 10/155:20 pm
SOU
- MDW
2 stops29h 05m
Delta
Deal found 5/13![Delta logo]()
$1,026
This Delta deal was found by Cheapflights users on 5/13. 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 10/115:45 pm
ORD
- SOU
2 stops17h 05m
Delta
Thu 10/155:20 pm
SOU
- ORD
2 stops29h 13m
Delta
Deal found 5/13![Delta logo]()
$1,026
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 8/53:45 pm
ORD
- SOU
1 stop10h 55m
Multiple Airlines
Fri 8/218:10 pm
SOU
- ORD
2 stops49h 50m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$1,028
This Delta deal was found by Cheapflights users on 5/13. 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 8/59:59 am
MDW
- SOU
2 stops16h 46m
Delta
Tue 8/256:05 pm
SOU
- MDW
2 stops28h 10m
Delta
Deal found 5/13![Delta logo]()
$1,080
This KLM deal was found by Cheapflights users on 5/13. 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.
Fri 8/77:25 pm
MDW
- SOU
2 stops15h 35m
KLM
Mon 8/249:15 am
SOU
- MDW
2 stops14h 46m
KLM
Deal found 5/13![KLM logo]()
$1,180
Best flights from Chicago to PortsmouthDiscover carefully curated flight deals from Chicago to Portsmouth that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 18, 2026.
Discover carefully curated flight deals from Chicago to Portsmouth that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 18, 2026.
This KLM deal was found by Cheapflights users on 5/13. 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 9/74:50 pm
ORD
- SOU
1 stop18h 00m
KLM
Mon 9/215:20 pm
SOU
- ORD
1 stop26h 55m
KLM
Deal found 5/13![KLM logo]()
$1,011
This Delta deal was found by Cheapflights users on 5/13. 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 10/116:45 pm
MDW
- SOU
2 stops16h 05m
Delta
Thu 10/155:20 pm
SOU
- MDW
2 stops29h 05m
Delta
Deal found 5/13![Delta logo]()
$1,026
This Delta deal was found by Cheapflights users on 5/13. 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 8/57:25 pm
MDW
- SOU
2 stops16h 10m
Delta
Mon 8/246:05 pm
SOU
- MDW
2 stops29h 56m
Delta
Deal found 5/13![Delta logo]()
$1,080
This KLM deal was found by Cheapflights users on 5/13. 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 8/611:26 am
ORD
- SOU
2 stops15h 19m
KLM
Mon 8/246:05 pm
SOU
- ORD
1 stop26h 10m
KLM
Deal found 5/13![KLM logo]()
$1,120
This Delta deal was found by Cheapflights users on 5/13. 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 8/91:27 pm
MDW
- SOU
2 stops13h 18m
Delta
Tue 8/256:05 pm
SOU
- MDW
2 stops28h 10m
Delta
Deal found 5/13![Delta logo]()
$1,080
This KLM deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:27 pm
MDW
- SOU
2 stops13h 18m
KLM
Mon 8/249:15 am
SOU
- MDW
2 stops19h 21m
KLM
Deal found 5/13![KLM logo]()
$1,180
This Delta deal was found by Cheapflights users on 5/15. 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 7/54:20 pm
ORD
- SOU
1 stop10h 25m
Delta
Tue 7/146:05 pm
SOU
- ORD
1 stop26h 25m
Delta
Deal found 5/15![Delta logo]()
$1,216
This KLM deal was found by Cheapflights users on 5/17. 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 7/284:20 pm
ORD
- SOU
1 stop19h 15m
KLM
Sat 8/89:15 am
SOU
- ORD
1 stop11h 00m
KLM
Deal found 5/17![KLM logo]()
$1,229
This Delta deal was found by Cheapflights users on 5/15. 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 7/610:29 am
ORD
- SOU
2 stops16h 16m
Delta
Tue 7/149:15 am
SOU
- ORD
1 stop11h 00m
Delta
Deal found 5/15![Delta logo]()
$1,220
This KLM deal was found by Cheapflights users on 5/16. 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 7/2812:27 pm
ORD
- SOU
2 stops14h 18m
KLM
Sun 8/95:30 pm
SOU
- ORD
1 stop27h 00m
KLM
Deal found 5/16![KLM logo]()
$1,234
This Delta deal was found by Cheapflights users on 5/15. 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 7/64:50 pm
ORD
- SOU
1 stop18h 45m
Delta
Wed 7/159:15 am
SOU
- ORD
2 stops18h 37m
Delta
Deal found 5/15![Delta logo]()
$1,226
This KLM deal was found by Cheapflights users on 5/16. 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 7/2912:27 pm
ORD
- SOU
2 stops14h 18m
KLM
Sun 8/95:30 pm
SOU
- ORD
1 stop27h 00m
KLM
Deal found 5/16![KLM logo]()
$1,234
This Delta deal was found by Cheapflights users on 5/15. 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 7/810:00 am
ORD
- SOU
2 stops16h 45m
Delta
Wed 7/159:15 am
SOU
- ORD
2 stops18h 37m
Delta
Deal found 5/15![Delta logo]()
$1,231
This KLM deal was found by Cheapflights users on 5/13. 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 9/76:45 pm
MDW
- SOU
2 stops16h 05m
KLM
Mon 9/219:05 am
SOU
- MDW
2 stops18h 41m
KLM
Deal found 5/13![KLM logo]()
$1,264
This Delta deal was found by Cheapflights users on 5/17. 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 7/285:54 pm
ORD
- SOU
2 stops17h 41m
Delta
Sat 8/89:15 am
SOU
- ORD
1 stop11h 00m
Delta
Deal found 5/17![Delta logo]()
$1,234
This KLM deal was found by Cheapflights users on 5/15. 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 6/296:58 pm
MDW
- SOU
2 stops15h 52m
KLM
Mon 7/69:15 am
SOU
- MDW
2 stops15h 03m
KLM
Deal found 5/15![KLM logo]()
$1,510
This Delta deal was found by Cheapflights users on 5/15. 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 6/11:22 pm
MDW
- SOU
2 stops13h 13m
Delta
Thu 6/49:05 am
SOU
- MDW
2 stops15h 28m
Delta
Deal found 5/15![Delta logo]()
$1,967
This KLM deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:27 pm
MDW
- SOU
2 stops13h 18m
KLM
Sat 8/229:15 am
SOU
- MDW
2 stops19h 21m
KLM
Deal found 5/13![KLM logo]()
$2,311
This Delta deal was found by Cheapflights users on 5/13. 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 6/276:55 pm
MDW
- SOU
2 stops15h 55m
Delta
Sat 7/49:15 am
SOU
- MDW
2 stops14h 39m
Delta
Deal found 5/13![Delta logo]()
$2,243
This KLM deal was found by Cheapflights users on 5/13. 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.
Fri 8/77:25 pm
MDW
- SOU
2 stops15h 35m
KLM
Sat 8/229:15 am
SOU
- MDW
2 stops19h 21m
KLM
Deal found 5/13![KLM logo]()
$2,311
This KLM deal was found by Cheapflights users on 5/15. 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 7/2911:05 am
MDW
- SOU
2 stops15h 40m
KLM
Sun 8/99:15 am
SOU
- MDW
2 stops19h 21m
KLM
Deal found 5/15![KLM logo]()
$2,556
Last-minute flights from Chicago to PortsmouthDiscover last-minute flight deals from Chicago to Portsmouth. Data last updated May 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portsmouth. Data last updated May 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/15. 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 5/187:00 pm
ORD
- SOU
2 stops15h 50m
Delta
Fri 5/299:05 am
SOU
- ORD
1 stop11h 10m
Delta
Deal found 5/15![Delta logo]()
$1,318
This Delta deal was found by Cheapflights users on 5/15. 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 5/187:00 pm
ORD
- SOU
2 stops15h 50m
Delta
Tue 5/269:05 am
SOU
- ORD
2 stops17h 09m
Delta
Deal found 5/15![Delta logo]()
$1,328
This Delta deal was found by Cheapflights users on 5/15. 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 5/187:00 pm
ORD
- SOU
2 stops15h 50m
Delta
Sat 5/309:15 am
SOU
- ORD
1 stop11h 00m
Delta
Deal found 5/15![Delta logo]()
$1,378
This Delta deal was found by Cheapflights users on 5/15. 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 5/187:00 pm
ORD
- SOU
2 stops15h 50m
Delta
Sun 5/315:20 pm
SOU
- ORD
2 stops29h 31m
Delta
Deal found 5/15![Delta logo]()
$1,388
This Delta deal was found by Cheapflights users on 5/15. 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 5/2012:30 pm
ORD
- SOU
2 stops14h 05m
Delta
Mon 5/255:20 pm
SOU
- ORD
1 stop26h 55m
Delta
Deal found 5/15![Delta logo]()
$1,395
This Delta deal was found by Cheapflights users on 5/15. 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 6/11:22 pm
MDW
- SOU
2 stops13h 13m
Delta
Thu 6/49:05 am
SOU
- MDW
2 stops15h 28m
Delta
Deal found 5/15![Delta logo]()
$1,967
This KAYAK deal was found by Cheapflights users on 5/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2310:20 pm
ORD
- SOU
1 stop15h 10m
Aer Lingus
Thu 7/29:20 am
SOU
- ORD
1 stop15h 55m
Aer Lingus
Deal found 5/16![Aer Lingus logo]()
$1,356
This KAYAK deal was found by Cheapflights users on 5/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/239:00 pm
ORD
- SOU
1 stop16h 30m
Aer Lingus
Tue 7/75:20 pm
SOU
- ORD
1 stop31h 55m
Aer Lingus
Deal found 5/14![Aer Lingus logo]()
$1,370
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/273:45 pm
ORD
- SOU
1 stop10h 50m
Aer Lingus
Sat 7/48:00 pm
SOU
- ORD
1 stop21h 30m
Aer Lingus
Deal found 5/13![Aer Lingus logo]()
$1,371
This Cheapflightsfares deal was found by Cheapflights users on 5/15. 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 6/293:45 pm
ORD
- SOU
1 stop10h 55m
Aer Lingus
Mon 7/68:00 pm
SOU
- ORD
1 stop21h 30m
Aer Lingus
Deal found 5/15![Aer Lingus logo]()
$1,259
This Mytrip deal was found by Cheapflights users on 5/15. 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 6/292:15 pm
ORD
- SOU
2 stops23h 15m
Multiple Airlines
Mon 7/65:55 pm
SOU
- ORD
3 stops34h 10m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$1,273
This KLM deal was found by Cheapflights users on 5/15. 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 6/296:58 pm
MDW
- SOU
2 stops15h 52m
KLM
Mon 7/69:15 am
SOU
- MDW
2 stops15h 03m
KLM
Deal found 5/15![KLM logo]()
$1,510
One-way flights from Chicago to PortsmouthSearch for one-way flight options from Chicago to Portsmouth. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
Search for one-way flight options from Chicago to Portsmouth. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 8/410:25 pm
ORD
- SOU
2 stops30h 40m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 8/310:25 pm
ORD
- SOU
2 stops29h 50m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 5/17. 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 8/164:20 pm
ORD
- SOU
1 stop19h 15m
Delta
Deal found 5/17![Delta logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 8/27:25 pm
ORD
- SOU
3 stops31h 00m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 7/1110:25 am
MDW
- SOU
3 stops43h 25m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 5/17. 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 8/1712:46 pm
MDW
- SOU
2 stops22h 49m
Delta
Deal found 5/17![Delta logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 7/3110:25 pm
ORD
- SOU
2 stops29h 00m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 8/110:25 pm
ORD
- SOU
3 stops28h 15m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 5/17. 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 8/156:44 pm
ORD
- SOU
2 stops32h 01m
Delta
Deal found 5/17![Delta logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 8/23:45 pm
ORD
- SOU
1 stop10h 55m
Aer Lingus
Deal found 5/16![Aer Lingus logo]()
$438
This Delta deal was found by Cheapflights users on 5/17. 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 8/161:52 pm
MDW
- SOU
2 stops21h 43m
Delta
Deal found 5/17![Delta logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 8/410:25 am
MDW
- SOU
3 stops24h 25m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$521
Find flight deals from Chicago to Portsmouth
Keep the following information in mind while searching for Chicago to Portsmouth flight deals. Data was last updated May 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $964 (Kiwi.com) |
One-way from | $378 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $1,155 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Portsmouth 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 May 18, 2026.
Use the filters below to find and compare flights from Chicago to Portsmouth that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Mon 9/7
4:50 pm-4:50 pm
1 stop18h 00m
Southampton Eastleigh
Mon 9/21
5:20 pm-2:15 pm
1 stop26h 55m
$1,011
ChicagoSouthampton
MDW - SOU
MDWSOU
Chicago Midway
Sun 10/11
6:45 pm-4:50 pm
2 stops16h 05m
Southampton Eastleigh
Thu 10/15
5:20 pm-4:25 pm
2 stops29h 05m
$1,026
ChicagoSouthampton
MDW - SOU
MDWSOU
Chicago Midway
Wed 8/5
7:25 pm-5:35 pm
2 stops16h 10m
Southampton Eastleigh
Mon 8/24
6:05 pm-6:01 pm
2 stops29h 56m
$1,080
ChicagoSouthampton
MDW - SOU
MDWSOU
Chicago Midway
Sun 8/9
1:27 pm-8:45 am
2 stops13h 18m
Southampton Eastleigh
Tue 8/25
6:05 pm-4:15 pm
2 stops28h 10m
$1,080
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Thu 8/6
11:26 am-8:45 am
2 stops15h 19m
Southampton Eastleigh
Mon 8/24
6:05 pm-2:15 pm
1 stop26h 10m
$1,120
ChicagoSouthampton
MDW - SOU
MDWSOU
Chicago Midway
Sat 8/8
1:27 pm-8:45 am
2 stops13h 18m
Southampton Eastleigh
Mon 8/24
9:15 am-10:36 pm
2 stops19h 21m
$1,180
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Sun 7/5
4:20 pm-8:45 am
1 stop10h 25m
Southampton Eastleigh
Tue 7/14
6:05 pm-2:30 pm
1 stop26h 25m
$1,216
Quickest round-trip
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Mon 7/6
10:29 am-8:45 am
2 stops16h 16m
Southampton Eastleigh
Tue 7/14
9:15 am-2:15 pm
1 stop11h 00m
$1,220
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Mon 7/6
4:50 pm-5:35 pm
1 stop18h 45m
Southampton Eastleigh
Wed 7/15
9:15 am-9:52 pm
2 stops18h 37m
$1,226
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Tue 7/28
4:20 pm-5:35 pm
1 stop19h 15m
Southampton Eastleigh
Sat 8/8
9:15 am-2:15 pm
1 stop11h 00m
$1,229
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Chicago to Portsmouth
Have a flexible travel schedule? Discover the best time to fly to Portsmouth from Chicago with our price prediction graph.
ORD-SOU
MDW-SOU
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 Chicago to Portsmouth
CHI-P0R
ORD-SOU
MDW-SOU
What is the cheapest time of day to fly from CHI to P0R?
Find hourly flight availability from Chicago to Portsmouth. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 18, 2026.
When flying from Chicago to Portsmouth, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Chicago to Portsmouth
Explore weekly flight availability from Chicago to Portsmouth. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 18, 2026.
The most flights from CHI to P0R are scheduled on a Monday (58 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (30 on average).
How much does it cost to fly round-trip from Chicago to Portsmouth?
Reviews of airlines servicing Portsmouth
Get insights into the airlines that provide service to Portsmouth. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portsmouth. Reviews last updated May 18, 2026.
Peruse reviews from past customers who have flown with KLM and Aer Lingus from Chicago to Portsmouth to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.8
Comfort
7.7
Boarding
7.8
Food
7.3
Crew
8.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Apr 2026
OKC - ATL
Overall
7.8
Comfort
7.7
Boarding
7.8
Food
7.3
Crew
8.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Apr 2026
OKC - ATL
Overall
7.8
Comfort
7.7
Boarding
7.8
Food
7.3
Crew
8.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Apr 2026
OKC - ATL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Portsmouth. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Find flights from Chicago to Portsmouth, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Portsmouth flights
Browse other Chicago and Portsmouth flight options. Last updated on May 18, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Portsmouth
Discover the top 10 airlines that operate flights from Chicago to Portsmouth. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$51 | Average$240 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$321 | Average$581 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$428 | Average$689 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$465 | Average$682 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$516 | Average$845 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$522 | Average$809 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$527 | Average$760 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$562 | Average$761 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$568 | Average$861 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$574 | Average$810 | FlexibilityNo cancel fee | On-time69% |