$352+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LHR
Mar 31 — Apr 71
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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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 Chicago to Portsmouth
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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 March 1, 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 March 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Tue 4/143:45 pm
ORD
- SOU
1 stop10h 20m
Aer Lingus
Tue 4/219:10 am
SOU
- ORD
1 stop16h 05m
Aer Lingus
Deal found 2/28![Aer Lingus logo]()
$724
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/124:20 pm
ORD
- SOU
1 stop10h 15m
Delta
Thu 4/235:20 pm
SOU
- ORD
1 stop26h 55m
Delta
Deal found 2/28![Delta logo]()
$809
This KLM deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/314:20 pm
ORD
- SOU
1 stop10h 15m
KLM
Tue 4/75:20 pm
SOU
- ORD
1 stop27h 10m
KLM
Deal found 3/1![KLM logo]()
$811
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:55 am
ORD
- SOU
2 stops25h 55m
Delta
Tue 4/215:20 pm
SOU
- ORD
1 stop27h 10m
Delta
Deal found 2/28![Delta logo]()
$814
This Delta deal was found by Cheapflights users on 2/27. 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.
Sun 8/94:20 pm
ORD
- SOU
1 stop10h 25m
Delta
Tue 8/259:15 am
SOU
- ORD
2 stops35h 43m
Delta
Deal found 2/27![Delta logo]()
$819
This Delta deal was found by Cheapflights users on 2/27. 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 8/107:00 am
ORD
- SOU
2 stops19h 45m
Delta
Tue 8/259:15 am
SOU
- ORD
2 stops35h 43m
Delta
Deal found 2/27![Delta logo]()
$824
This KLM deal was found by Cheapflights users on 2/26. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:50 pm
ORD
- SOU
1 stop18h 00m
KLM
Sat 10/105:20 pm
SOU
- ORD
1 stop26h 55m
KLM
Deal found 2/26![KLM logo]()
$839
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/124:20 pm
ORD
- SOU
1 stop10h 15m
Delta
Sun 4/199:15 am
SOU
- ORD
1 stop11h 00m
Delta
Deal found 2/28![Delta logo]()
$859
This KLM deal was found by Cheapflights users on 2/27. 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 4/134:50 pm
ORD
- SOU
1 stop18h 00m
KLM
Mon 4/205:20 pm
SOU
- ORD
1 stop26h 55m
KLM
Deal found 2/27![KLM logo]()
$862
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:21 pm
MDW
- SOU
2 stops17h 29m
Delta
Tue 4/219:05 am
SOU
- MDW
2 stops15h 31m
Delta
Deal found 2/28![Delta logo]()
$969
This Delta deal was found by Cheapflights users on 2/27. 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.
Thu 12/36:00 am
MDW
- SOU
2 stops20h 05m
Delta
Fri 12/118:40 am
SOU
- MDW
2 stops15h 30m
Delta
Deal found 2/27![Delta logo]()
$1,189
This KLM deal was found by Cheapflights users on 2/27. 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 4/137:16 pm
MDW
- SOU
2 stops15h 34m
KLM
Mon 4/209:05 am
SOU
- MDW
2 stops15h 31m
KLM
Deal found 2/27![KLM logo]()
$1,300
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 March 1, 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 March 1, 2026.
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:09 pm
ORD
- SOU
2 stops15h 41m
Delta
Thu 4/235:20 pm
SOU
- ORD
1 stop26h 55m
Delta
Deal found 2/28![Delta logo]()
$814
This KLM deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Sun 4/510:40 am
ORD
- SOU
2 stops15h 55m
KLM
Mon 5/45:20 pm
SOU
- ORD
1 stop26h 55m
KLM
Deal found 3/1![KLM logo]()
$816
This oojo deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/3110:40 pm
ORD
- SOU
2 stops36h 10m
Aer Lingus
Tue 4/78:00 pm
SOU
- ORD
2 stops30h 00m
Aer Lingus
Deal found 3/1![Aer Lingus logo]()
$1,022
This KLM deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/317:14 pm
ORD
- SOU
2 stops15h 36m
KLM
Tue 4/75:20 pm
SOU
- ORD
1 stop27h 10m
KLM
Deal found 3/1![KLM logo]()
$816
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/124:20 pm
ORD
- SOU
1 stop10h 15m
Delta
Fri 4/245:20 pm
SOU
- ORD
1 stop26h 55m
Delta
Deal found 2/28![Delta logo]()
$859
This Ovago deal was found by Cheapflights users on 2/27. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/231:00 pm
MDW
- SOU
2 stops13h 35m
Multiple Airlines
Fri 7/35:20 pm
SOU
- MDW
2 stops31h 11m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$1,849
This Delta deal was found by Cheapflights users on 2/27. 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 8/111:30 pm
ORD
- SOU
2 stops22h 05m
Delta
Sun 8/235:30 pm
SOU
- ORD
1 stop27h 00m
Delta
Deal found 2/27![Delta logo]()
$864
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:10 am
ORD
- SOU
2 stops19h 35m
Delta
Thu 4/235:20 pm
SOU
- ORD
1 stop26h 55m
Delta
Deal found 2/28![Delta logo]()
$922
This KLM deal was found by Cheapflights users on 2/26. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:50 pm
ORD
- SOU
1 stop18h 45m
KLM
Sun 8/95:30 pm
SOU
- ORD
1 stop27h 00m
KLM
Deal found 2/26![KLM logo]()
$1,079
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:21 pm
MDW
- SOU
2 stops17h 29m
Delta
Tue 4/219:05 am
SOU
- MDW
2 stops15h 31m
Delta
Deal found 2/28![Delta logo]()
$969
This KLM deal was found by Cheapflights users on 2/26. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:40 am
ORD
- SOU
2 stops16h 05m
KLM
Sun 8/95:30 pm
SOU
- ORD
1 stop27h 00m
KLM
Deal found 2/26![KLM logo]()
$1,084
This Delta deal was found by Cheapflights users on 2/27. 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 8/110:40 am
ORD
- SOU
2 stops16h 05m
Delta
Sat 8/229:15 am
SOU
- ORD
2 stops18h 51m
Delta
Deal found 2/27![Delta logo]()
$1,039
This KLM deal was found by Cheapflights users on 2/27. 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 4/137:16 pm
MDW
- SOU
2 stops15h 34m
KLM
Mon 4/209:05 am
SOU
- MDW
2 stops15h 31m
KLM
Deal found 2/27![KLM logo]()
$1,300
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/104:50 pm
ORD
- SOU
1 stop18h 00m
Delta
Wed 6/175:20 pm
SOU
- ORD
1 stop26h 55m
Delta
Deal found 2/26![Delta logo]()
$1,080
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:34 pm
MDW
- SOU
2 stops16h 16m
Delta
Sat 4/189:15 am
SOU
- MDW
2 stops15h 21m
Delta
Deal found 2/26![Delta logo]()
$2,595
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:30 am
MDW
- SOU
2 stops17h 50m
Delta
Thu 4/29:05 am
SOU
- MDW
2 stops15h 35m
Delta
Deal found 2/26![Delta logo]()
$2,885
This KLM deal was found by Cheapflights users on 2/28. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/271:05 pm
MDW
- SOU
2 stops13h 40m
KLM
Sun 8/99:15 am
SOU
- MDW
2 stops14h 50m
KLM
Deal found 2/28![KLM logo]()
$4,290
This KLM deal was found by Cheapflights users on 2/27. 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 7/291:05 pm
MDW
- SOU
2 stops13h 40m
KLM
Sun 8/99:15 am
SOU
- MDW
2 stops18h 30m
KLM
Deal found 2/27![KLM logo]()
$4,707
Last-minute flights from Chicago to PortsmouthDiscover last-minute flight deals from Chicago to Portsmouth. Data last updated March 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portsmouth. Data last updated March 1, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 2/26. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:50 pm
ORD
- SOU
1 stop17h 45m
Aer Lingus
Wed 3/1112:25 pm
SOU
- ORD
1 stop11h 30m
Aer Lingus
Deal found 2/26![Aer Lingus logo]()
$1,010
This British Airways deal was found by Cheapflights users on 2/26. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:30 pm
ORD
- SOU
2 stops17h 00m
British Airways
Wed 3/1112:25 pm
SOU
- ORD
1 stop11h 30m
British Airways
Deal found 2/26![British Airways logo]()
$4,999
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:10 am
ORD
- SOU
2 stops20h 10m
Delta
Thu 4/29:05 am
SOU
- ORD
1 stop11h 10m
Delta
Deal found 2/26![Delta logo]()
$1,167
This Mytrip deal was found by Cheapflights users on 2/26. 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 3/2612:50 pm
ORD
- SOU
3 stops23h 40m
Multiple Airlines
Thu 4/26:50 am
SOU
- ORD
3 stops23h 32m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$1,326
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:30 am
MDW
- SOU
2 stops17h 50m
Delta
Thu 4/29:05 am
SOU
- MDW
2 stops15h 35m
Delta
Deal found 2/26![Delta logo]()
$2,885
This KLM deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/314:20 pm
ORD
- SOU
1 stop10h 15m
KLM
Tue 4/75:20 pm
SOU
- ORD
1 stop27h 10m
KLM
Deal found 3/1![KLM logo]()
$811
This oojo deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/3110:40 pm
ORD
- SOU
2 stops36h 10m
Aer Lingus
Tue 4/78:00 pm
SOU
- ORD
2 stops30h 00m
Aer Lingus
Deal found 3/1![Aer Lingus logo]()
$1,022
This Mytrip deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:05 am
ORD
- SOU
3 stops21h 00m
Multiple Airlines
Tue 4/76:10 pm
SOU
- ORD
3 stops30h 21m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$1,322
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 March 1, 2026.
Search for one-way flight options from Chicago to Portsmouth. Find affordable one-way fares based on user searches. Data last updated March 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Mon 5/257:25 pm
ORD
- SOU
2 stops16h 15m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 2/27. 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.
Sun 5/3110:25 pm
ORD
- SOU
3 stops58h 35m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Sun 5/3110:25 am
MDW
- SOU
3 stops40h 00m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Tue 5/2610:25 am
MDW
- SOU
3 stops40h 00m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Wed 5/2710:25 am
MDW
- SOU
3 stops40h 15m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Mon 5/2510:25 am
MDW
- SOU
3 stops39h 40m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Tue 5/267:25 pm
ORD
- SOU
3 stops31h 00m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Sat 5/3010:25 am
MDW
- SOU
2 stops40h 15m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$446
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Wed 5/277:25 pm
ORD
- SOU
3 stops31h 15m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/287:15 pm
ORD
- SOU
3 stops42h 15m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$449
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 March 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $724 (Kiwi.com) |
One-way from | $352 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $710 |
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 March 1, 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
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Tue 4/14
7:09 pm-4:50 pm
2 stops15h 41m
Southampton Eastleigh
Thu 4/23
5:20 pm-2:15 pm
1 stop26h 55m
$814
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Sun 4/5
10:40 am-8:35 am
2 stops15h 55m
Southampton Eastleigh
Mon 5/4
5:20 pm-2:15 pm
1 stop26h 55m
$816
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Tue 3/31
7:14 pm-4:50 pm
2 stops15h 36m
Southampton Eastleigh
Tue 4/7
5:20 pm-2:30 pm
1 stop27h 10m
$816
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Sun 4/12
4:20 pm-8:35 am
1 stop10h 15m
Southampton Eastleigh
Fri 4/24
5:20 pm-2:15 pm
1 stop26h 55m
$859
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Tue 8/11
1:30 pm-5:35 pm
2 stops22h 05m
Southampton Eastleigh
Sun 8/23
5:30 pm-2:30 pm
1 stop27h 00m
$864
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Fri 4/17
7:10 am-8:45 am
2 stops19h 35m
Southampton Eastleigh
Thu 4/23
5:20 pm-2:15 pm
1 stop26h 55m
$922
ChicagoSouthampton
MDW - SOU
MDWSOU
Chicago Midway
Tue 4/14
5:21 pm-4:50 pm
2 stops17h 29m
Southampton Eastleigh
Tue 4/21
9:05 am-6:36 pm
2 stops15h 31m
$969
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Tue 3/31
10:40 pm-4:50 pm
2 stops36h 10m
Southampton Eastleigh
Tue 4/7
8:00 pm-8:00 pm
2 stops30h 00m
$1,022
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Sat 8/1
10:40 am-8:45 am
2 stops16h 05m
Southampton Eastleigh
Sat 8/22
9:15 am-10:06 pm
2 stops18h 51m
$1,039
ChicagoSouthampton
ORD - SOU
ORDSOU
Chicago O'Hare Intl
Wed 7/29
4:50 pm-5:35 pm
1 stop18h 45m
Southampton Eastleigh
Sun 8/9
5:30 pm-2:30 pm
1 stop27h 00m
$1,079
Showing 1-10 of 32 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 month to book a flight from Chicago to Portsmouth?
Currently, June is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $62). Flying from Chicago to Portsmouth in July is currently the most expensive (average of $608). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 1, 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 March 1, 2026.
The most flights from CHI to P0R are scheduled on a Monday (45 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (45 on average).
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 March 1, 2026.
Peruse reviews from past customers who have flown with Delta, 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
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - 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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Alternative routes for Chicago to Portsmouth
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Complete your trip
Complete your trip to Portsmouth by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Portsmouth by cabin class
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 March 1, 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 March 1, 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 March 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$51 | Average$432 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$257 | Average$674 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$321 | Average$554 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$345 | Average$897 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$427 | Average$689 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$678 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$481 | Average$783 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$516 | Average$793 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$522 | Average$809 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$539 | Average$756 | FlexibilityNo cancel fee | On-time70% |