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Cheap flights from Portsmouth to Chicago from £521

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 26/8. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
2 Aug — 9 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Portsmouth to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Portsmouth to Chicago
Explore the most affordable flight options available from Portsmouth to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 July 2026.

Thu 26/1109:20
SOU
-
ORD
2 stops16h 00m
British Airways
Mon 30/1120:10
ORD
-
SOU
1 stop17h 20m
British Airways
Deal found 28/6£810
Wed 5/809:20
SOU
-
ORD
1 stop15h 55m
Aer Lingus
Wed 12/815:45
ORD
-
SOU
1 stop10h 55m
Aer Lingus
Deal found 29/6£826
Fri 31/718:05
SOU
-
MDW
2 stops34h 10m
Delta
Thu 6/812:46
MDW
-
SOU
2 stops13h 59m
Delta
Deal found 30/6£995
Sat 4/709:15
SOU
-
MDW
2 stops14h 39m
Delta
Mon 6/719:16
MDW
-
SOU
2 stops16h 19m
Delta
Deal found 30/6£1,222
Tue 11/809:15
SOU
-
MDW
2 stops14h 46m
KLM
Tue 25/810:54
MDW
-
SOU
2 stops15h 51m
KLM
Deal found 2/7£1,350
Wed 1/709:05
SOU
-
MDW
2 stops15h 13m
Virgin Atlantic
Sun 5/718:58
MDW
-
SOU
2 stops31h 47m
Virgin Atlantic
Deal found 30/6£1,378
Wed 5/809:15
SOU
-
MDW
2 stops19h 21m
KLM
Wed 12/819:25
MDW
-
SOU
2 stops16h 10m
KLM
Deal found 29/6£1,425
Sat 15/809:15
SOU
-
MDW
2 stops14h 46m
Delta
Sat 22/816:39
MDW
-
SOU
2 stops18h 21m
Delta
Deal found 1/7£1,489
Sun 2/809:15
SOU
-
MDW
2 stops15h 03m
KLM
Sun 9/813:25
MDW
-
SOU
2 stops13h 20m
KLM
Deal found 1/7£2,109

Find flight deals from Portsmouth to Chicago

Keep the following information in mind while searching for Portsmouth to Chicago flight deals. Data was last updated 3 July 2026.

Round-trip from

£706

One-way from

£521

Popular in

July

Cheapest in

February

Average price

£701
Delta
  • Delta
  • 16/9-21/9
  • 4 total stops
  • 30h 53m total
  • Portsmouth to Chicago
Search Deals
British Airways
  • British Airways
  • 26/8
  • 1 total stop
  • 15h 55m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (£80 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Portsmouth 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 858,174 searches. Data last updated 3 July 2026.
Use the filters below to find and compare flights from Portsmouth to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 26/11

09:20-19:20

2 stops16h 00m

Chicago O'Hare Intl

Mon 30/11

20:10-19:30

1 stop17h 20m

£810

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 31/7

18:05-22:15

2 stops34h 10m

Chicago Midway

Thu 6/8

12:46-08:45

2 stops13h 59m

£995

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Tue 11/8

09:15-18:01

2 stops14h 46m

Chicago Midway

Tue 25/8

10:54-08:45

2 stops15h 51m

£1,350

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 5/8

09:15-22:36

2 stops19h 21m

Chicago Midway

Wed 12/8

19:25-17:35

2 stops16h 10m

£1,425

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sat 15/8

09:15-18:01

2 stops14h 46m

Chicago Midway

Sat 22/8

16:39-17:00

2 stops18h 21m

£1,489
Fastest return journey

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 2/8

09:15-18:18

2 stops15h 03m

Chicago Midway

Sun 9/8

13:25-08:45

2 stops13h 20m

£2,109
Cheapest one-way

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 26/8

09:20-19:15

1 stop15h 55m

£521

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Mon 24/8

09:20-14:20

2 stops35h 00m

£549

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 6/8

20:00-18:33

3 stops28h 33m

£588

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 27/8

20:00-11:30

1 stop21h 30m

£593

Flights are sorted by cheapest return flights first.

Deals found on 1/7

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from Portsmouth to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Portsmouth with our price prediction graph.
Estimated return 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 Portsmouth to Chicago

What is the cheapest time of day to fly from P0R to CHI?

Find hourly flight availability from Portsmouth to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 July 2026.

When flying from Portsmouth to Chicago, 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 Portsmouth to Chicago

Explore weekly flight availability from Portsmouth to Chicago. 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 3 July 2026.

The most flights from P0R to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (44 on average).

Related info for your journey

Find useful and relevant information for your journey from Portsmouth to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portsmouth to Chicago?

    For as low as £1,350, British Airways can have you in Chicago from Portsmouth in 14h 46m. The distance from Portsmouth to Chicago is about 3924 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the most reliable airlines from Portsmouth to Chicago?

    Consider Air Canada (90%), Austrian Airlines (90%) or United Airlines (90%) when booking your flight. These represent the most reliable airlines when flying from Portsmouth to Chicago.

  • What are the cheapest flights from Portsmouth to Chicago?

    On average you can expect to pay £1,659 for a flight from Portsmouth to Chicago. The cheapest flight overall is £369 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £818.

  • Can I find deals for flights from Portsmouth to Chicago that include hotel bookings?

    Yes. In addition to deals on Portsmouth to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Portsmouth to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portsmouth to Chicago.

  • Can I find deals for business class flights from Portsmouth to Chicago?

    Yes. Cheapflights offers flight deals from Portsmouth to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Portsmouth to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Exeter to O'Hare Intl flights
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Edinburgh to Moline flights
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Grimsby to St. Louis flights

Top 10 airlines flying from Portsmouth to Chicago

Discover the top 10 airlines that operate flights from Portsmouth to Chicago. 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 858,174 searches. Data last updated 3 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£304Average£600FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
IcelandairCheapest£351Average£494FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£366Average£664FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
Scandinavian AirlinesCheapest£377Average£534FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£389Average£552FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Brussels AirlinesCheapest£397Average£618FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
British AirwaysCheapest£414Average£657FlexibilityNo cancel feeOn-time70%
Search British Airways flights
LufthansaCheapest£419Average£631FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
FinnairCheapest£430Average£681FlexibilityNo cancel feeOn-time76%
Search Finnair flights
United AirlinesCheapest£432Average£673FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Portsmouth to Chicago?

Deals for Portsmouth to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Portsmouth to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Portsmouth to Chicago.

Can Cheapflights find flights from Portsmouth to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Portsmouth? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Portsmouth to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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