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Cheap flights from Portsmouth to Chicago from £498

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
18 Oct — 25 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Portsmouth to Chicago

Keep the following information in mind while searching for Portsmouth to Chicago flight deals. Data was last updated 18 September 2025.

Round-trip from

£498

Popular in

July

Cheapest in

February

Average price

£434
KLM
  • KLM
  • 31/10-7/11
  • 2 total stops
  • 37h 15m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£60 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£9 potential savings vs. average return price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Portsmouth to Chicago

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 18 September 2025.

Fri 31/1017:30SOU - ORD
1 stop26h 50mKLM
Fri 7/1116:25ORD - SOU
1 stop10h 25mKLM
Deal found 16/9£498
Wed 8/1009:20SOU - MDW
2 stops15h 05mKLM
Tue 14/1013:08MDW - SOU
2 stops13h 37mKLM
Deal found 17/9£504
Fri 3/1009:20SOU - ORD
2 stops20h 34mVirgin Atlantic
Tue 7/1016:15ORD - SOU
1 stop10h 30mVirgin Atlantic
Deal found 17/9£504
Fri 3/1009:20SOU - MDW
2 stops15h 15mKLM
Tue 7/1013:08MDW - SOU
2 stops13h 37mKLM
Deal found 17/9£511
Fri 3/1009:20SOU - ORD
2 stops14h 44mKLM
Tue 7/1011:23ORD - SOU
2 stops15h 22mKLM
Deal found 17/9£511
Fri 31/1008:40SOU - MDW
2 stops18h 34mDelta
Fri 7/1110:40MDW - SOU
2 stops16h 10mDelta
Deal found 16/9£512
Wed 8/1009:20SOU - ORD
2 stops17h 59mMultiple Airlines
Tue 14/1008:57ORD - SOU
2 stops17h 48mMultiple Airlines
Deal found 17/9£591
Fri 3/1009:40SOU - ORD
1 stop12h 05mMultiple Airlines
Tue 7/1021:15ORD - SOU
1 stop16h 15mMultiple Airlines
Deal found 17/9£602
Wed 8/1009:20SOU - ORD
1 stop11h 20mVirgin Atlantic
Tue 14/1016:15ORD - SOU
1 stop18h 45mVirgin Atlantic
Deal found 17/9£678
Fri 31/1014:25SOU - ORD
2 stops32h 20mMultiple Airlines
Fri 7/1119:20ORD - SOU
3 stops31h 25mMultiple Airlines
Deal found 16/9£756
Sat 27/1209:30SOU - ORD
1 stop14h 25mBritish Airways
Sat 17/121:00ORD - SOU
1 stop12h 35mBritish Airways
Deal found 16/9£846

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 18 September 2025.
Use the filters below to find and compare flights from Portsmouth to Chicago that are best for you.

Fly from

Portsmouth

Fly to

Chicago

Route

Depart

Return

Price

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 31/10

17:30-15:20

1 stop26h 50m

Chicago O'Hare Intl

Fri 7/11

16:25-08:50

1 stop10h 25m

£498

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 3/10

09:20-23:54

2 stops20h 34m

Chicago O'Hare Intl

Tue 7/10

16:15-08:45

1 stop10h 30m

£504

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 8/10

09:20-18:25

2 stops15h 05m

Chicago Midway

Tue 14/10

13:08-08:45

2 stops13h 37m

£504

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 8/10

09:20-21:19

2 stops17h 59m

Chicago O'Hare Intl

Tue 14/10

16:15-08:45

1 stop10h 30m

£504

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 3/10

09:20-18:35

2 stops15h 15m

Chicago Midway

Tue 7/10

13:08-08:45

2 stops13h 37m

£511

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 31/10

08:40-22:14

2 stops18h 34m

Chicago Midway

Fri 7/11

10:40-08:50

2 stops16h 10m

£512

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 5/3

18:05-14:20

1 stop26h 15m

Chicago O'Hare Intl

Mon 9/3

17:25-17:00

1 stop18h 35m

£534

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 5/3

18:05-18:34

2 stops30h 29m

Chicago Midway

Mon 9/3

09:30-08:10

2 stops17h 40m

£538

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Mon 22/12

12:05-17:55

2 stops35h 50m

£575

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 23/12

15:20-06:25

3 stops45h 05m

£657

Flights are sorted by cheapest return flights first.

Deals found on 16/9

Showing 1-10 of 15 results
1
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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 month to book a flight from Portsmouth to Chicago?

Currently, January is the cheapest month in which you can book a flight from Portsmouth to Chicago (average of £595). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £843). 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 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 18 September 2025.

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.

What is the cheapest day to fly from Portsmouth to Chicago?

Use this chart to determine the cheapest time to fly return from Portsmouth to Chicago. Price data was last updated on 16 December 2024.

Travellers seeking maximum savings on their Portsmouth to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 18 September 2025.

The most flights from P0R to CHI are scheduled on a Monday (53 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (47 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 £512, KLM can have you in Chicago from Portsmouth in 18h 34m. 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 Malaysia Airlines (79%), Air Canada (76%) or Austrian Airlines (76%) 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 £798 for a flight from Portsmouth to Chicago. The cheapest flight overall is £408 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £504.

  • 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.

  • What is the cheapest month to book a flight from Portsmouth to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Portsmouth to Chicago (average of £595). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £843). 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.

See more FAQs

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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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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 18 September 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest£307Average£477FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Scandinavian AirlinesCheapest£349Average£476FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£362Average£605FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Aer LingusCheapest£362Average£565FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
Virgin AtlanticCheapest£375Average£530FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
Brussels AirlinesCheapest£388Average£543FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
LufthansaCheapest£390Average£567FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Austrian AirlinesCheapest£395Average£564FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
British AirwaysCheapest£399Average£553FlexibilityNo cancel feeOn-time70%
Search British Airways flights
United AirlinesCheapest£403Average£535FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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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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