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Cheap flights from Portsmouth to Chicago from £435

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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
7 Dec — 14 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 7 November 2025.

Sun 21/1218:05SOU - ORD
3 stops29h 15mMultiple Airlines
Sun 28/1218:30ORD - SOU
2 stops19h 10mMultiple Airlines
Deal found 6/11£710
Sun 21/1220:10SOU - ORD
1 stop23h 50mAer Lingus
Sun 28/1215:50ORD - SOU
1 stop10h 55mAer Lingus
Deal found 6/11£805
Sun 21/1218:05SOU - MDW
2 stops29h 14mMultiple Airlines
Sun 28/1218:08MDW - SOU
2 stops32h 02mMultiple Airlines
Deal found 6/11£962
Thu 6/1119:55SOU - ORD
2 stops23h 55mBritish Airways
Sat 26/920:50ORD - SOU
1 stop16h 40mBritish Airways
Deal found 6/11£1,388

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 7 November 2025.

Round-trip from

£661

One-way from

£435

Popular in

July

Cheapest in

February

Average price

£492
Virgin Atlantic
  • Virgin Atlantic
  • 5/3-9/3
  • 3 total stops
  • 47h 30m total
  • Portsmouth to Chicago
Search Deals
British Airways
  • British Airways
  • 11/3
  • 1 total stop
  • 11h 30m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£62 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
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 7 November 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

Thu 5/3

18:05-14:20

1 stop26h 15m

Chicago O'Hare Intl

Mon 9/3

17:25-17:00

1 stop18h 35m

£661

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 5/3

18:05-17:45

2 stops29h 40m

Chicago Midway

Mon 9/3

17:25-17:00

2 stops18h 35m

£667

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 21/12

18:05-17:20

3 stops29h 15m

Chicago O'Hare Intl

Sun 28/12

18:30-19:40

2 stops19h 10m

£710

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 25/1

09:30-20:00

2 stops16h 30m

Chicago O'Hare Intl

Mon 2/2

17:10-16:00

2 stops16h 50m

£733

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 21/12

18:05-17:19

2 stops29h 14m

Chicago Midway

Sun 28/12

18:08-08:10

2 stops32h 02m

£962

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 11/3

12:25-18:55

1 stop11h 30m

£435

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sat 31/1

09:30-20:00

2 stops16h 30m

£504

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 12/3

09:30-18:55

1 stop14h 25m

£505

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 31/12

12:25-17:55

1 stop11h 30m

£810

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 18/12

19:55-18:45

2 stops28h 50m

£1,063

Flights are sorted by cheapest return flights first.

Deals found on 6/11

Showing 1-10 of 13 results
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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, March is the cheapest month in which you can book a flight from Portsmouth to Chicago (average of £309). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £514). 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 7 November 2025.

It’s optimal to fly from Portsmouth to Chicago in the afternoon. By choosing this option you can save up to 5% on the cost of your flight, compared to a flight in the evening.

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 Thursday afternoons when fares are most often at their lowest. Saturday afternoons 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 7 November 2025.

The most flights from P0R to CHI are scheduled on a Thursday (42 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (29 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 £661, Virgin Atlantic can have you in Chicago from Portsmouth in 26h 15m. The distance from Portsmouth to Chicago is about 3921 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 (84%), Austrian Airlines (84%) or United Airlines (84%) 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 £1,300 for a flight from Portsmouth to Chicago. The cheapest flight overall is £372 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £684.

  • 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, March is the cheapest month in which you can book a flight from Portsmouth to Chicago (average of £309). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £514). 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 7 November 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest£322Average£499FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Virgin AtlanticCheapest£354Average£572FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
Scandinavian AirlinesCheapest£369Average£492FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£378Average£626FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Aer LingusCheapest£379Average£604FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
Brussels AirlinesCheapest£396Average£554FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
LufthansaCheapest£406Average£590FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
British AirwaysCheapest£414Average£582FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Austrian AirlinesCheapest£414Average£617FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
United AirlinesCheapest£418Average£555FlexibilityNo 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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