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Cheap flights from Portsmouth to Chicago from £329

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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Portsmouth to Chicago

Enter your travel dates to find the best prices.

Best flights from Portsmouth to Chicago
Discover carefully curated flight deals from Portsmouth to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 12 December 2025.

Sun 25/109:30SOU - ORD
1 stop15h 45mAer Lingus
Sun 1/221:00ORD - SOU
1 stop12h 35mAer Lingus
Deal found 11/12£606
Sun 25/117:45SOU - ORD
2 stops30h 10mVirgin Atlantic
Sun 1/218:45ORD - SOU
2 stops32h 05mVirgin Atlantic
Deal found 11/12£612
Sun 25/117:45SOU - ORD
1 stop26h 35mDelta
Sun 1/205:30ORD - SOU
2 stops21h 20mDelta
Deal found 11/12£631
Sun 25/117:45SOU - ORD
1 stop26h 35mKLM
Sun 1/217:25ORD - SOU
2 stops17h 40mKLM
Deal found 11/12£631
Sun 25/115:25SOU - ORD
3 stops34h 30mMultiple Airlines
Sun 1/218:30ORD - SOU
2 stops17h 00mMultiple Airlines
Deal found 11/12£699
Fri 13/220:10SOU - ORD
1 stop29h 05mBritish Airways
Sun 15/221:00ORD - SOU
1 stop12h 35mBritish Airways
Deal found 9/12£760
Sun 25/117:45SOU - MDW
2 stops29h 44mKLM
Sun 1/210:48MDW - SOU
2 stops16h 02mKLM
Deal found 11/12£636
Wed 13/509:05SOU - ORD
2 stops18h 47mDelta
Sun 17/516:20ORD - SOU
1 stop10h 15mDelta
Deal found 10/12£646

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 12 December 2025.

Round-trip from

£606

One-way from

£329

Popular in

July

Cheapest in

February

Average price

£591
Aer Lingus
  • Aer Lingus
  • 25/1-1/2
  • 2 total stops
  • 28h 20m total
  • Portsmouth to Chicago
Search Deals
18/3
  • 18/3
  • 3 total stops
  • 37h 55m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£61 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 December 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 12 December 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

Sun 25/1

09:30-19:15

1 stop15h 45m

Chicago O'Hare Intl

Sun 1/2

21:00-15:35

1 stop12h 35m

£606

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 25/1

17:45-17:55

2 stops30h 10m

Chicago O'Hare Intl

Sun 1/2

18:45-08:50

2 stops32h 05m

£612

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 25/1

17:45-14:20

1 stop26h 35m

Chicago O'Hare Intl

Sun 1/2

05:30-08:50

2 stops21h 20m

£631

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 25/1

17:45-14:20

1 stop26h 35m

Chicago O'Hare Intl

Sun 1/2

17:25-17:05

2 stops17h 40m

£631

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 25/1

17:45-17:29

2 stops29h 44m

Chicago Midway

Sun 1/2

10:48-08:50

2 stops16h 02m

£636

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 13/5

09:05-21:52

2 stops18h 47m

Chicago O'Hare Intl

Sun 17/5

16:20-08:35

1 stop10h 15m

£646

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 25/1

15:25-19:55

3 stops34h 30m

Chicago O'Hare Intl

Sun 1/2

18:30-17:30

2 stops17h 00m

£699

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 13/2

20:10-19:15

1 stop29h 05m

Chicago O'Hare Intl

Sun 15/2

21:00-15:35

1 stop12h 35m

£760

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 18/3

09:25-18:20

3 stops37h 55m

£329

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Mon 23/3

17:45-18:20

3 stops29h 35m

£340

Flights are sorted by cheapest return flights first.

Deals found on 11/12

Showing 1-10 of 15 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, December is the cheapest month in which you can book a flight from Portsmouth to Chicago (average of £237). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £500). 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 12 December 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 12 December 2025.

The most flights from P0R to CHI are scheduled on a Wednesday (48 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (34 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 £606, Aer Lingus can have you in Chicago from Portsmouth in 15h 45m. 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 Austrian Airlines (88%), Brussels Airlines (88%) or Lufthansa (88%) 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 £1,122 for a flight from Portsmouth to Chicago. The cheapest flight overall is £352 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £627.

  • 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, December is the cheapest month in which you can book a flight from Portsmouth to Chicago (average of £237). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £500). 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest£315Average£488FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Virgin AtlanticCheapest£346Average£528FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
Scandinavian AirlinesCheapest£360Average£478FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
Aer LingusCheapest£366Average£622FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
TAP AIR PORTUGALCheapest£369Average£608FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Brussels AirlinesCheapest£387Average£544FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
LufthansaCheapest£396Average£570FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
British AirwaysCheapest£404Average£566FlexibilityNo cancel feeOn-time70%
Search British Airways flights
Austrian AirlinesCheapest£405Average£609FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
United AirlinesCheapest£410Average£552FlexibilityNo 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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