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Cheap flights from Portsmouth to Chicago from £560

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19/8. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
13 Jul — 20 Jul1
1 adult

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 8 July 2025.

Round-trip from

£560

Popular in

August

Cheapest in

February

Average price

£646
Delta
  • Delta
  • 19/8-8/9
  • 3 total stops
  • 50h 40m total
  • Portsmouth to Chicago
Highest demand for flights based on searches. 12% potential increase in price (£53 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (£10 potential savings vs. average return price).
Average for round-trip flights in July 2025

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 8 July 2025.

Tue 19/818:25SOU - ORD
1 stop26h 15mDelta
Mon 8/910:35ORD - SOU
2 stops24h 25mDelta
Deal found 6/7£560
Mon 18/809:20SOU - MDW
2 stops18h 24mDelta
Tue 9/913:08MDW - SOU
2 stops13h 37mDelta
Deal found 6/7£565
Thu 21/809:40SOU - ORD
1 stop15h 20mAer Lingus
Thu 28/815:45ORD - SOU
1 stop10h 55mAer Lingus
Deal found 7/7£701
Thu 21/809:40SOU - ORD
2 stops17h 35mMultiple Airlines
Thu 28/819:25ORD - SOU
2 stops18h 05mMultiple Airlines
Deal found 7/7£762

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 8 July 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

Tue 19/8

18:25-14:40

1 stop26h 15m

Chicago O'Hare Intl

Mon 8/9

10:35-17:00

2 stops24h 25m

£560

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 18/8

09:20-21:44

2 stops18h 24m

Chicago Midway

Tue 9/9

13:08-08:45

2 stops13h 37m

£565

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 21/8

09:40-19:00

1 stop15h 20m

Chicago O'Hare Intl

Thu 28/8

15:45-08:40

1 stop10h 55m

£701

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 21/8

09:40-21:15

2 stops17h 35m

Chicago O'Hare Intl

Thu 28/8

19:25-19:30

2 stops18h 05m

£762

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 22/8

09:20-14:10

1 stop10h 50m

£1,269

Flights are sorted by cheapest return flights first.

Deals found on 6/7

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 8 July 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 8 July 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).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 8 July 2025.
Check out reviews from past customers who have flown with Delta and Aer Lingus from Portsmouth to Chicago 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.

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very Good

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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

    Consider Air Canada (89%), Austrian Airlines (89%) or United Airlines (89%) 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 £1,822 for a flight from Portsmouth to Chicago. The cheapest flight overall is £401 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £706.

  • 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

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.

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 8 July 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest£309Average£484FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Scandinavian AirlinesCheapest£349Average£499FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£362Average£608FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Virgin AtlanticCheapest£380Average£576FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
Brussels AirlinesCheapest£389Average£599FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
LufthansaCheapest£393Average£571FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Austrian AirlinesCheapest£396Average£574FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
United AirlinesCheapest£398Average£566FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest£399Average£629FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
British AirwaysCheapest£401Average£562FlexibilityNo cancel feeOn-time70%
Search British Airways 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?

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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.

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