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Cheap flights from Portsmouth to Chicago from £585

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
18 Jun — 25 Jun1
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 13 June 2025.

Round-trip from

£585

Popular in

August

Cheapest in

February

Average price

£530
KLM
  • KLM
  • 8/7-15/7
  • 2 total stops
  • 45h 45m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£55 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 June 2025
Search Deals

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 13 June 2025.

Tue 8/718:25SOU - ORD
1 stop26h 15mKLM
Tue 15/716:20ORD - SOU
1 stop19h 30mKLM
Deal found 11/6£585
Tue 8/709:20SOU - ORD
2 stops18h 23mDelta
Tue 15/710:20ORD - SOU
2 stops16h 25mDelta
Deal found 11/6£747
Sun 27/709:10SOU - ORD
2 stops33h 20mMultiple Airlines
Sun 3/814:00ORD - SOU
2 stops23h 30mMultiple Airlines
Deal found 12/6£780
Sun 27/709:20SOU - MDW
2 stops15h 20mKLM
Sun 3/819:21MDW - SOU
2 stops16h 29mKLM
Deal found 12/6£1,296
Sun 27/709:20SOU - MDW
2 stops15h 20mDelta
Sun 3/819:21MDW - SOU
2 stops16h 29mDelta
Deal found 12/6£1,917

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 13 June 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 8/7

18:25-14:40

1 stop26h 15m

Chicago O'Hare Intl

Tue 15/7

16:20-17:50

1 stop19h 30m

£585

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 8/7

09:20-21:43

2 stops18h 23m

Chicago O'Hare Intl

Tue 15/7

10:20-08:45

2 stops16h 25m

£747

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 27/7

09:10-12:30

2 stops33h 20m

Chicago O'Hare Intl

Sun 3/8

14:00-19:30

2 stops23h 30m

£780

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 27/7

09:20-18:40

2 stops15h 20m

Chicago Midway

Sun 3/8

19:21-17:50

2 stops16h 29m

£1,296

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 27/7

09:20-18:40

2 stops15h 20m

Chicago Midway

Sun 3/8

19:21-17:50

2 stops16h 29m

£1,917

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 3/8

17:35-14:10

1 stop26h 35m

£1,478

Flights are sorted by cheapest return flights first.

Deals found on 11/6

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 13 June 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 13 June 2025.

The most flights from P0R to CHI are scheduled on a Monday (53 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (48 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 13 June 2025.
Read reviews from past customers who have flown Delta and KLM from Portsmouth to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
Delta
8.0
Very Good
7,950 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very Good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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 (92%), Austrian Airlines (92%) or United Airlines (92%) 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 £1,784 for a flight from Portsmouth to Chicago. The cheapest flight overall is £373 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £562.

  • 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 13 June 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest£310Average£484FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Scandinavian AirlinesCheapest£350Average£496FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£363Average£599FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Virgin AtlanticCheapest£381Average£578FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
Brussels AirlinesCheapest£389Average£629FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
Austrian AirlinesCheapest£397Average£560FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
LufthansaCheapest£397Average£569FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
United AirlinesCheapest£398Average£566FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest£400Average£620FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
British AirwaysCheapest£404Average£563FlexibilityNo cancel feeOn-time70%
Search British Airways flights

Fly with Cheapflights

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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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