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Cheap flights from Portsmouth to Chicago from £416

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 31/5. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
20 Jun — 27 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap 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 21 May 2026.

Tue 9/617:20
SOU
-
ORD
3 stops34h 05m
Multiple Airlines
Mon 15/622:25
ORD
-
SOU
3 stops28h 10m
Multiple Airlines
Deal found 18/5£778
Tue 15/919:55
SOU
-
ORD
2 stops23h 55m
British Airways
Sun 27/915:45
ORD
-
SOU
1 stop19h 05m
British Airways
Deal found 18/5£798
Mon 6/718:05
SOU
-
ORD
1 stop26h 10m
KLM
Mon 13/711:30
ORD
-
SOU
2 stops15h 15m
KLM
Deal found 20/5£798
Tue 9/617:20
SOU
-
ORD
1 stop27h 10m
KLM
Mon 15/616:50
ORD
-
SOU
1 stop18h 00m
KLM
Deal found 18/5£810
Wed 3/620:00
SOU
-
ORD
1 stop21h 29m
Multiple Airlines
Mon 15/621:00
ORD
-
SOU
1 stop13h 50m
Multiple Airlines
Deal found 17/5£812
Wed 3/609:05
SOU
-
ORD
1 stop11h 25m
KLM
Mon 15/611:30
ORD
-
SOU
2 stops15h 05m
KLM
Deal found 17/5£813
Mon 6/718:05
SOU
-
MDW
2 stops28h 10m
Delta
Mon 13/713:18
MDW
-
SOU
2 stops13h 27m
Delta
Deal found 20/5£831
Fri 5/609:05
SOU
-
MDW
2 stops18h 04m
KLM
Thu 11/611:05
MDW
-
SOU
2 stops15h 30m
KLM
Deal found 19/5£854
Wed 3/609:05
SOU
-
MDW
2 stops14h 51m
Delta
Mon 15/609:54
MDW
-
SOU
2 stops16h 41m
Delta
Deal found 17/5£859
Fri 5/609:05
SOU
-
MDW
2 stops18h 04m
Delta
Thu 11/609:17
MDW
-
SOU
2 stops17h 18m
Delta
Deal found 17/5£868
Sat 4/717:30
SOU
-
MDW
2 stops30h 48m
Virgin Atlantic
Sat 11/718:55
MDW
-
SOU
2 stops31h 50m
Virgin Atlantic
Deal found 20/5£1,627

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 21 May 2026.

Round-trip from

£778

One-way from

£416

Popular in

July

Cheapest in

February

Average price

£582
9/6-15/6
  • 9/6-15/6
  • 6 total stops
  • 62h 15m total
  • Portsmouth to Chicago
Search Deals
31/5
  • 31/5
  • 3 total stops
  • 54h 40m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£51 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 May 2026
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 21 May 2026.
Use the filters below to find and compare flights from Portsmouth to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 15/9

19:55-13:50

2 stops23h 55m

Chicago O'Hare Intl

Sun 27/9

15:45-16:50

1 stop19h 05m

£798

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 3/6

15:35-13:10

3 stops27h 35m

Chicago O'Hare Intl

Mon 15/6

15:40-19:30

3 stops21h 50m

£812

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Wed 3/6

09:05-20:14

2 stops17h 09m

Chicago O'Hare Intl

Mon 15/6

11:30-08:35

2 stops15h 05m

£819

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 9/6

18:10-22:05

3 stops33h 55m

Chicago O'Hare Intl

Mon 15/6

09:55-16:50

2 stops24h 55m

£829

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Mon 6/7

18:05-16:15

2 stops28h 10m

Chicago Midway

Mon 13/7

13:18-08:45

2 stops13h 27m

£831

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 5/6

09:05-21:09

2 stops18h 04m

Chicago Midway

Thu 11/6

11:05-08:35

2 stops15h 30m

£854

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 5/6

09:05-21:20

2 stops18h 15m

Chicago O'Hare Intl

Thu 11/6

11:30-08:35

2 stops15h 05m

£854

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Wed 3/6

09:05-17:56

2 stops14h 51m

Chicago Midway

Mon 15/6

09:54-08:35

2 stops16h 41m

£859
Fastest return journey

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Fri 5/6

09:05-14:15

1 stop11h 10m

Chicago O'Hare Intl

Thu 11/6

11:23-08:35

2 stops15h 12m

£864

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 5/6

09:05-21:09

2 stops18h 04m

Chicago Midway

Thu 11/6

09:17-08:35

2 stops17h 18m

£868

Flights are sorted by cheapest return flights first.

Deals found on 19/5

Showing 1-10 of 27 resultsSorted by cheapest first
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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 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 21 May 2026.

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.

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 21 May 2026.

The most flights from P0R to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (33 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 £819, British Airways can have you in Chicago from Portsmouth in 17h 09m. 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 SriLankan Airlines (94%), Air Canada (90%) or Austrian Airlines (90%) 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 £1,201 for a flight from Portsmouth to Chicago. The cheapest flight overall is £454 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £772.

  • 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.

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.
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Heathrow to St. Louis flights
Manchester to O'Hare Intl flights
Manchester to Midway flights
Edinburgh to O'Hare Intl flights
Gatwick to St. Louis flights
Stansted to St. Louis flights
London City to St. Louis flights
Gatwick to Midway flights
Birmingham to O'Hare Intl flights
Edinburgh to Midway flights
Birmingham to Midway flights
Liverpool to O'Hare Intl flights
Leeds to O'Hare Intl flights
Luton to St. Louis flights
Southampton to O'Hare Intl flights
Norwich to O'Hare Intl flights
Manchester to St. Louis flights
Newcastle upon Tyne to O'Hare Intl flights
Southend to O'Hare Intl flights
Edinburgh to St. Louis flights
Bristol to O'Hare Intl flights
Leeds to Midway flights
Heathrow to Peoria flights
Bristol to Midway flights
Birmingham to St. Louis flights
Manchester to Peoria flights
Grimsby to O'Hare Intl flights
Exeter to O'Hare Intl flights
Heathrow to Moline flights
London City to Midway flights
Newquay to O'Hare Intl flights
Heathrow to Champaign flights
Heathrow to Springfield flights
Newcastle upon Tyne to Midway flights
London City to Peoria flights
Newcastle upon Tyne to St. Louis flights
Heathrow to Evansville flights
Darlington to Midway flights
Southampton to Midway flights
Edinburgh to Moline flights
Doncaster to O'Hare Intl flights
Darlington to O'Hare Intl flights
Gatwick to Champaign flights
Grimsby to St. Louis flights

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 21 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£345Average£582FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
IcelandairCheapest£349Average£507FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£364Average£650FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
Scandinavian AirlinesCheapest£370Average£520FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£386Average£515FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Brussels AirlinesCheapest£395Average£586FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
British AirwaysCheapest£396Average£619FlexibilityNo cancel feeOn-time70%
Search British Airways flights
LufthansaCheapest£396Average£616FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Austrian AirlinesCheapest£404Average£642FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
United AirlinesCheapest£416Average£629FlexibilityNo 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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