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Cheap flights from Portsmouth to Chicago from £453

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 30/9. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
19 Aug — 26 Aug1
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 20 July 2026.

Sun 6/917:20
SOU
-
ORD
1 stop27h 10m
Delta
Sun 13/916:20
ORD
-
SOU
1 stop10h 15m
Delta
Deal found 15/7£740
Sun 6/917:20
SOU
-
ORD
1 stop27h 10m
Delta
Sat 12/918:24
ORD
-
SOU
2 stops32h 11m
Delta
Deal found 15/7£743
Sun 11/1017:20
SOU
-
ORD
1 stop27h 10m
Delta
Mon 19/1009:59
ORD
-
SOU
2 stops16h 36m
Delta
Deal found 19/7£769
Sat 5/909:15
SOU
-
ORD
1 stop11h 00m
Delta
Sun 13/916:20
ORD
-
SOU
1 stop10h 15m
Delta
Deal found 15/7£769
Sat 5/917:20
SOU
-
MDW
2 stops35h 16m
Delta
Sat 12/917:45
MDW
-
SOU
2 stops17h 05m
Delta
Deal found 15/7£773
Sat 5/917:20
SOU
-
ORD
2 stops29h 31m
Delta
Sat 12/918:24
ORD
-
SOU
2 stops32h 11m
Delta
Deal found 15/7£773
Sat 10/1009:20
SOU
-
ORD
1 stop10h 55m
Delta
Tue 20/1016:20
ORD
-
SOU
1 stop10h 25m
Delta
Deal found 19/7£798
Wed 12/817:20
SOU
-
ORD
1 stop26h 40m
Aer Lingus
Wed 19/815:45
ORD
-
SOU
1 stop19h 05m
Aer Lingus
Deal found 15/7£801
Sat 22/809:20
SOU
-
ORD
1 stop15h 55m
Aer Lingus
Sat 29/815:45
ORD
-
SOU
1 stop10h 50m
Aer Lingus
Deal found 18/7£805
Sat 15/817:20
SOU
-
ORD
1 stop26h 40m
Aer Lingus
Sat 22/821:00
ORD
-
SOU
1 stop16h 30m
Aer Lingus
Deal found 18/7£823
Sat 10/1009:20
SOU
-
ORD
1 stop10h 55m
Delta
Fri 23/1016:20
ORD
-
SOU
1 stop10h 25m
Delta
Deal found 19/7£828
Sun 11/1017:20
SOU
-
ORD
1 stop27h 10m
Delta
Sat 24/1016:20
ORD
-
SOU
1 stop11h 35m
Delta
Deal found 19/7£858

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 20 July 2026.

Round-trip from

£740

One-way from

£453

Popular in

July

Cheapest in

February

Average price

£715
Delta
  • Delta
  • 6/9-13/9
  • 2 total stops
  • 37h 25m total
  • Portsmouth to Chicago
Search Deals
British Airways
  • British Airways
  • 30/9
  • 1 total stop
  • 15h 55m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (£81 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 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 20 July 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

Sun 6/9

17:20-14:30

1 stop27h 10m

Chicago O'Hare Intl

Sun 13/9

16:20-08:35

1 stop10h 15m

£740

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 6/9

17:20-14:30

1 stop27h 10m

Chicago O'Hare Intl

Sat 12/9

18:24-08:35

2 stops32h 11m

£743

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Mon 12/10

17:20-14:15

1 stop26h 55m

Chicago O'Hare Intl

Mon 19/10

10:30-08:35

2 stops16h 05m

£769

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sun 11/10

17:20-14:30

1 stop27h 10m

Chicago O'Hare Intl

Thu 22/10

16:20-08:35

1 stop10h 15m

£769

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sat 5/9

17:20-14:15

1 stop26h 55m

Chicago O'Hare Intl

Sat 12/9

16:20-08:45

1 stop10h 25m

£769

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sun 6/9

09:15-22:36

2 stops19h 21m

Chicago Midway

Sat 12/9

17:45-16:50

2 stops17h 05m

£773

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Sat 5/9

17:20-22:36

2 stops35h 16m

Chicago Midway

Sat 12/9

17:45-16:50

2 stops17h 05m

£773
Fastest return journey

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Sat 10/10

09:20-14:15

1 stop10h 55m

Chicago O'Hare Intl

Tue 20/10

16:20-08:45

1 stop10h 25m

£798

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Tue 13/10

09:05-14:15

1 stop11h 10m

Chicago O'Hare Intl

Sat 24/10

16:20-09:55

1 stop11h 35m

£858

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Mon 12/10

09:20-19:15

1 stop15h 55m

Chicago O'Hare Intl

Sun 25/10

16:55-08:40

1 stop10h 45m

£922

Flights are sorted by cheapest return flights first.

Deals found on 16/7

Showing 1-10 of 35 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 20 July 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 20 July 2026.

The most flights from P0R to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (52 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 £1,002, Delta can have you in Chicago from Portsmouth in 19h 21m. The distance from Portsmouth to Chicago is about 3924 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 (90%), Austrian Airlines (90%) or United 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 £1,636 for a flight from Portsmouth to Chicago. The cheapest flight overall is £379 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £769.

  • 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portsmouth to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Heathrow to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Stansted to O'Hare Intl flights
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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
Manchester to St. Louis flights
London City to St. Louis flights
Birmingham to O'Hare Intl flights
Edinburgh to Midway flights
Gatwick to Midway flights
Birmingham to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
London City to Midway flights
Edinburgh to St. Louis flights
Liverpool to O'Hare Intl flights
Leeds to O'Hare Intl flights
Newcastle upon Tyne to Midway flights
Bristol to O'Hare Intl flights
Southampton to O'Hare Intl flights
Luton to St. Louis flights
Bristol to Midway flights
Leeds to St. Louis flights
Grimsby to St. Louis flights
Birmingham to St. Louis flights
Heathrow to Moline flights
Exeter to O'Hare Intl flights
Heathrow to Peoria flights
Manchester to Moline flights
Southampton to Midway flights
Leeds to Midway flights
Manchester to Peoria flights
Darlington to Midway flights
Newcastle upon Tyne to St. Louis flights
Grimsby to O'Hare Intl flights
Newquay to O'Hare Intl flights
Edinburgh to Moline flights
Doncaster to O'Hare Intl flights
Darlington to O'Hare Intl flights
Heathrow to Springfield flights
Gatwick to Evansville flights
London City to Evansville flights
Heathrow to Dubuque flights
Heathrow to Evansville 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 20 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£302Average£596FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
IcelandairCheapest£348Average£491FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Aer LingusCheapest£363Average£667FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
Scandinavian AirlinesCheapest£375Average£525FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
TAP AIR PORTUGALCheapest£386Average£548FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Brussels AirlinesCheapest£394Average£614FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
British AirwaysCheapest£412Average£656FlexibilityNo cancel feeOn-time70%
Search British Airways flights
LufthansaCheapest£420Average£631FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
United AirlinesCheapest£429Average£658FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
FinnairCheapest£430Average£692FlexibilityNo cancel feeOn-time76%
Search Finnair 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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