Find flights
When to book
FAQs

Cheap flights from Portsmouth to Chicago from £326

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 19/4. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — CHI
7 Mar — 14 Mar1
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 5 February 2026.

Thu 19/308:50
SOU
-
ORD
2 stops17h 59m
Delta
Thu 26/311:10
ORD
-
SOU
2 stops16h 10m
Delta
Deal found 2/2£675
Thu 19/318:05
SOU
-
ORD
1 stop26h 15m
KLM
Thu 26/310:40
ORD
-
SOU
2 stops16h 40m
KLM
Deal found 2/2£725
Thu 5/316:05
SOU
-
ORD
1 stop27h 55m
British Airways
Mon 9/316:50
ORD
-
SOU
1 stop14h 05m
British Airways
Deal found 2/2£733
Thu 19/318:05
SOU
-
ORD
3 stops27h 20m
Multiple Airlines
Thu 26/307:15
ORD
-
SOU
3 stops29h 15m
Multiple Airlines
Deal found 2/2£779
Fri 27/309:30
SOU
-
ORD
2 stops28h 09m
Aer Lingus
Mon 6/415:45
ORD
-
SOU
1 stop10h 55m
Aer Lingus
Deal found 4/2£786
Thu 19/308:50
SOU
-
MDW
2 stops18h 41m
Virgin Atlantic
Thu 26/312:47
MDW
-
SOU
2 stops23h 13m
Virgin Atlantic
Deal found 2/2£803
Fri 27/308:50
SOU
-
MDW
2 stops14h 50m
Virgin Atlantic
Sun 5/413:10
MDW
-
SOU
2 stops13h 25m
Virgin Atlantic
Deal found 3/2£1,263
Fri 27/308:50
SOU
-
MDW
2 stops14h 50m
Delta
Mon 6/413:10
MDW
-
SOU
2 stops13h 25m
Delta
Deal found 3/2£1,586
Fri 27/308:50
SOU
-
MDW
2 stops14h 50m
Delta
Sun 5/409:30
MDW
-
SOU
2 stops17h 05m
Delta
Deal found 4/2£1,587
Thu 26/308:50
SOU
-
MDW
2 stops14h 50m
KLM
Mon 6/419:20
MDW
-
SOU
2 stops15h 30m
KLM
Deal found 3/2£1,703
Thu 26/308:50
SOU
-
MDW
2 stops14h 50m
KLM
Sun 5/413:10
MDW
-
SOU
2 stops13h 25m
KLM
Deal found 3/2£1,733

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 5 February 2026.

Round-trip from

£675

One-way from

£326

Popular in

July

Cheapest in

February

Average price

£422
Delta
  • Delta
  • 19/3-26/3
  • 4 total stops
  • 34h 09m total
  • Portsmouth to Chicago
Search Deals
19/4
  • 19/4
  • 3 total stops
  • 58h 35m total
  • Portsmouth to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£63 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 February 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 5 February 2026.
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

Thu 19/3

08:50-21:49

2 stops17h 59m

Chicago O'Hare Intl

Thu 26/3

11:10-08:20

2 stops16h 10m

£675

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 19/3

18:05-15:20

1 stop26h 15m

Chicago O'Hare Intl

Thu 26/3

10:40-08:20

2 stops16h 40m

£725

SouthamptonChicago

SOU - ORD

SOUORD

Southampton Eastleigh

Thu 5/3

16:05-14:00

1 stop27h 55m

Chicago O'Hare Intl

Mon 9/3

16:50-11:55

1 stop14h 05m

£733

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 19/3

08:50-22:31

2 stops18h 41m

Chicago Midway

Thu 26/3

12:47-17:00

2 stops23h 13m

£803

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 27/3

08:50-18:40

2 stops14h 50m

Chicago Midway

Sun 5/4

13:10-08:35

2 stops13h 25m

£1,263

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 27/3

08:50-18:40

2 stops14h 50m

Chicago Midway

Mon 6/4

13:10-08:35

2 stops13h 25m

£1,586

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 27/3

08:50-18:40

2 stops14h 50m

Chicago Midway

Sun 5/4

09:30-08:35

2 stops17h 05m

£1,586

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 26/3

08:50-18:40

2 stops14h 50m

Chicago Midway

Mon 6/4

19:20-16:50

2 stops15h 30m

£1,703

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Fri 27/3

08:50-18:40

2 stops14h 50m

Chicago Midway

Mon 6/4

19:20-16:50

2 stops15h 30m

£1,703

SouthamptonChicago

SOU - MDW

SOUMDW

Southampton Eastleigh

Thu 26/3

08:50-18:40

2 stops14h 50m

Chicago Midway

Sun 5/4

13:10-08:35

2 stops13h 25m

£1,733

Flights are sorted by cheapest return flights first.

Deals found on 2/2

Showing 1-10 of 19 results
1
2

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 £214). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £492). 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 5 February 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 5 February 2026.

The most flights from P0R to CHI are scheduled on a Wednesday (38 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (22 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 £675, Delta can have you in Chicago from Portsmouth in 17h 59m. 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 SWISS (90%), Air Canada (89%) or Austrian 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 £1,264 for a flight from Portsmouth to Chicago. The cheapest flight overall is £362 while the most popular route, (Southampton Eastleigh - Chicago O'Hare Intl) is currently priced at £733.

  • 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 £214). Flying from Portsmouth to Chicago in July is currently the most expensive (average of £492). 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

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
Heathrow to Midway flights
Gatwick to O'Hare Intl flights
Stansted to O'Hare Intl flights
London City to O'Hare Intl flights
Luton to O'Hare Intl flights
Manchester to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Leeds to O'Hare Intl flights
Heathrow to St. Louis flights
Gatwick to Midway flights
Manchester to Midway flights
Edinburgh to Midway flights
Birmingham to O'Hare Intl flights
Gatwick to St. Louis flights
Birmingham to Midway flights
Newcastle upon Tyne to O'Hare Intl flights
London City to St. Louis flights
Heathrow to Evansville flights
Stansted to St. Louis flights
Liverpool to O'Hare Intl flights
Norwich to O'Hare Intl flights
Manchester to St. Louis flights
Newcastle upon Tyne to Midway flights
Heathrow to Moline flights
Grimsby to O'Hare Intl flights
Edinburgh to St. Louis flights
Heathrow to Champaign flights
Leeds to Midway flights
Southampton to O'Hare Intl flights
Gatwick to Champaign flights
Heathrow to Peoria flights
Exeter to O'Hare Intl flights
Luton to St. Louis flights
Bristol to O'Hare Intl flights
Bristol to Midway flights
London City to Midway flights
Manchester to Moline flights
London City to Peoria flights
Manchester to Peoria flights
Heathrow to Springfield flights
Birmingham to St. Louis flights
Southend to O'Hare Intl flights
Doncaster to O'Hare Intl flights
Darlington to O'Hare Intl flights
Edinburgh to Moline flights
Newcastle upon Tyne to St. Louis flights
Newquay to O'Hare Intl flights
Darlington to Midway flights
Leeds 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 5 February 2026.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest£332Average£475FlexibilityNo cancel feeOn-time76%
Search Icelandair flights
Virgin AtlanticCheapest£338Average£521FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights
Scandinavian AirlinesCheapest£353Average£473FlexibilityNo cancel feeOn-time77%
Search Scandinavian Airlines flights
Aer LingusCheapest£358Average£618FlexibilityNo cancel feeOn-timeN/A
Search Aer Lingus flights
TAP AIR PORTUGALCheapest£375Average£601FlexibilityNo cancel feeOn-timeN/A
Search TAP AIR PORTUGAL flights
Brussels AirlinesCheapest£378Average£532FlexibilityNo cancel feeOn-timeN/A
Search Brussels Airlines flights
LufthansaCheapest£387Average£563FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Austrian AirlinesCheapest£393Average£593FlexibilityNo cancel feeOn-time78%
Search Austrian Airlines flights
British AirwaysCheapest£394Average£570FlexibilityNo cancel feeOn-time70%
Search British Airways flights
United AirlinesCheapest£401Average£540FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.