HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portsmouth

$317+ Cheap flights from Chicago (CHI) to Portsmouth, England

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LHR
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Portsmouth with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Portsmouth

Cheapest flights from Chicago to Portsmouth
Explore the most affordable flight options available from Chicago to Portsmouth. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This Delta deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:25 pmORD - SOU
1 stop19h 00mDelta
Tue 1/65:35 pmSOU - ORD
1 stop26h 45mDelta
Deal found 12/12$861
This Delta deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 amORD - SOU
2 stops28h 00mDelta
Tue 1/65:35 pmSOU - ORD
1 stop26h 45mDelta
Deal found 12/12$967
This Delta deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:25 pmORD - SOU
1 stop9h 55mDelta
Wed 1/79:25 amSOU - ORD
1 stop10h 55mDelta
Deal found 12/13$1,219
This Delta deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:25 pmORD - SOU
1 stop9h 55mDelta
Mon 1/59:25 amSOU - ORD
1 stop10h 55mDelta
Deal found 12/12$1,248
This Delta deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:45 amORD - SOU
2 stops19h 25mDelta
Mon 1/59:25 amSOU - ORD
1 stop10h 55mDelta
Deal found 12/13$1,355

Find flight deals from Chicago to Portsmouth

Keep the following information in mind while searching for Chicago to Portsmouth flight deals. Data was last updated December 15, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$772
(KLM)

One-way from

$317
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$833
Provider with most accurate pricing for Chicago (CHI)-London (LON) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-London (LON) flights.
Search Deals
From Chicago (CHI) to Portsmouth
Search Deals
One-way flight from Chicago (CHI) to Portsmouth
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($204 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Portsmouth 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 2,558,603 searches. Data last updated December 15, 2025.
Use the filters below to find and compare flights from Chicago to Portsmouth that are best for you.

Fly from

Chicago

Fly to

Portsmouth

Route

Depart

Return

Price

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 1/27

1:29 pm-8:50 am

2 stops13h 21m

Southampton Eastleigh

Tue 2/3

9:25 am-5:55 pm

2 stops14h 30m

$782

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Tue 1/27

10:29 am-8:50 am

2 stops16h 21m

Southampton Eastleigh

Tue 2/3

9:25 am-11:56 pm

2 stops20h 31m

$782

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Thu 3/12

1:37 pm-8:05 am

2 stops13h 28m

Southampton Eastleigh

Fri 3/20

8:40 am-3:20 pm

1 stop11h 40m

$822

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sun 2/15

12:27 pm-5:05 pm

2 stops22h 38m

Southampton Eastleigh

Sun 2/22

5:45 pm-2:20 pm

1 stop26h 35m

$822

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 2/16

7:00 am-8:50 am

2 stops19h 50m

Southampton Eastleigh

Sun 2/22

5:45 pm-2:20 pm

1 stop26h 35m

$822

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Thu 3/12

1:37 pm-8:05 am

2 stops13h 28m

Southampton Eastleigh

Wed 3/18

8:40 am-3:20 pm

1 stop11h 40m

$831

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Thu 3/12

10:40 am-8:05 am

2 stops16h 25m

Southampton Eastleigh

Tue 3/17

5:35 pm-3:20 pm

1 stop26h 45m

$831

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sat 3/14

5:29 pm-8:20 am

2 stops33h 51m

Southampton Eastleigh

Sun 3/22

5:45 pm-3:20 pm

1 stop26h 35m

$833

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sat 2/14

5:37 pm-8:50 am

2 stops33h 13m

Southampton Eastleigh

Sun 2/22

5:45 pm-2:20 pm

1 stop26h 35m

$833

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sat 3/14

5:29 pm-8:20 am

2 stops33h 51m

Southampton Eastleigh

Sat 3/21

9:25 am-10:01 pm

2 stops41h 36m

$838

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chicago to Portsmouth

Have a flexible travel schedule? Discover the best time to fly to Portsmouth from Chicago with our price prediction graph.
Estimated round-trip 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 Chicago to Portsmouth

What is the cheapest month to book a flight from Chicago to Portsmouth?

Currently, June is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $375). Flying from Chicago to Portsmouth in July is currently the most expensive (average of $604). 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 CHI to P0R?

Find hourly flight availability from Chicago to Portsmouth. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

When flying from Chicago to Portsmouth, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 33% versus a flight at noon.

What is the cheapest day to fly from Chicago to Portsmouth?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Portsmouth. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Portsmouth flight should consider departing on Sunday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Portsmouth

Explore weekly flight availability from Chicago to Portsmouth. 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 December 15, 2025.

The most flights from CHI to P0R are scheduled on a Monday (45 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (26 on average).

Reviews of airlines servicing Portsmouth

Get insights into the airlines that provide service to Portsmouth. 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 Portsmouth. Reviews last updated December 15, 2025.
Peruse reviews from past customers who have flown with Delta, KLM, and Aer Lingus from Chicago to Portsmouth 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.
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
KLM
7.7
Good
1,430 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Aer Lingus
7.2
Good
1,394 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Portsmouth. 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 Chicago to Portsmouth?

    A quick flight from Chicago to Portsmouth can take about 13h 21m. KLM provides one of the quickest options available for as low as $782. The distance from Chicago to Portsmouth is about 3924 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Portsmouth consider choosing Air Canada (64%), Austrian Airlines (64%) or United Airlines (64%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Portsmouth?

    The cheapest flight price from Chicago to Portsmouth is $357. On average you can expect to pay $2,578. The most popular route, (Chicago O'Hare Intl - Southampton Eastleigh), can usually be booked for $782.

  • Can I find deals for flights from Chicago to Portsmouth that include hotel bookings?

    Yes. In addition to deals on Chicago to Portsmouth flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portsmouth?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portsmouth.

  • Can I find deals for business class flights from Chicago to Portsmouth?

    Yes. Cheapflights offers flight deals from Chicago to Portsmouth 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 Chicago to Portsmouth?

    Currently, June is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $375). Flying from Chicago to Portsmouth in July is currently the most expensive (average of $604). 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 Chicago to Portsmouth

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Heathrow flights
O'Hare Intl to Gatwick flights
O'Hare Intl to London City flights
O'Hare Intl to Stansted flights
Midway to Heathrow flights
O'Hare Intl to Luton flights
O'Hare Intl to Edinburgh flights
St. Louis to Heathrow flights
O'Hare Intl to Manchester flights
St. Louis to Gatwick flights
Midway to Edinburgh flights
Midway to Manchester flights
St. Louis to London City flights
Midway to Gatwick flights
St. Louis to Edinburgh flights
St. Louis to Stansted flights
O'Hare Intl to Southampton flights
O'Hare Intl to Leeds flights
O'Hare Intl to Birmingham flights
Midway to London City flights
Moline to Heathrow flights
St. Louis to Manchester flights
Peoria to Heathrow flights
O'Hare Intl to Liverpool flights
O'Hare Intl to Bristol flights
O'Hare Intl to Newcastle upon Tyne flights
Midway to Stansted flights
Midway to Birmingham flights
St. Louis to Luton flights
Midway to Bristol flights
Peoria to London City flights
Springfield to Heathrow flights
Bloomington to Heathrow flights
O'Hare Intl to Exeter flights
Moline to Gatwick flights
Midway to Newcastle upon Tyne flights
St. Louis to Birmingham flights
O'Hare Intl to Newquay flights
Evansville to Leeds flights
Evansville to Heathrow flights
Champaign to Heathrow flights
Peoria to Gatwick flights
Midway to Leeds flights
St. Louis to Leeds flights
Bloomington to Gatwick flights
O'Hare Intl to Grimsby flights
Dubuque to Heathrow flights
Evansville to Gatwick flights

Top 10 airlines flying from Chicago to Portsmouth

Discover the top 10 airlines that operate flights from Chicago to Portsmouth. 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 2,558,603 searches. Data last updated December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$51Average$632FlexibilityNo cancel feeOn-time62%
SWISSCheapest$257Average$668FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$338Average$585FlexibilityNo cancel feeOn-time77%
DeltaCheapest$345Average$927FlexibilityNo cancel feeOn-timeN/A
TAP AIR PORTUGALCheapest$428Average$616FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$460Average$965FlexibilityNo cancel feeOn-time76%
IcelandairCheapest$481Average$655FlexibilityNo cancel feeOn-time76%
British AirwaysCheapest$502Average$795FlexibilityNo cancel feeOn-time70%
Aer LingusCheapest$504Average$969FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$518Average$771FlexibilityNo cancel feeOn-time76%

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.