HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portsmouth

$501+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LHR
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
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

Keep the following information in mind while searching for Chicago to Portsmouth flight deals. Data was last updated August 17, 2025.

Round-trip from

$849
(Mytrip)

One-way from

$501
(KLM)

Popular in

June

Cheapest in

February

Average price

$713
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 ($203 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 August 2025
Search Deals

Find 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 August 17, 2025.

This Mytrip deal was found by Cheapflights users on 8/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/293:45 pmORD - SOU
1 stop10h 30mAer Lingus
Mon 10/69:40 amSOU - ORD
1 stop15h 20mAer Lingus
Deal found 8/15$849
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/299:15 pmORD - SOU
1 stop28h 50mMultiple Airlines
Tue 10/148:00 pmSOU - ORD
2 stops46h 35mMultiple Airlines
Deal found 8/16$892
This Gotogate deal was found by Cheapflights users on 8/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:40 pmORD - SOU
1 stop10h 05mVirgin Atlantic
Tue 10/149:20 amSOU - ORD
1 stop10h 50mVirgin Atlantic
Deal found 8/16$900
This Rumbo deal was found by Cheapflights users on 8/16. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:30 pmMDW - SOU
2 stops32h 15mVirgin Atlantic
Tue 10/145:35 pmSOU - MDW
2 stops30h 50mVirgin Atlantic
Deal found 8/16$904
This KLM deal was found by Cheapflights users on 8/14. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/14:40 pmORD - SOU
1 stop18h 20mKLM
Tue 10/75:35 pmSOU - ORD
1 stop27h 05mKLM
Deal found 8/14$922
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 10/124:15 pmORD - SOU
1 stop10h 30mDelta
Tue 10/219:20 amSOU - ORD
1 stop10h 50mDelta
Deal found 8/15$924
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 10/123:50 pmORD - SOU
2 stops19h 10mDelta
Mon 10/205:35 pmSOU - ORD
1 stop26h 35mDelta
Deal found 8/15$928
This KLM deal was found by Cheapflights users on 8/16. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2911:20 amORD - SOU
2 stops15h 25mKLM
Tue 10/149:20 amSOU - ORD
2 stops17h 59mKLM
Deal found 8/16$931
This Delta deal was found by Cheapflights users on 8/15. 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.
Mon 11/34:25 pmORD - SOU
1 stop18h 35mDelta
Mon 11/176:05 pmSOU - ORD
2 stops29h 31mDelta
Deal found 8/15$934
This KLM deal was found by Cheapflights users on 8/17. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:00 pmORD - SOU
2 stops13h 45mKLM
Wed 10/89:20 amSOU - ORD
2 stops17h 59mKLM
Deal found 8/17$938
This Mytrip deal was found by Cheapflights users on 8/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:30 amORD - SOU
3 stops19h 45mMultiple Airlines
Mon 10/68:05 amSOU - ORD
3 stops40h 19mMultiple Airlines
Deal found 8/15$972
This Delta deal was found by Cheapflights users on 8/15. 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 12/239:30 amMDW - SOU
2 stops16h 40mDelta
Wed 12/315:30 pmSOU - MDW
2 stops34h 35mDelta
Deal found 8/15$1,163

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 August 17, 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

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 9/29

3:45 pm-8:15 am

1 stop10h 30m

Southampton Eastleigh

Mon 10/6

9:40 am-7:00 pm

1 stop15h 20m

$849

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 9/29

9:15 pm-8:05 am

1 stop28h 50m

Southampton Eastleigh

Tue 10/14

8:00 pm-12:35 pm

2 stops46h 35m

$892

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 9/29

4:40 pm-8:45 am

1 stop10h 05m

Southampton Eastleigh

Tue 10/14

9:20 am-2:10 pm

1 stop10h 50m

$900

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Mon 9/29

6:30 pm-8:45 am

2 stops32h 15m

Southampton Eastleigh

Tue 10/14

5:35 pm-6:25 pm

2 stops30h 50m

$904

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Wed 10/1

4:40 pm-5:00 pm

1 stop18h 20m

Southampton Eastleigh

Tue 10/7

5:35 pm-2:40 pm

1 stop27h 05m

$922

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 11/3

4:25 pm-5:00 pm

1 stop18h 35m

Southampton Eastleigh

Wed 11/19

8:40 am-2:20 pm

1 stop11h 40m

$924

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sun 11/9

4:25 pm-5:25 pm

1 stop19h 00m

Southampton Eastleigh

Wed 11/19

8:40 am-2:20 pm

1 stop11h 40m

$924

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 10/13

4:40 pm-8:45 am

1 stop10h 05m

Southampton Eastleigh

Mon 10/20

5:35 pm-2:10 pm

1 stop26h 35m

$924

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 11/3

4:25 pm-5:00 pm

1 stop18h 35m

Southampton Eastleigh

Fri 11/21

8:40 am-2:20 pm

1 stop11h 40m

$924

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Wed 10/15

4:40 pm-8:45 am

1 stop10h 05m

Southampton Eastleigh

Mon 10/20

5:35 pm-2:10 pm

1 stop26h 35m

$924

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 33 results
1
2
3
4

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, November is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $661). Flying from Chicago to Portsmouth in June is currently the most expensive (average of $1,097). 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 August 17, 2025.

When flying from Chicago to Portsmouth, 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 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 September 22, 2024.

Travelers seeking maximum savings on their Chicago to Portsmouth flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Thursday afternoons 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 August 17, 2025.

The most flights from CHI to P0R are scheduled on a Friday (57 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (45 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 August 17, 2025.
Peruse reviews from past customers who have flown with Delta and KLM 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
8.0
Very good
7,986 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
7,986 reviews
Delta
8.0
Very good
7,986 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
1,385 reviews
Delta
8.0
Very good
7,986 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Entertainment

7.9

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 Chicago to Portsmouth. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Portsmouth one-way?

    $501 is the cheapest one-way deal found within the past few days, from KLM. You may also be able to find cheap deals on Delta and Aer Lingus, with prices starting from $514 and $524, respectively.

  • 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 (63%), Austrian Airlines (63%) or United Airlines (63%) 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 $342. On average you can expect to pay $2,465. The most popular route, (Chicago O'Hare Intl - Southampton Eastleigh), can usually be booked for $849.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $661). Flying from Chicago to Portsmouth in June is currently the most expensive (average of $1,097). 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
Midway to Heathrow flights
O'Hare Intl to Edinburgh flights
O'Hare Intl to Stansted flights
O'Hare Intl to Luton flights
St. Louis to Heathrow flights
St. Louis to Gatwick flights
St. Louis to London City flights
O'Hare Intl to Manchester flights
Midway to Edinburgh flights
Midway to Gatwick flights
St. Louis to Edinburgh flights
Midway to Manchester flights
O'Hare Intl to Southampton flights
O'Hare Intl to Leeds flights
O'Hare Intl to Liverpool flights
O'Hare Intl to Birmingham flights
St. Louis to Manchester flights
Peoria to Heathrow flights
O'Hare Intl to Newcastle upon Tyne flights
Midway to London City flights
St. Louis to Luton flights
Midway to Southampton flights
St. Louis to Stansted flights
O'Hare Intl to Bristol flights
Moline to Heathrow flights
Midway to Leeds flights
Evansville to Heathrow flights
Midway to Newcastle upon Tyne flights
Midway to Birmingham flights
Springfield to Heathrow flights
Midway to Bristol flights
St. Louis to Birmingham flights
Bloomington to Heathrow flights
O'Hare Intl to Darlington flights
Champaign to Heathrow flights
O'Hare Intl to Grimsby flights
O'Hare Intl to Newquay flights
Evansville to Leeds flights
Midway to Grimsby flights
Bloomington to Gatwick flights
Dubuque to Heathrow flights
Evansville to Gatwick flights
Evansville to Manchester flights
St. Louis to Leeds flights
Midway to Luton 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 August 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$51Average$632FlexibilityNo cancel feeOn-time62%
SWISSCheapest$257Average$723FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$338Average$591FlexibilityNo cancel feeOn-time77%
DeltaCheapest$345Average$909FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$400Average$917FlexibilityNo cancel feeOn-time76%
IcelandairCheapest$469Average$654FlexibilityNo cancel feeOn-time76%
British AirwaysCheapest$502Average$793FlexibilityNo cancel feeOn-time70%
TAP AIR PORTUGALCheapest$508Average$797FlexibilityNo cancel feeOn-timeN/A
Aer LingusCheapest$553Average$936FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$568Average$760FlexibilityNo 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.