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$828+ Cheap flights from Chicago (CHI) to Portsmouth, England

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LHR
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/264:50 pmORD - SOU
1 stop10h 55mMultiple Airlines
Wed 10/2912:25 pmSOU - ORD
2 stops35h 20mMultiple Airlines
Deal found 10/14$1,175
This KAYAK deal was found by Cheapflights users on 10/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:40 pmORD - SOU
1 stop10h 15mAer Lingus
Thu 11/139:30 amSOU - ORD
1 stop14h 25mAer Lingus
Deal found 10/14$1,359
This British Airways deal was found by Cheapflights users on 10/14. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1011:48 amORD - SOU
2 stops20h 17mBritish Airways
Thu 11/139:30 amSOU - ORD
1 stop14h 25mBritish Airways
Deal found 10/14$1,693
This British Airways deal was found by Cheapflights users on 10/13. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/293:50 pmORD - SOU
1 stop17h 45mBritish Airways
Sun 11/306:25 pmSOU - ORD
3 stops25h 25mBritish Airways
Deal found 10/13$1,734
This British Airways deal was found by Cheapflights users on 10/12. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/261:43 pmORD - SOU
2 stops22h 52mBritish Airways
Sun 11/29:30 amSOU - ORD
1 stop14h 25mBritish Airways
Deal found 10/12$1,754
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/265:25 pmORD - SOU
1 stop19h 00mDelta
Wed 10/298:40 amSOU - ORD
1 stop11h 40mDelta
Deal found 10/14$1,830
This Air France deal was found by Cheapflights users on 10/14. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/265:25 pmORD - SOU
1 stop19h 00mKLM
Wed 10/298:40 amSOU - ORD
1 stop11h 40mKLM
Deal found 10/14$1,831
This British Airways deal was found by Cheapflights users on 10/14. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:43 pmORD - SOU
2 stops19h 12mBritish Airways
Tue 11/412:25 pmSOU - ORD
1 stop11h 30mBritish Airways
Deal found 10/14$1,838

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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$828
(Delta)

Popular in

June

Cheapest in

February

Average price

$669
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
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 ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 14, 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

Wed 2/25

4:25 pm-8:20 am

1 stop9h 55m

Southampton Eastleigh

Sun 3/1

9:30 am-2:20 pm

1 stop10h 50m

$828

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Wed 2/25

9:20 am-8:20 am

2 stops17h 00m

Southampton Eastleigh

Sun 3/1

5:45 pm-6:08 pm

2 stops30h 23m

$843

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sun 10/26

7:30 pm-5:35 pm

2 stops17h 05m

Southampton Eastleigh

Wed 10/29

12:25 pm-11:05 am

2 stops27h 40m

$1,273

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Mon 11/10

11:48 am-2:05 pm

2 stops20h 17m

Southampton Eastleigh

Thu 11/13

9:30 am-5:55 pm

1 stop14h 25m

$1,693

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sat 11/29

3:50 pm-3:35 pm

1 stop17h 45m

Southampton Eastleigh

Sun 11/30

6:25 pm-1:50 pm

3 stops25h 25m

$1,734

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sun 10/26

1:43 pm-5:35 pm

2 stops22h 52m

Southampton Eastleigh

Sun 11/2

9:30 am-5:55 pm

1 stop14h 25m

$1,754

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sun 10/26

5:25 pm-5:25 pm

1 stop19h 00m

Southampton Eastleigh

Wed 10/29

8:40 am-3:20 pm

1 stop11h 40m

$1,830

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Sun 10/26

5:25 pm-5:25 pm

1 stop19h 00m

Southampton Eastleigh

Wed 10/29

8:40 am-3:20 pm

1 stop11h 40m

$1,831

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Thu 12/18

6:30 pm-8:50 am

2 stops32h 20m

$1,053

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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, May is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $391). Flying from Chicago to Portsmouth in July is currently the most expensive (average of $613). 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 October 14, 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 32% 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 Tuesday evenings when fares are most often at their lowest. Thursday mornings 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 October 14, 2025.

The most flights from CHI to P0R are scheduled on a Monday (57 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (51 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 October 14, 2025.
Peruse reviews from past customers who have flown with 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.
KLM
7.7
Good
1,402 reviews

Boarding

7.8

Comfort

7.6

Overall

7.7

Crew

8.4

Entertainment

7.1

Food

7.2

Reviews

1 / 20
2.0
Mediocre

Abisola,Oct 2025

LOS - CDG

The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
KLM
7.7
Good
1,402 reviews
KLM
7.7
Good
1,402 reviews

Boarding

7.8

Comfort

7.6

Overall

7.7

Crew

8.4

Entertainment

7.1

Food

7.2

Reviews

1 / 20
2.0
Mediocre

Abisola,Oct 2025

LOS - CDG

The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.

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 9h 55m. Delta provides one of the quickest options available for as low as $828. The distance from Chicago to Portsmouth is about 3921 mi.

  • 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 Royal Jordanian (76%), Aer Lingus (73%) or American Airlines (71%) 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 $388. On average you can expect to pay $2,612. The most popular route, (Chicago O'Hare Intl - Southampton Eastleigh), can usually be booked for $828.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Portsmouth (average of $391). Flying from Chicago to Portsmouth in July is currently the most expensive (average of $613). 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.

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Alternative routes for Chicago to Portsmouth

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$51Average$632FlexibilityNo cancel feeOn-time62%
SWISSCheapest$257Average$701FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$338Average$575FlexibilityNo cancel feeOn-time77%
DeltaCheapest$345Average$949FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$430Average$947FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$450Average$660FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$479Average$658FlexibilityNo cancel feeOn-time76%
British AirwaysCheapest$502Average$795FlexibilityNo cancel feeOn-time70%
Aer LingusCheapest$503Average$988FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$544Average$776FlexibilityNo cancel feeOn-time76%

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