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$311+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LHR
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$802
(Delta)

One-way from

$311
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$750
Provider with most accurate pricing for Chicago (CHI)-London (LON) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-London (LON) flights.
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From Chicago (CHI) to Portsmouth
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One-way flight from Chicago (CHI) to Portsmouth
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Highest demand for flights based on searches. 17% potential increase in price ($155 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 1, 2025.

This EaseMyTrip deal was found by Cheapflights users on 4/29. 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 EaseMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:00 pmORD - SOU
2 stops20h 50mVirgin Atlantic
Fri 1/99:00 amSOU - ORD
2 stops18h 14mVirgin Atlantic
Deal found 4/29$1,054
This KLM deal was found by Cheapflights users on 4/28. 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.
Tue 6/104:20 pmORD - SOU
1 stop10h 25mKLM
Tue 6/175:35 pmSOU - ORD
1 stop26h 35mKLM
Deal found 4/28$1,077
This Delta deal was found by Cheapflights users on 4/30. 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 6/106:20 pmMDW - SOU
2 stops16h 40mDelta
Tue 6/179:20 amSOU - MDW
2 stops15h 21mDelta
Deal found 4/30$1,092
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 7/49:28 pmORD - SOU
2 stops34h 52mMultiple Airlines
Mon 7/148:00 pmSOU - ORD
1 stop24h 00mMultiple Airlines
Deal found 4/29$1,095
This SmartFares deal was found by Cheapflights users on 4/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1210:26 amMDW - SOU
2 stops16h 19mMultiple Airlines
Thu 6/195:35 pmSOU - MDW
2 stops31h 06mMultiple Airlines
Deal found 4/29$1,184
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 5/234:20 pmORD - SOU
1 stop10h 25mDelta
Fri 6/69:20 amSOU - ORD
1 stop10h 50mDelta
Deal found 4/29$1,204
This KAYAK deal was found by Cheapflights users on 4/30. 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.
Wed 5/149:15 pmORD - SOU
1 stop13h 20mAer Lingus
Wed 5/218:00 pmSOU - ORD
1 stop24h 00mAer Lingus
Deal found 4/30$1,211
This Netflights deal was found by Cheapflights users on 4/29. 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 Netflights is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/139:24 amMDW - SOU
2 stops26h 06mKLM
Fri 6/209:20 amSOU - MDW
2 stops15h 21mKLM
Deal found 4/29$1,472
This EaseMyTrip deal was found by Cheapflights users on 4/29. 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 EaseMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:40 pmMDW - SOU
2 stops19h 10mVirgin Atlantic
Fri 1/99:00 amSOU - MDW
2 stops18h 46mVirgin Atlantic
Deal found 4/29$1,555
This British Airways deal was found by Cheapflights users on 4/30. 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.
Wed 9/1010:35 pmORD - SOU
2 stops14h 50mBritish Airways
Sun 9/149:10 amSOU - ORD
1 stop15h 50mBritish Airways
Deal found 4/30$2,130

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 May 1, 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

Tue 6/10

4:20 pm-8:45 am

1 stop10h 25m

Southampton Eastleigh

Tue 6/17

5:35 pm-2:10 pm

1 stop26h 35m

$1,077

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Tue 6/10

6:20 pm-5:00 pm

2 stops16h 40m

Southampton Eastleigh

Tue 6/17

9:20 am-6:41 pm

2 stops15h 21m

$1,092

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Fri 7/4

9:28 pm-2:20 pm

2 stops34h 52m

Southampton Eastleigh

Mon 7/14

8:00 pm-2:00 pm

1 stop24h 00m

$1,095

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Thu 6/12

4:20 pm-8:45 am

1 stop10h 25m

Southampton Eastleigh

Thu 6/19

9:20 am-2:10 pm

1 stop10h 50m

$1,109

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Thu 6/12

10:26 am-8:45 am

2 stops16h 19m

Southampton Eastleigh

Thu 6/19

5:35 pm-6:41 pm

2 stops31h 06m

$1,184

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Fri 5/23

4:20 pm-8:45 am

1 stop10h 25m

Southampton Eastleigh

Fri 6/6

9:20 am-2:10 pm

1 stop10h 50m

$1,204

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Wed 5/14

9:15 pm-4:35 pm

1 stop13h 20m

Southampton Eastleigh

Wed 5/21

8:00 pm-2:00 pm

1 stop24h 00m

$1,211

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Fri 6/13

9:24 am-5:30 pm

2 stops26h 06m

Southampton Eastleigh

Fri 6/20

9:20 am-6:41 pm

2 stops15h 21m

$1,472

ChicagoSouthampton

MDW - SOU

MDWSOU

Chicago Midway

Sat 6/14

9:24 am-8:45 am

2 stops17h 21m

Southampton Eastleigh

Sat 6/21

6:05 pm-6:02 pm

2 stops29h 57m

$1,791

ChicagoSouthampton

ORD - SOU

ORDSOU

Chicago O'Hare Intl

Wed 9/10

10:35 pm-7:25 pm

2 stops14h 50m

Southampton Eastleigh

Sun 9/14

9:10 am-7:00 pm

1 stop15h 50m

$2,130

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 20 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, 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 $1,103). 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 May 1, 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 May 1, 2025.

The most flights from CHI to P0R are scheduled on a Monday (57 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (50 on average).

Rainfall in Portsmouth by month

Plan your trip to Portsmouth by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portsmouth ranges from 1.0 - 3.0 inches per month. December is typically the wettest month, when rainfall can reach 3.0 in. July is typically the driest time to visit Portsmouth when rainfall is around 1.0 in.

Temperature in Portsmouth by month

Plan your trip to Portsmouth by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portsmouth, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 64.4 F. Travelers looking to avoid the cold should look outside of December, when temperatures are typically at their lowest (around 39.2 F).

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 May 1, 2025.
See what other customers who have flown with Delta, KLM and Virgin Atlantic from Chicago to Portsmouth have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,334 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Virgin Atlantic
7.4
Good
643 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,245 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Aer Lingus
7.0
Good
1,076 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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?

    $491 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Aer Lingus and KLM, with prices starting from $506 and $546, 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 Royal Jordanian (88%), Gulf Air (82%) or Malaysia Airlines (79%) 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 $398. On average you can expect to pay $2,577. The most popular route, (Chicago O'Hare Intl - Southampton Eastleigh), can usually be booked for $851.

  • 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 $1,103). 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

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$257Average$678FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$381Average$594FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$460Average$911FlexibilityNo cancel feeOn-time76%
IcelandairCheapest$468Average$622FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$506Average$775FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$516Average$717FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$554Average$746FlexibilityNo cancel feeOn-time67%
FinnairCheapest$559Average$712FlexibilityNo cancel feeOn-time76%
IberiaCheapest$578Average$854FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$585Average$804FlexibilityNo cancel feeOn-timeN/A

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