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Find cheap flights from Chicago to Portsmouth from $27

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portsmouth departing on 7/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 7/1
Mon 7/8

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In the last 7 days travelers have searched 42,335,261 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

October

Cheapest flight

$27
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago O'Hare Airport to Boston

When to book flights from Chicago to Portsmouth

Are your dates flexible? Find out the best times to travel from Chicago to Portsmouth based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Portsmouth

  • Which airports will I be using when flying from Chicago to Portsmouth?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Portsmouth does not have its own airport so you’ll be flying into nearby Boston Logan Intl airport, which is 50.3 mi away.

  • How long does a flight from Chicago to Portsmouth take?

    Direct flights cover the 850 miles separating Chicago and Portsmouth in about 2h 18m.

  • How many flights are there between Chicago and Portsmouth?

    86 direct flights run between Chicago and Portsmouth on a daily basis. On average, there are about 606 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Portsmouth?

    Consider leaving on a Tuesday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Portsmouth?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Portsmouth.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Portsmouth?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portsmouth from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Portsmouth?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portsmouth with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Portsmouth?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portsmouth from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Portsmouth?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Portsmouth found on KAYAK was with Spirit Airlines for $27. Spirit Airlines offered a round-trip connection from $40 and Frontier from $116.

See more FAQs

Top tips for finding cheap flights from Chicago to Portsmouth

  • There is no airport in Portsmouth. Instead, you’ll be flying into Boston Logan Airport when flying between Chicago and Portsmouth.
  • The cheapest flight from Chicago to Portsmouth was found 84 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is January.
See more tips

Top 5 airlines serving Chicago to Portsmouth

 
Need help choosing which airline to fly with from Chicago to Portsmouth? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10410 reviews
7.9Comfort
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
Airline reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

Book cheap flights from Chicago to Portsmouth

Recent round-trip flight deals

6/11Tue
nonstopSpirit Airlines
2h 28mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$40
9/11Wed
nonstopSpirit Airlines
2h 18mORD-BOS
9/14Sat
nonstopSpirit Airlines
2h 33mBOS-ORD
$50
8/28Wed
1 stopFrontier
10h 26mMDW-BOS
8/31Sat
1 stopFrontier
10h 03mBOS-MDW
$116
6/11Tue
1 stopFrontier
7h 42mMDW-BOS
6/12Wed
1 stopFrontier
25h 15mBOS-MDW
$120
6/15Sat
nonstopJetBlue
2h 26mORD-BOS
6/17Mon
nonstopJetBlue
2h 57mBOS-ORD
$157
6/12Wed
nonstopAmerican Airlines
2h 26mORD-BOS
6/14Fri
nonstopAmerican Airlines
2h 55mBOS-ORD
$160
7/6Sat
nonstopJetBlue
2h 26mORD-BOS
7/13Sat
nonstopJetBlue
2h 54mBOS-ORD
$162
6/15Sat
nonstopDelta
2h 31mORD-BOS
6/19Wed
nonstopDelta
2h 57mBOS-ORD
$167
6/11Tue
nonstopAmerican Airlines
2h 25mORD-BOS
6/14Fri
nonstopAmerican Airlines
2h 55mBOS-ORD
$170
6/13Thu
nonstopDelta
2h 28mORD-BOS
6/21Fri
nonstopDelta
2h 57mBOS-ORD
$187

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Recent one-way flight deals

7/2Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$27
7/15Mon
nonstopSpirit Airlines
2h 26mORD-BOS
$29
9/3Tue
nonstopDelta
2h 26mORD-BOS
$69
8/6Tue
1 stopJetBlue
4h 39mORD-BOS
$78
9/1Sun
nonstopAmerican Airlines
2h 18mORD-BOS
$80
6/11Tue
nonstopJetBlue
2h 33mORD-BOS
$82
8/29Thu
nonstopDelta
2h 26mORD-BOS
$89
6/7Fri
1 stopUnited Airlines
5h 22mORD-BOS
$103
6/8Sat
1 stopUnited Airlines
5h 04mORD-BOS
$108
9/1Sun
1 stopAmerican Airlines
6h 19mORD-BOS
$128

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Last minute flights from Chicago to Portsmouth

Last minute flight, train and bus deals

6/6Thu
nonstopSpirit Airlines
2h 28mORD-BOS
6/11Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
$78
6/6Thu
nonstopSpirit Airlines
2h 28mORD-BOS
6/11Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
$84
6/4Tue
nonstopAmerican Airlines
2h 26mORD-BOS
6/11Tue
nonstopAmerican Airlines
2h 55mBOS-ORD
$250
6/3Mon
multi-stopAmerican Airlines
4h 44mORD-BOS
6/7Fri
nonstopAmerican Airlines
2h 55mBOS-ORD
$258
6/5Wed
multi-stopUnited Airlines
6h 15mORD-BOS
6/8Sat
multi-stopUnited Airlines
5h 35mBOS-ORD
$269
6/3Mon
nonstopJetBlue
2h 26mORD-BOS
6/9Sun
nonstopJetBlue
2h 54mBOS-ORD
$282
6/2Sun
multi-stopDelta
6h 59mORD-BOS
6/7Fri
nonstopDelta
2h 57mBOS-ORD
$290
6/2Sun
nonstopDelta
2h 36mORD-BOS
6/7Fri
nonstopDelta
2h 57mBOS-ORD
$295
6/6Thu
nonstopJetBlue
2h 33mORD-BOS
6/17Mon
nonstopJetBlue
2h 57mBOS-ORD
$302
6/3Mon
nonstopUnited Airlines
2h 35mORD-BOS
6/9Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$320

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Flights to Portsmouth