$94 Find Cheap Flights from Chicago to Portsmouth - Compare and Save

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 7/7. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$176
Typical prices: $184-$322
JetBlue
Fri 7/31Mon 8/3
ORD - BOS • 1 stop
Cheapest non-stop
$176
Typical prices: $339-$178
American Airlines
Thu 8/13Sun 8/16
ORD - BOS • Non-stop
Arrival airport
You can't fly directly to Portsmouth. It is served by Boston (BOS), located 50.3 miles from Portsmouth.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Portsmouth (CHI-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Portsmouth that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Portsmouth

Fri, Jul 31 - Mon, Aug 3
JetBlue Logo
5:27 pm - 11:59 pm
ORD
-
BOS
5h 32m
1 stop
JetBlue Logo
5:01 am - 8:52 am
BOS
-
ORD
4h 51m
1 stop
$176JetBlue
Fri, Jul 17 - Tue, Aug 4
JetBlue Logo
6:00 am - 2:43 pm
ORD
-
BOS
7h 43m
1 stop
JetBlue Logo
5:01 am - 8:50 am
BOS
-
ORD
4h 49m
1 stop
$177JetBlue
Sat, Sep 5 - Wed, Sep 9
Delta Logo
7:30 am - 10:59 am
ORD
-
BOS
2h 29mnonstop
Delta Logo
7:30 am - 9:24 am
BOS
-
ORD
2h 54mnonstop
$178Delta
Fri, Jul 3 - Sat, Jul 11
Delta Logo
4:00 pm - 7:43 pm
ORD
-
BOS
2h 43mnonstop
Delta Logo
7:59 pm - 9:59 pm
BOS
-
ORD
3h 00mnonstop
$179Delta
Fri, Jul 10 - Wed, Jul 15
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$179Southwest
Sat, Jul 4 - Sat, Jul 11
United Airlines Logo
8:43 am - 2:40 pm
ORD
-
BOS
4h 57m
1 stop
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
$180United Airlines
Tue, Jul 21 - Wed, Jul 22
Southwest Logo
5:30 pm - 11:25 pm
MDW
-
BOS
4h 55m
1 stop
Southwest Logo
7:30 am - 9:10 am
BOS
-
MDW
2h 40mnonstop
$180Southwest
Fri, Sep 4 - Tue, Sep 8
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
5:01 am - 8:48 am
BOS
-
ORD
4h 47m
1 stop
$181JetBlue
Fri, Aug 7 - Tue, Aug 11
JetBlue Logo
6:00 am - 11:21 am
ORD
-
BOS
4h 21m
1 stop
JetBlue Logo
2:45 pm - 9:55 pm
BOS
-
ORD
8h 10m
1 stop
$182JetBlue
Mon, Jun 29 - Sat, Jul 4
Southwest Logo
9:20 am - 12:40 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:40 pm - 7:30 pm
BOS
-
MDW
2h 50mnonstop
$182Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$94
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 2% 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 10m.

  • 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 608 departures each week.

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

    Consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays 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 5 days, the cheapest one-way ticket between Chicago and Portsmouth found on KAYAK was with JetBlue for $65. JetBlue offered a round-trip connection from $68 and Delta from $79.

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 54 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 March, April and May. The cheapest month to fly is January.

Reviews of the 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.
7.9
SouthwestOverall score based on 4236 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

Everything you need to know for your flight from Chicago to Portsmouth

Complete your trip to Portsmouth with a hotel stay or car rental