$66 Find Cheap Flights from Chicago to Portsmouth

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 2/25. 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
$130
Overall average: $246
Southwest
Sat 3/7Sun 3/8
MDW - BOS • 1 stop
Cheapest non-stop
$131
Typical prices: $166-$359
United Airlines
Fri 4/17Sun 4/19
ORD - BOS • Non-stop
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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

Sat, Mar 7 - Sun, Mar 8
Southwest Logo
5:40 pm - 11:05 pm
MDW
-
BOS
4h 25m
1 stop
Southwest Logo
7:05 am - 9:00 am
BOS
-
MDW
2h 55mnonstop
$130Southwest
Fri, Apr 17 - Sun, Apr 19
United Airlines Logo
6:00 am - 9:25 am
ORD
-
BOS
2h 25mnonstop
United Airlines Logo
7:00 am - 9:00 am
BOS
-
ORD
3h 00mnonstop
$131United Airlines
Thu, Feb 26 - Mon, Mar 2
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
JetBlue Logo
5:32 pm - 10:59 pm
BOS
-
ORD
6h 27m
1 stop
$132JetBlue
Sat, Feb 14 - Wed, Feb 18
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
$133JetBlue
Sat, Feb 14 - Wed, Feb 18
Frontier Logo
6:00 am - 12:29 am
MDW
-
BOS
17h 29m
1 stop
Frontier Logo
6:00 am - 7:07 pm
BOS
-
MDW
14h 07m
1 stop
$134Frontier
Sun, Feb 15 - Thu, Feb 19
American Airlines Logo
7:20 am - 10:48 am
ORD
-
BOS
2h 28mnonstop
American Airlines Logo
6:52 am - 9:03 am
BOS
-
ORD
3h 11mnonstop
$135American Airlines
Mon, Mar 2 - Tue, Mar 3
Frontier Logo
4:42 pm - 1:13 am
ORD
-
BOS
7h 31m
1 stop
Frontier Logo
6:00 am - 4:52 pm
BOS
-
ORD
11h 52m
1 stop
$136Frontier
Fri, Apr 3 - Mon, Apr 6
American Airlines Logo
8:51 pm - 12:11 am
ORD
-
BOS
2h 20mnonstop
American Airlines Logo
5:31 pm - 7:48 pm
BOS
-
ORD
3h 17mnonstop
$137American Airlines
Sat, Feb 28 - Mon, Mar 2
Delta Logo
5:37 pm - 11:26 pm
ORD
-
BOS
4h 49m
1 stop
Delta Logo
6:45 pm - 11:56 pm
BOS
-
ORD
6h 11m
1 stop
$139Delta
Sat, Feb 28 - Tue, Mar 3
Delta Logo
11:45 am - 7:15 pm
MDW
-
BOS
6h 30m
1 stop
Delta Logo
5:25 pm - 10:33 pm
BOS
-
MDW
6h 08m
1 stop
$139Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$66
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 3% 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?

    93 direct flights run between Chicago and Portsmouth on a daily basis. On average, there are about 657 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 Mondays 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 $57. JetBlue offered a round-trip connection from $61 and Spirit Airlines 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 89 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.
8.0
SouthwestOverall score based on 4267 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

10.0 ExcellentAnonymous, Feb 2026
MSY - PHX
Read more Southwest reviews

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

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

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