$50 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 1/14. 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.
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Cheap Flight Deals 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.

Recent round-trip flight deals from Chicago to Portsmouth

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Portsmouth.
Discover the best prices and deals for you by selecting your travel dates.
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3:00 pm - 12:30 amORD-BOS
8h 30m1 stop
6:00 am - 11:47 amBOS-ORD
6h 47m1 stop
$100Frontier
Find Deal
Tue, Jan 14 - Wed, Jan 15
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
6:00 am - 5:57 pmBOS-MDW
12h 57m1 stop
$100Frontier
Find Deal
Tue, Jan 14 - Wed, Jan 15
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
6:10 am - 8:14 amBOS-ORD
3h 04mnonstop
$157JetBlue
Find Deal
Tue, Jan 14 - Wed, Jan 15
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
$158American Airlines
Find Deal
Thu, Jan 9 - Mon, Jan 13
9:05 am - 12:23 pmORD-BOS
2h 18mnonstop
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
$166JetBlue
Find Deal
Thu, Jan 16 - Thu, Jan 23
1:55 pm - 5:17 pmORD-BOS
2h 22mnonstop
6:00 am - 8:04 amBOS-ORD
3h 04mnonstop
$177United Airlines
Find Deal
Wed, Mar 5 - Sun, Mar 9
10:00 am - 1:16 pmORD-BOS
2h 16mnonstop
6:00 am - 8:15 amBOS-ORD
3h 15mnonstop
$183American Airlines
Find Deal
Sat, Feb 15 - Wed, Feb 19
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
11:45 am - 1:50 pmBOS-ORD
3h 05mnonstop
$184Delta
Find Deal
Mon, Jan 20 - Fri, Jan 24
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
$187Delta
Find Deal
Mon, Jan 20 - Wed, Jan 22
6:00 am - 12:45 pmORD-BOS
5h 45m1 stop
11:01 am - 1:03 pmBOS-ORD
3h 02mnonstop
$209United Airlines
Find Deal
Fri, Mar 14 - Sun, Mar 23

Good to know

Low season

January

High season

October

Cheapest flight

$50
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 9% 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?

    76 direct flights run between Chicago and Portsmouth on a daily basis. On average, there are about 535 departures each week.

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

    Consider leaving on a Tuesday and avoid Fridays 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 Sundays.

  • 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 Frontier for $50. Frontier offered a round-trip connection from $100 and Spirit Airlines from $144.

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 79 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 September.
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 8604 reviews
8.2Boarding
8.6Crew
7.3Food
7.9Comfort
7.9Entertainment
Airline reviews

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

10.0 ExcellentFreddy, Dec 2024JFK - MKE
Read more Delta reviews

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

Like the space, did not like the snack options, there was no power outlet in seats, no entertainment, no flyfi.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Didn't make it dir to delays - no support from United staff

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

I thought since I upgraded my seat I would get some perks. Free water, free snacks. Free carry on luggage.

Seats were surprisingly comfortable, and crew was polite. I did not like the baggage fee prices, the minimal amount of flight choices for my area and the difficulty of the self service bag drop.

Lost MacBook, had time to retrieve, but was told I had no time. Need Silver MacBook back

It’s ridiculous to pay for carry-on luggage. I also wasn’t given an option to specify I have carry on bag at time of ticket purchase. I also could not specify I have carry on luggage at time of online check-in.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

The people were wonderful, but I hated the way they over charged for luggage, especially for stops which were charged the same as starting point to final destination.

First time flying Spirit and I was pleasantly surprised. Service was as advertised. Crew were very professional and friendly and excellent in dealing with a customer who felt ill on the flight.

Delayed fight LAS to LAX. OK, fog in LA, not your fault. But all your staff, onboard in in lounge, speak so fast, enunciate so poorly and often have a accent that it is impossible to understanding anything they are saying.

Very mean staff. No entertainment.. No WiFi, a baby cried for over 3 hours no staff offer to assist. My son $500 computer screen got damaged under the plane due to force check in of my bag. TERRIBLE EXPERIENCE!

Nothing I liked. Seats uncomfortable child behind kicking my seat entire flight. Delayed. Couldn't get free glass of water

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

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