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Find cheap flights from Chicago to Portsmouth from $46

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portsmouth departing on 6/5. 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
Sun 6/9
Sun 6/16

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Good to know

Low season

January

High season

October

Cheapest flight

$46
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 1% 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?

    99 direct flights run between Chicago and Portsmouth on a daily basis. On average, there are about 695 departures each week.

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

    Consider leaving on a Wednesday and avoid Thursdays 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 Wednesdays.

  • 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 $58. Spirit Airlines offered a round-trip connection from $46 and Frontier from $100.

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 10768 reviews
7.9Comfort
7.4Food
8.6Crew
8.2Boarding
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Everything was good except for deplaning in NY. Took way too long!!

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.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

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

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

Book cheap flights from Chicago to Portsmouth

Recent round-trip flight deals

6/5Wed
nonstopSpirit Airlines
2h 29mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$46
6/5Wed
nonstopSpirit Airlines
2h 29mORD-BOS
6/8Sat
nonstopSpirit Airlines
2h 54mBOS-ORD
$50
5/29Wed
1 stopFrontier
13h 44mORD-BOS
6/1Sat
1 stopFrontier
14h 16mBOS-ORD
$100
5/22Wed
1 stopFrontier
5h 07mORD-BOS
6/1Sat
1 stopFrontier
14h 16mBOS-ORD
$122
5/31Fri
nonstopDelta
2h 36mORD-BOS
6/4Tue
nonstopDelta
2h 55mBOS-ORD
$163
6/1Sat
nonstopDelta
2h 31mORD-BOS
6/3Mon
nonstopDelta
2h 55mBOS-ORD
$173
5/25Sat
nonstopAmerican Airlines
2h 20mORD-BOS
5/30Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$183
5/25Sat
nonstopJetBlue
2h 26mORD-BOS
5/29Wed
nonstopJetBlue
2h 54mBOS-ORD
$189
6/8Sat
nonstopJetBlue
2h 26mORD-BOS
6/11Tue
nonstopJetBlue
2h 54mBOS-ORD
$193
5/31Fri
1 stopAmerican Airlines
4h 44mORD-BOS
6/4Tue
nonstopAmerican Airlines
2h 56mBOS-ORD
$196

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Recent one-way flight deals

5/18Sat
1 stopFrontier
11h 35mMDW-BOS
$58
6/11Tue
1 stopFrontier
7h 42mMDW-BOS
$59
8/8Thu
nonstopDelta
2h 12mORD-BOS
$95
5/31Fri
nonstopJetBlue
2h 26mORD-BOS
$99
5/25Sat
1 stopUnited Airlines
5h 19mORD-BOS
$104
6/28Fri
nonstopUnited Airlines
2h 35mORD-BOS
$112
5/28Tue
nonstopJetBlue
2h 26mORD-BOS
$115
6/30Sun
1 stopAmerican Airlines
4h 05mORD-BOS
$128
5/24Fri
1 stopAmerican Airlines
4h 15mORD-BOS
$129
5/24Fri
nonstopDelta
2h 36mORD-BOS
$130

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Last minute flights from Chicago to Portsmouth

Last minute flight, train and bus deals

5/15Wed
multi-stopSpirit Airlines
13h 16mORD-BOS
5/18Sat
multi-stopSpirit Airlines
14h 07mBOS-ORD
$162
5/15Wed
multi-stop
13h 16mORD-BOS
5/20Mon
multi-stop
16h 04mBOS-ORD
$172
5/15Wed
multi-stopAmerican Airlines
4h 44mORD-BOS
5/19Sun
nonstopAmerican Airlines
2h 52mBOS-ORD
$247
5/15Wed
multi-stopJetBlue
6h 26mORD-BOS
5/18Sat
nonstopJetBlue
2h 54mBOS-ORD
$266
5/15Wed
nonstopAmerican Airlines
2h 17mORD-BOS
5/23Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$279
5/14Tue
nonstopJetBlue
2h 29mORD-BOS
5/15Wed
nonstopJetBlue
2h 54mBOS-ORD
$283
5/12Sun
nonstopUnited Airlines
2h 23mORD-BOS
5/16Thu
multi-stopUnited Airlines
5h 38mBOS-ORD
$292
5/13Mon
nonstopDelta
2h 27mORD-BOS
5/18Sat
nonstopDelta
2h 52mBOS-ORD
$294
5/12Sun
nonstopUnited Airlines
2h 23mORD-BOS
5/16Thu
nonstopUnited Airlines
2h 53mBOS-ORD
$297
5/14Tue
multi-stopDelta
6h 34mORD-BOS
5/18Sat
nonstopDelta
2h 52mBOS-ORD
$303

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Flights to Portsmouth