$52 Find Cheap Flights from Boston to Chesapeake

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Chesapeake departing on 7/11. 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 Flights from Boston to Chesapeake (BOS-ORF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Chesapeake 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 Boston to Chesapeake

Fri, Jul 25 - Mon, Jul 28
Allegiant Air Logo
12:51 pm - 2:30 pmBOS-ORF
1h 39mnonstop
Allegiant Air Logo
10:25 am - 12:01 pmORF-BOS
1h 36mnonstop
$64Allegiant Air
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Fri, Jul 25 - Mon, Jul 28
Allegiant Air Logo
12:51 pm - 2:30 pmBOS-ORF
1h 39mnonstop
Allegiant Air Logo
10:25 am - 12:01 pmORF-BOS
1h 36mnonstop
$65Allegiant Air
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Thu, Jul 10 - Thu, Jul 17
Delta Logo
9:30 am - 11:23 amBOS-ORF
1h 53mnonstop
Delta Logo
12:04 pm - 1:59 pmORF-BOS
1h 55mnonstop
$157Delta
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Sat, Oct 11 - Wed, Oct 15
JetBlue Logo
8:05 am - 9:40 amBOS-ORF
1h 35mnonstop
JetBlue Logo
10:25 am - 11:54 amORF-BOS
1h 29mnonstop
$162JetBlue
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Tue, Jul 8 - Thu, Jul 10
JetBlue Logo
3:18 pm - 5:02 pmBOS-ORF
1h 44mnonstop
JetBlue Logo
5:57 pm - 7:37 pmORF-BOS
1h 40mnonstop
$167JetBlue
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Fri, Jun 27 - Sun, Jun 29
Spirit Airlines Logo
5:45 am - 12:56 pmBOS-ORF
7h 11m1 stop
Spirit Airlines Logo
11:34 am - 11:47 pmORF-BOS
12h 13m1 stop
$176Spirit Airlines
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Mon, Jun 30 - Tue, Jul 1
Delta Logo
2:25 pm - 4:19 pmBOS-ORF
1h 54mnonstop
Delta Logo
12:04 pm - 1:59 pmORF-BOS
1h 55mnonstop
$182Delta
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Fri, Aug 15 - Mon, Aug 18
Spirit Airlines Logo
6:30 am - 12:44 pmBOS-ORF
6h 14m1 stop
Spirit Airlines Logo
1:39 pm - 10:34 pmORF-BOS
8h 55m1 stop
$183Spirit Airlines
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Fri, Jul 4 - Mon, Jul 7
American Airlines Logo
11:05 am - 2:45 pmBOS-ORF
3h 40m1 stop
American Airlines Logo
6:10 pm - 10:19 pmORF-BOS
4h 09m1 stop
$208American Airlines
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Mon, Jun 30 - Wed, Jul 2
American Airlines Logo
4:55 pm - 10:00 pmBOS-ORF
5h 05m1 stop
American Airlines Logo
9:25 am - 4:03 pmORF-BOS
6h 38m1 stop
$217American Airlines
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$52
Best time to beat the crowds but there is an average 29% increase in price.
Most popular time to fly and prices are also 29% lower on average.
Flight from Boston to Norfolk

When to book flights from Boston to Chesapeake

Are your dates flexible? Find out the best times to travel from Boston to Chesapeake 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 Boston to Chesapeake

  • Which airports will I be using when flying from Boston to Chesapeake?

    When flying out of Boston you’ll be using Boston Logan Intl. Chesapeake does not have its own airport so you’ll be flying into nearby Norfolk airport, which is 10.1 mi away.

  • How long does a flight from Boston to Chesapeake take?

    Direct flights cover the 468 miles separating Boston and Chesapeake in about 1h 35m.

  • How many flights are there between Boston and Chesapeake?

    4 direct flights run between Boston and Chesapeake on a daily basis. On average, there are about 32 departures each week.

  • What’s the cheapest day of the week to fly between Boston and Chesapeake?

    Consider leaving on a Friday and avoid Tuesdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

  • How does KAYAK find such low prices on flights from Boston to Chesapeake?

    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 Boston to Chesapeake.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chesapeake from Boston 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 Boston to Chesapeake?

    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 Chesapeake with an airline and back to Boston with another airline.

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

    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 Chesapeake from Boston 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 Boston to Chesapeake?

    In the last 72 hours, the cheapest one-way ticket between Boston and Chesapeake found on KAYAK was with Allegiant Air for $52. Allegiant Air offered a round-trip connection from $64 and Delta from $157.

Top tips for finding cheap flights from Boston to Chesapeake

  • There is no airport in Chesapeake. Instead, you’ll be flying into Norfolk Airport when flying between Boston and Chesapeake.
  • The cheapest flight from Boston to Chesapeake was found 67 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 November, December and January. The cheapest month to fly is September.

Top 5 airlines serving Boston to Chesapeake

 
Need help choosing which airline to fly with from Boston to Chesapeake? 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 7946 reviews
7.9Entertainment
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Everything you need to know for your flight from Boston to Chesapeake

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