$79 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 10/21. 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

Sat, Oct 4 - Mon, Oct 6
JetBlue Logo
8:00 am - 9:56 amBOS-ORF
1h 56mnonstop
JetBlue Logo
10:25 am - 12:06 pmORF-BOS
1h 41mnonstop
$147JetBlue
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Thu, Oct 2 - Sat, Oct 4
Delta Logo
9:29 am - 11:18 amBOS-ORF
1h 49mnonstop
Delta Logo
5:30 pm - 7:26 pmORF-BOS
1h 56mnonstop
$157Delta
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Wed, Oct 22 - Mon, Oct 27
Southwest Logo
5:30 am - 11:05 amBOS-ORF
5h 35m1 stop
Southwest Logo
7:10 pm - 12:40 amORF-BOS
5h 30m1 stop
$162Southwest
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Mon, Sep 29 - Fri, Oct 3
American Airlines Logo
6:30 am - 12:14 pmBOS-ORF
5h 44m1 stop
American Airlines Logo
6:00 am - 12:16 pmORF-BOS
6h 16m1 stop
$163American Airlines
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Sat, Oct 4 - Mon, Oct 6
Southwest Logo
5:05 am - 9:20 amBOS-ORF
4h 15m1 stop
Southwest Logo
7:10 pm - 12:40 amORF-BOS
5h 30m1 stop
$167Southwest
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Sun, Oct 19 - Mon, Oct 20
JetBlue Logo
7:00 am - 8:59 amBOS-ORF
1h 59mnonstop
JetBlue Logo
10:25 am - 12:06 pmORF-BOS
1h 41mnonstop
$182JetBlue
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Wed, Dec 3 - Sun, Dec 7
Spirit Airlines Logo
6:15 am - 7:37 pmBOS-ORF
13h 22m1 stop
Spirit Airlines Logo
3:07 pm - 11:25 pmORF-BOS
8h 18m1 stop
$184Spirit Airlines
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Fri, Jan 9 - Sun, Jan 11
Spirit Airlines Logo
6:00 am - 2:12 pmBOS-ORF
8h 12m1 stop
Spirit Airlines Logo
3:07 pm - 11:25 pmORF-BOS
8h 18m1 stop
$186Spirit Airlines
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Wed, Oct 1 - Sun, Oct 5
American Airlines Logo
7:28 am - 12:12 pmBOS-ORF
4h 44m1 stop
American Airlines Logo
9:51 am - 3:59 pmORF-BOS
6h 08m1 stop
$192American Airlines
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Thu, Oct 2 - Sat, Oct 4
Delta Logo
9:29 am - 11:18 amBOS-ORF
1h 49mnonstop
Delta Logo
1:00 pm - 6:28 pmORF-BOS
5h 28m1 stop
$212Delta
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Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 31% 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 44m.

  • How many flights are there between Boston and Chesapeake?

    3 direct flights run between Boston and Chesapeake on a daily basis. On average, there are about 22 departures each week.

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

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

  • 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 Southwest for $79. JetBlue offered a round-trip connection from $147 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 69 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 July.

Reviews of the 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.
7.9
DeltaOverall score based on 7957 reviews
8.5Crew
7.3Food
8.2Boarding
7.9Comfort
7.9Entertainment
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

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!

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

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

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