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Find cheap flights from Boston to Chesapeake from $30

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 5/21. 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.
1 adult
0 bags
Sat 6/15
Sat 6/22

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In the last 7 days travelers have searched 42,211,976 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

June

Cheapest flight

$30
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 21% 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 37m.

  • 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 23 departures each week.

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

    Consider leaving on a Saturday and avoid Tuesdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Wednesdays 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 Spirit Airlines for $30. Spirit Airlines offered a round-trip connection from $88 and Allegiant Air from $114.

See more FAQs

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 82 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be August, September and October. The cheapest month to fly is May.
See more tips

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 10673 reviews
7.4Food
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

They did a fine job. Can't wait to use Delta in the future.

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Flight attendant was incredible. Very efficient, friendly and pleasant. Patricia was one of the best I have ever seen. Please give her a big raise!

LIT to DFW - 3 hours late; the entire plane had been boarded before they told us there was a delay due to a weather-related ground stop in Dallas. DFW to MAY - 2+ hours late due to A/C needing to be repaired after everyone had boarded, then when we finally reach the runway, the First Officer timed out and we had to taxi all the way back to the gate and wait for a new one. I arrived in New Orleans 5+ hours later than I should have. Return flights were completely cancelled; rebooked through the app to fly through CLT instead of DFW. MSY to CLT had no issues, but CLT to LIT was delayed 1.25 hrs because flight attendants had not arrived to the airport yet. At least they didn’t make us all sit on the plane to wait for them. I should have driven.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in-flight WiFi. Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay that much for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a shitty attitude for no reason, nor will they act the way this woman did. Unacceptable.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Delayed almost 4 hours for a 45 minute flight with no explanation.

The flight was excellent, provided that we had inclement weather. We departed earlier than scheduled and arrived early. There was a little turbulence, but nothing to be worried about.

delayed delayed delayed. was supposed to have a 2 hour layover and very nearly missed my connection.

Despite a bumpy flight the pilot was great. The rest of the crew on the other hand couldn’t care less if a passenger would colapse and die. Horrible service, robot like, lifeless…

No service due to turbulence. No entertainment on this type of aircraft. But nice old comfortable seats.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Book cheap flights from Boston to Chesapeake

Recent round-trip flight deals

5/25Sat
nonstopSpirit Airlines
1h 44mBOS-ORF
5/28Tue
nonstopSpirit Airlines
1h 47mORF-BOS
$88
6/2Sun
nonstopSpirit Airlines
1h 46mBOS-ORF
6/6Thu
nonstopSpirit Airlines
1h 41mORF-BOS
$89
6/3Mon
1 stopSpirit Airlines
11h 23mBOS-ORF
6/8Sat
nonstopSpirit Airlines
1h 45mORF-BOS
$91
6/15Sat
nonstopSpirit Airlines
1h 46mBOS-ORF
6/16Sun
nonstopSpirit Airlines
1h 41mORF-BOS
$93
5/31Fri
nonstopSpirit Airlines
1h 46mBOS-ORF
6/2Sun
nonstopSpirit Airlines
1h 45mORF-BOS
$94
6/14Fri
nonstop
1h 37mBOS-ORF
6/15Sat
nonstop
1h 45mORF-BOS
$96
6/5Wed
1 stop
3h 50mBOS-ORF
6/8Sat
nonstop
1h 45mORF-BOS
$100
5/24Fri
nonstopAllegiant Air
1h 40mBOS-ORF
5/27Mon
nonstopAllegiant Air
1h 43mORF-BOS
$114
8/3Sat
1 stopAmerican Airlines
3h 44mBOS-ORF
8/10Sat
1 stopAmerican Airlines
4h 49mORF-BOS
$226
8/1Thu
1 stopAmerican Airlines
5h 49mBOS-ORF
8/6Tue
1 stopAmerican Airlines
4h 01mORF-BOS
$240

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Recent one-way flight deals

5/21Tue
nonstopSpirit Airlines
1h 45mBOS-ORF
$30
6/24Mon
nonstopSpirit Airlines
1h 44mBOS-ORF
$44
6/21Fri
nonstopAllegiant Air
1h 37mBOS-ORF
$56
7/19Fri
nonstopAllegiant Air
1h 39mBOS-ORF
$61
7/24Wed
1 stopAmerican Airlines
6h 45mBOS-ORF
$118
7/9Tue
1 stopAmerican Airlines
4h 14mBOS-ORF
$119
7/2Tue
nonstopDelta
1h 46mBOS-ORF
$134
6/21Fri
1 stopUnited Airlines
4h 56mBOS-ORF
$143
6/22Sat
1 stopUnited Airlines
3h 59mBOS-ORF
$183
7/7Sun
nonstopDelta
1h 50mBOS-ORF
$344

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Last minute flights from Boston to Chesapeake

Last minute flight, train and bus deals

5/21Tue
nonstopSpirit Airlines
1h 45mBOS-ORF
5/26Sun
nonstopSpirit Airlines
1h 45mORF-BOS
$74
5/21Tue
nonstopSpirit Airlines
1h 45mBOS-ORF
5/22Wed
nonstopSpirit Airlines
1h 45mORF-BOS
$163
5/19Sun
multi-stop
12h 13mBOS-ORF
5/24Fri
nonstop
1h 45mORF-BOS
$326
5/21Tue
multi-stop
27h 29mBOS-ORF
5/26Sun
multi-stop
11h 00mORF-BOS
$356
5/21Tue
multi-stopDelta
5h 31mBOS-ORF
5/22Wed
multi-stopDelta
6h 08mORF-BOS
$384
5/21Tue
multi-stopDelta
5h 31mBOS-ORF
5/28Tue
multi-stopDelta
6h 20mORF-BOS
$430
5/21Tue
multi-stopAmerican Airlines
4h 02mBOS-ORF
5/28Tue
multi-stopAmerican Airlines
4h 49mORF-BOS
$469
5/21Tue
multi-stopAmerican Airlines
4h 02mBOS-ORF
5/28Tue
multi-stopAmerican Airlines
4h 49mORF-BOS
$470
5/21Tue
multi-stopUnited Airlines
5h 17mBOS-ORF
5/22Wed
multi-stopUnited Airlines
6h 27mORF-BOS
$642
5/21Tue
multi-stopUnited Airlines
5h 17mBOS-ORF
5/28Tue
multi-stopUnited Airlines
10h 46mORF-BOS
$647

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