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Find cheap flights from Boston to Chesapeake from $37

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
sab 6/8
sab 6/15

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Good to know

Low season

January

High season

July

Cheapest flight

$37
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 23% 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 Tuesday and avoid Fridays 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 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 Spirit Airlines for $37. Spirit Airlines offered a round-trip connection from $68 and Allegiant Air from $84.

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 10789 reviews
7.4Food
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

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.

8.0 ExcellentEric, May 2024BOS - CUN
Read more about Delta reviews

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.

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.

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.

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.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Terrible! The plane was old and you are required to connect your own device to their Wi-Fi rather than have entertainment options in the back of the seat in front of you. The Wi-Fi went out during the flight and there was only one plug for the devices every two seats. Three out of five surrounding my family did not work. The seats and spaces under them were so small I could not fit my backpack, which I’ve always brought on flights and fit before no problem. The crew were unpleasant and patronizing.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

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

Again, multiple delays and I eventually just canceled and drove!

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

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.

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.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

Book cheap flights from Boston to Chesapeake

Recent round-trip flight deals

5/21mar
nonstopSpirit Airlines
1h 45mBOS-ORF
5/24ven
nonstopSpirit Airlines
1h 45mORF-BOS
$68
5/21mar
1 stopSpirit Airlines
12h 42mBOS-ORF
5/24ven
nonstopSpirit Airlines
1h 45mORF-BOS
$81
9/7sab
nonstopSpirit Airlines
1h 44mBOS-ORF
9/14sab
nonstopSpirit Airlines
1h 45mORF-BOS
$82
6/7ven
nonstopAllegiant Air
1h 37mBOS-ORF
6/14ven
nonstopAllegiant Air
1h 42mORF-BOS
$84
7/8lun
nonstop
1h 39mBOS-ORF
7/17mer
nonstop
1h 45mORF-BOS
$96
6/21ven
nonstop
1h 37mBOS-ORF
6/26mer
nonstop
1h 45mORF-BOS
$99
8/3sab
1 stopAmerican Airlines
3h 53mBOS-ORF
8/10sab
1 stopAmerican Airlines
4h 30mORF-BOS
$224
8/7mer
nonstopDelta
1h 53mBOS-ORF
8/14mer
1 stopDelta
14h 00mORF-BOS
$245
8/7mer
1 stopDelta
9h 44mBOS-ORF
8/12lun
1 stopDelta
5h 33mORF-BOS
$270
7/5ven
1 stopAmerican Airlines
6h 56mBOS-ORF
7/13sab
1 stopAmerican Airlines
4h 45mORF-BOS
$283

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Recent one-way flight deals

5/21mar
1 stopSpirit Airlines
12h 42mBOS-ORF
$37
5/30gio
nonstopSpirit Airlines
1h 46mBOS-ORF
$38
5/25sab
nonstopSpirit Airlines
1h 44mBOS-ORF
$40
6/1sab
nonstopSpirit Airlines
1h 44mBOS-ORF
$41
6/28ven
nonstopAllegiant Air
1h 37mBOS-ORF
$56
7/9mar
nonstopDelta
1h 49mBOS-ORF
$134
5/25sab
1 stopAmerican Airlines
4h 41mBOS-ORF
$158
5/19dom
1 stopAmerican Airlines
3h 36mBOS-ORF
$159
6/29sab
1 stopUnited Airlines
17h 40mBOS-ORF
$219
7/9mar
2 stopsUnited Airlines
12h 30mBOS-ORF
$258

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Last minute flights from Boston to Chesapeake

Last minute flight, train and bus deals

5/10ven
nonstopSpirit Airlines
1h 46mBOS-ORF
5/15mer
nonstopSpirit Airlines
1h 45mORF-BOS
$151
5/14mar
nonstopSpirit Airlines
1h 45mBOS-ORF
5/20lun
nonstopSpirit Airlines
1h 45mORF-BOS
$158
5/11sab
nonstopSpirit Airlines
1h 44mBOS-ORF
5/14mar
nonstopSpirit Airlines
1h 47mORF-BOS
$163
5/10ven
nonstop
1h 46mBOS-ORF
5/15mer
multi-stop
20h 42mORF-BOS
$274
5/10ven
nonstop
1h 46mBOS-ORF
5/12dom
multi-stop
9h 21mORF-BOS
$320
5/14mar
multi-stopDelta
3h 29mBOS-ORF
5/15mer
multi-stopDelta
4h 06mORF-BOS
$384
5/12dom
multi-stopAmerican Airlines
4h 47mBOS-ORF
5/19dom
multi-stopAmerican Airlines
3h 12mORF-BOS
$469
5/12dom
multi-stopUnited Airlines
4h 00mBOS-ORF
5/17ven
multi-stopUnited Airlines
4h 44mORF-BOS
$470
5/11sab
multi-stopAmerican Airlines
5h 42mBOS-ORF
5/11sab
multi-stopAmerican Airlines
5h 57mORF-BOS
$487
5/12dom
multi-stopUnited Airlines
5h 52mBOS-ORF
5/19dom
multi-stopUnited Airlines
4h 12mORF-BOS
$531

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Flights to Chesapeake

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