$43 Find Cheap Flights 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 to Chesapeake departing on 7/28. 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
1 adult, Economy

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Cheap Flights to Chesapeake

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

vr, aug. 8 - ma, aug. 11
Allegiant Air Logo
12:46 pm - 2:25 pmBOS-ORF
1h 39mnonstop
Allegiant Air Logo
10:20 am - 11:56 amORF-BOS
1h 36mnonstop
$46Allegiant Air
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vr, aug. 8 - ma, aug. 11
Allegiant Air Logo
12:46 pm - 2:25 pmBOS-ORF
1h 39mnonstop
Allegiant Air Logo
10:20 am - 11:56 amORF-BOS
1h 36mnonstop
$49Allegiant Air
Find Deal
wo, aug. 27 - wo, sep. 3
Southwest Logo
10:50 am - 5:15 pmBOS-ORF
6h 25m1 stop
Southwest Logo
11:45 am - 3:25 pmORF-BOS
3h 40m1 stop
$109Southwest
Find Deal
wo, aug. 27 - wo, sep. 3
Southwest Logo
9:25 am - 5:15 pmBOS-ORF
7h 50m2 stops
Southwest Logo
11:45 am - 5:05 pmORF-BOS
5h 20m1 stop
$114Southwest
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ma, sep. 22 - di, sep. 23
United Airlines Logo
6:30 pm - 9:52 pmORD-ORF
2h 22mnonstop
United Airlines Logo
5:00 pm - 6:25 pmORF-ORD
2h 25mnonstop
$140United Airlines
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di, aug. 12 - ma, aug. 18
United Airlines Logo
3:40 pm - 11:41 pmORD-ORF
7h 01m1 stop
United Airlines Logo
6:20 am - 7:45 amORF-ORD
2h 25mnonstop
$146United Airlines
Find Deal
do, aug. 21 - ma, aug. 25
American Airlines Logo
8:29 pm - 11:59 pmORD-ORF
2h 30mnonstop
American Airlines Logo
6:12 pm - 7:50 pmORF-ORD
2h 38mnonstop
$147American Airlines
Find Deal
do, sep. 11 - di, sep. 16
American Airlines Logo
6:32 am - 2:44 pmIAH-ORF
7h 12m1 stop
American Airlines Logo
3:43 pm - 10:32 pmORF-IAH
7h 49m1 stop
$159American Airlines
Find Deal
do, aug. 7 - ma, aug. 11
Delta Logo
9:10 pm - 11:06 pmJFK-ORF
1h 56mnonstop
Delta Logo
7:00 am - 8:24 amORF-JFK
1h 24mnonstop
$177Delta
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do, aug. 14 - ma, aug. 18
Delta Logo
12:59 pm - 2:27 pmLGA-ORF
1h 28mnonstop
Delta Logo
10:59 am - 12:24 pmORF-LGA
1h 25mnonstop
$177Delta
Find Deal
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Good to know - Book Cheap Chesapeake Plane Tickets

Low seasonJanuary
High seasonJuly
Cheapest flight$43
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Boston to Norfolk

FAQs - booking Chesapeake flights

  • How long is the flight to Chesapeake?

    Flights from Dallas3h 10m
    Flights from Hartford1h 28m
    Flights from New York1h 32m
    Flights from Boston1h 38m
    Flights from Atlanta1h 57m
  • What is the cheapest flight to Norfolk?

    In the last 3 days, the cheapest flight deal to Norfolk was found on the route from Boston, at $46 return. The most popular connection is from New York to Norfolk and KAYAK users have found round-trip deals for as low as $160 in the last 3 days.

  • Which airlines fly to Norfolk?

    Many airlines fly to Norfolk, the most common ones being American Airlines, Southwest, and Delta. See the amount of flights per week for popular airlines flying to Norfolk.

  • How to fly to Chesapeake?

    You cannot fly directly to Chesapeake. KAYAK recommends you fly to Norfolk (ORF) (10.07 miles from Chesapeake). From there you can rent a car or get a taxi.

  • What airports are near Chesapeake?

    The closest airport is Norfolk (ORF) (10.07 mi). Other nearby airports are Newport News Intl (PHF) (27.61 mi), Richmond Byrd Intl (RIC) (76.33 mi) or Pitt-Greenville (PGV) (99.19 mi). KAYAK recommends you fly to Norfolk.

  • How far is Norfolk Airport from central Norfolk?

    There are 6 miles between Norfolk city center and Norfolk Airport.

  • What is the name of Norfolk’s airport?

    All flights to Norfolk land at Norfolk Airport. The airport code is ORF,and it can also be referred to as Norfolk or Norfolk Intl.

  • How does KAYAK find such low prices on flights 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 to Chesapeake.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chesapeake is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chesapeake

  • There is no major airport in Chesapeake. It is instead served by Norfolk Airport.
  • Looking for cheap airfare to Chesapeake? 25% of our users found round-trip tickets to Chesapeake for the following prices or less: From Boston $80, from Los Angeles $208, from Miami $263
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chesapeake flight deals.

Reviews of the top 5 airlines flying to Chesapeake

 
Need help choosing which airline to fly with from the United States 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
SouthwestOverall score based on 4245 reviews
7.6Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

6.0 GoodAnonymous, Jul 2025BDL - MDW
Read more Southwest reviews

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

Head rest did not move, very uncomfortable. Staff was great. There was no entertainment, would be nice not to have to pay for snack.

Worst airline - on our flight down from MCO to EYW, there was a huuuuuge delay. We were supposed to take off 12p and it was pushed back to almost 2:30p. We boarded the plane and then sat on the tarmac forever because we were "over" weight and had to burn fuel. Rather than ask guests to volunteer and leave, they kept us on the plane. Finally a family decided to off board and take their luggage with them. Shortly after, we left the terminal but then the pilot told us we may have to sit at the end of the runway for 15-20mins to burn more fuel. Which we ended up doing and of course it started to rain. We finally took off 2:50p. We were supposed to land 1p and didn't land until 3:45p. Basically had time to scramble off the plane, grab our luggage, request transportation to our hotel, unpack, rinse off and hustle over to our 6:30p dinner ressy. It's a shame Breeze is the only non-stop airline from MCO to EYW. For this, not sure I'd ever go back to EYW - most def will not take Breeze again.

Flight was rescheduled from (originally) early Saturday departure to a late Sunday departure. Then the late Sunday departure was delayed again (weather) and got in very late. We’ve enjoyed Breeze a lot, but this particular experience was a little disappointing.

Breeze was good but the sandiego airport had traffic and waiting 1 hour in the plane till take off

The return flight was soooooo much colder than the departure flight to Connecticut! I appreciated the layover because I didn't have to change planes. The staff and the service were the best! Everyone was so professional and accommodating. Having internet was great, but for the movies the flight offers through the app could be updated. THANKS EVERYONE! I fly BREEZE every opportunity I can get.

The flight was comfortable with the usual slight turbulence. Macadamia Nuts would be great snacks to purchase in flight.

This is one of the worst trips that I have ever had. Ending up with an overnight delay. I’m not happy with the fact that they did not provide and set up the arrangement needed for lodging that we had to do it on our own. I also feel there should’ve been Compensation for food.

Had to approach landing twice which caused concern but probably due to weather

This was my first time flying your airline and it was okay. The people were nice but I am not used to all the add ons and no movies or even water. But I knew it was going to be that way. I think I prefer paying for the extras to be more comfortable.

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Overall it was good. I missed my connection but I was put on another flight.

The attendant were friendly. I suggest you have a medical attendant on board every flight so that in case someone is sick , he/she will help them.

The woman gate agent in Phoenix was none too sympathetic about my check-in process as I am relatively new with using apps. I almost did not get on because she said I did not check-in. I thought I had via Kayak where I purchased a very expensive ticket. Lesson learned but to be told I may not get on as a matter of factly was difficult to hear.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

Boarded plane and then delayed 1.5 hours while on the plane

Survey sent before we actually left. Delay after delay. Now a crew problem.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

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