$38 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 5/13. 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 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.

Recent round-trip flight deals to Chesapeake

KAYAK's recommended round-trip deals from the most popular airlines that fly to Chesapeake.
Discover the best prices for you by selecting your travel dates on KAYAK.
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
Find Deal
Fri, Jul 25 - Mon, Jul 28
Allegiant Air Logo
12:50 pm - 2:29 pmBOS-ORF
1h 39mnonstop
Allegiant Air Logo
10:28 am - 12:03 pmORF-BOS
1h 35mnonstop
$75Allegiant Air
Find Deal
Mon, Jun 2 - Fri, Jun 20
American Airlines Logo
9:30 am - 11:00 amJFK-ORF
1h 30mnonstop
American Airlines Logo
6:06 am - 7:26 amORF-JFK
1h 20mnonstop
$159American Airlines
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Mon, Jul 28 - Sat, Aug 9
Delta Logo
8:25 pm - 10:12 pmLGA-ORF
1h 47mnonstop
Delta Logo
8:00 am - 9:25 amORF-LGA
1h 25mnonstop
$159Delta
Find Deal
Mon, Jul 28 - Sat, Aug 9
Delta Logo
3:20 pm - 5:00 pmJFK-ORF
1h 40mnonstop
Delta Logo
4:20 pm - 5:59 pmORF-JFK
1h 39mnonstop
$163Delta
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Thu, May 29 - Tue, Jun 3
United Airlines Logo
10:05 pm - 11:44 pmEWR-ORF
1h 39mnonstop
United Airlines Logo
6:15 am - 7:46 amORF-EWR
1h 31mnonstop
$163United Airlines
Find Deal
Wed, May 28 - Sat, May 31
American Airlines Logo
2:59 pm - 4:30 pmJFK-ORF
1h 31mnonstop
American Airlines Logo
6:06 am - 7:26 amORF-JFK
1h 20mnonstop
$166American Airlines
Find Deal
Mon, Aug 11 - Sat, Aug 16
United Airlines Logo
9:55 pm - 11:36 pmEWR-ORF
1h 41mnonstop
United Airlines Logo
6:00 am - 7:29 amORF-EWR
1h 29mnonstop
$171United Airlines
Find Deal
Wed, Jul 2 - Mon, Jul 7
Southwest Logo
5:15 am - 9:50 amBOS-ORF
4h 35m1 stop
Southwest Logo
8:10 pm - 12:20 amORF-BOS
4h 10m1 stop
$222Southwest
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Sun, Aug 10 - Sun, Aug 17
Southwest Logo
1:25 pm - 9:40 pmATL-ORF
8h 15m2 stops
Southwest Logo
6:20 am - 10:20 amORF-ATL
4h 00m1 stop
$234Southwest
Find Deal
Tue, Aug 26 - Sat, Aug 30
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Good to know - Book Cheap Chesapeake Plane Tickets

Low seasonJanuary
High seasonJune
Cheapest flight$38
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from New York LaGuardia Airport to Norfolk

Flights to Chesapeake: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Chesapeake 
NemoFlew with American AirlinesCLT-ORFMar 2024
Small plane meant no overhead compartment room, so you got a valet tag when boarding and they checked the bag at the gate. I didn't realize until I exited the gate door this meant I was supposed to pick the bag back up immediately upon getting off the plane and I could not go back down the gateway again to retrieve it. But they transferred the bag to the baggage claim area so it all worked out- just a little confusing at first.
Verified travelerFlew with Spirit AirlinesFLL-ORFMar 2024
Make sure you have your boarding passes ready!

FAQs - booking Chesapeake flights

  • How long is the flight to Chesapeake?

    Flights from Chicago2h 24m
    Flights from Hartford1h 28m
    Flights from New York1h 28m
    Flights from Boston1h 38m
    Flights from Atlanta1h 47m
  • What is the cheapest flight to Norfolk?

    In the last 3 days, the cheapest flight deal to Norfolk was found on the route from New York, at $64 return. The most popular connection is from Boston to Norfolk and KAYAK users have found round-trip deals for as low as $64 in the last 3 days.

  • Which airlines fly to Norfolk?

    Many airlines fly to Norfolk, the most common ones being American Airlines, United Airlines, 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 Miami $182, from Boston $255, from Denver $298
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chesapeake flight deals.

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.
8.1
Breeze AirwaysOverall score based on 160 reviews
8.2Comfort
6.6Entertainment
8.8Crew
8.3Boarding
6.7Food
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025PVU - IAD
Read more Breeze Airways reviews

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

My original booking was a nonstop flight. It got changed to a flight with a 6vhour layover that became a 7+ hour lay over. I'll never fly this airline again after this roundtrip is over.

I was surprised at how wonderful it was. The aircraft was clean. The crew was warm and welcoming and as a result the passengers were friendly. One warning the only free thing was water. I kind of liked picking wet hat I was willing to pay for and what I was willing to skip.

The flight wasn’t big on frills, which is fine with me. I flew into Islip MacArthur Airport, which saved me from having to go through LaGuardia to visit friends on Long Island. It was inexpensive and super convenient!

Great experience! This was my first time flying with them and I could not have been happier.

Airplane was newer and very clean, lots of space. Crew was great. There was no food and entertainment but that was expected so not an issue.

I like that the price is right! The airplane is clean and the staff is friendly. We landed safely, so that is always a gold star in my book! Great job!

Purposely delayed the flight by 2 hours and 58 minutes so that they would not have to give me the FAA mandated refund for a delay of 3 hours. Offered flight credit instead. All that is offered on board is water and coffee, everything else costs money. They charge you for carry on and checked bags. Would not fly again.

nice flight. no frills but a 3 hour flight I caught up on my sleep. Stan O

First time flying Breeze, was very impressed. I will use Breeze again.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

A bit rush for transit. Food and entertainment are not available

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Everything you need to know for your flight to Chesapeake

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