$57 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 4/24. 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, 0 bags

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Everything you should know

Cheapest round-trip
$126
Typical prices: $436-$269
Frontier
Wed 5/6Wed 5/13
DFW - ORF • 1 stop
Cheapest non-stop
$177
Typical prices: $272-$88
JetBlue
Tue 6/2Wed 6/3
BOS - ORF • Non-stop
Arrival airport
You can't fly directly to Chesapeake. It is served by Norfolk (ORF), located 10.1 miles from Chesapeake.
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We hope you love your trip to Chesapeake!
Flight Deals
Useful Info
Flight Deals

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

Wed, May 6 - Wed, May 13
Frontier Logo
5:48 am - 11:11 am
DFW
-
ORF
28h 23m
1 stop
Frontier Logo
12:06 pm - 4:13 pm
ORF
-
DFW
29h 07m
1 stop
$126Frontier
Wed, May 6 - Wed, May 13
Frontier Logo
10:29 pm - 11:11 am
EWR
-
ORF
12h 42m
1 stop
Frontier Logo
12:06 pm - 1:18 am
ORF
-
EWR
13h 12m
1 stop
$134Frontier
Mon, Apr 27 - Wed, Apr 29
Southwest Logo
3:45 pm - 10:00 pm
BOS
-
ORF
6h 15m
1 stop
Southwest Logo
11:10 am - 3:55 pm
ORF
-
BOS
4h 45m
1 stop
$182Southwest
Fri, Apr 24 - Sun, Apr 26
American Airlines Logo
2:45 pm - 4:20 pm
JFK
-
ORF
1h 35mnonstop
American Airlines Logo
9:05 am - 10:30 am
ORF
-
JFK
1h 25mnonstop
$228American Airlines
Thu, May 7 - Tue, May 12
Delta Logo
9:29 pm - 11:15 pm
JFK
-
ORF
1h 46mnonstop
Delta Logo
12:00 pm - 1:29 pm
ORF
-
JFK
1h 29mnonstop
$229Delta
Sat, Apr 25 - Sun, Apr 26
American Airlines Logo
2:45 pm - 4:20 pm
JFK
-
ORF
1h 35mnonstop
American Airlines Logo
9:05 am - 10:30 am
ORF
-
JFK
1h 25mnonstop
$230American Airlines
Fri, May 8 - Sun, May 10
Delta Logo
9:29 pm - 11:15 pm
JFK
-
ORF
1h 46mnonstop
Delta Logo
7:08 am - 8:30 am
ORF
-
JFK
1h 22mnonstop
$249Delta
Sat, May 9 - Sat, May 23
United Airlines Logo
5:45 pm - 9:04 pm
ORD
-
ORF
2h 19mnonstop
United Airlines Logo
11:29 am - 1:08 pm
ORF
-
ORD
2h 39mnonstop
$297United Airlines
Sat, May 9 - Tue, May 12
United Airlines Logo
6:00 am - 12:04 pm
ORD
-
ORF
5h 04m
1 stop
United Airlines Logo
5:14 pm - 6:45 pm
ORF
-
ORD
2h 31mnonstop
$307United Airlines
Fri, May 1 - Tue, May 5
Southwest Logo
5:05 pm - 10:55 pm
HOU
-
ORF
4h 50m
1 stop
Southwest Logo
4:25 pm - 8:55 pm
ORF
-
HOU
5h 30m
1 stop
$309Southwest
Useful Info

Good to know - Book Cheap Chesapeake Plane Tickets

Low seasonJanuary
Cheapest flight$57
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 1% 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 
LisaFlew with Breeze Airways
JAX
-
ORF
Mar 2026
Get to airport early and be polite to the TSA workers who still aren’t getting paid due to government shutdown.
MarcoFlew with United Airlines
ORD
-
ORF
Dec 2025
United delayed my luggage twice on flight to Europe (first flight was for an important event) I carry 2 days of clothes in my backpack no matter who I'm flying with United especially so. No less than 2 hour layover to decrease possibility of loss/delay of luggage. Second EU trip my luggage was left in Germany even though my layover was just over 1 hour. Select layovers of 2+ hours although Unite will sell flights with 40 minutes layover (nonsense). 1 hour layover was not enough to transfer luggage in FRA. The last scan was 30 minutes after the flight left (SMH).
NemoFlew with American Airlines
CLT
-
ORF
Mar 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.

FAQs - booking Chesapeake flights

  • How long is the flight to Chesapeake?

    Flights from Hartford1h 30m
    Flights from New York1h 33m
    Flights from Providence1h 30m
    Flights from Boston1h 42m
    Flights from Atlanta1h 54m
  • 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 $126 return. The most popular connection is from Boston to Norfolk and KAYAK users have found round-trip deals for as low as $177 in the last 3 days.

  • Which airlines fly to Norfolk?

    Many airlines fly to Norfolk, the most common ones being American Airlines, Delta, and United Airlines. 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 Fort Lauderdale $117, from Miami $315, from Los Angeles $328
  • 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.
8.1
Breeze AirwaysOverall score based on 276 reviews
8.2Comfort
8.7Crew
6.6Food
8.3Boarding
6.6Entertainment
Airline reviews

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

6.0 GoodJames, Feb 2026
RDU - RSW
Read more Breeze Airways reviews

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

Lost my luggage and terrible experience with customer service trying to track it down

10 hour delay with minimal updates. Couldn’t leave terminal and then ended up on redeye with a dirty broken plane. It is literally impossible to reach customer service via gate agent, app, phone, text or email.

I thought that I had pre-purchased carry-on luggage and was surprised when I tried to check in that I did not have it.

Flight departure was 90 min delayed, and the boarding experience was confused, stressful, and generally poor. Additionally, the wifi on the plane was malfunctioning for all but the final 15 min of the flight into ILM.

Great experience and In love flying in and out of Provo airport

You get what you pay for. It’s like a bus but flying. No frills, no snacks. Leg room was fine, boarding was good.

Overall good. Plenty of legroom and fairly comfortable seats. No issues with capacity and the overhead been even though most people brought several carry-ons on. I don’t think Breeze really enforces the pay for a carry-on rule.

Surprised at how much I enjoyed Breeze. Paid for the Nicer upgrade which made it closer in price to a flag ship carrier but with more comfortable seats and much more leg room. Crew was polite and since we brought our food no loss there. Would make the point that the ‘have to pay for a carry-on is BS’. Most people did not and had several. Still was plenty of room in the overheads.

Comfortable seating, adequate space available, nice to have USB port, polite crew.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

Everything you need to know for your flight to Chesapeake