$68 Find Cheap Flights to Chesapeake - Compare and Save

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 8/28. 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, 0 bags

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Everything you should know

Cheapest round-trip
$137
Typical prices: $256-$379
Frontier
Wed 9/2Sat 9/12
DFW - ORF • 1 stop
Cheapest non-stop
$249
Typical prices: $239-$496
United Airlines
Sat 9/5Thu 9/10
EWR - 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
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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, Sep 2 - Sat, Sep 12
Frontier Logo
10:00 am - 12:25 pm
DFW
-
ORF
25h 25m
1 stop
Frontier Logo
4:45 pm - 7:00 am
ORF
-
DFW
15h 15m
1 stop
$137Frontier
Mon, Aug 31 - Wed, Sep 2
Frontier Logo
6:17 am - 12:25 pm
DFW
-
ORF
29h 08m
1 stop
Frontier Logo
1:20 pm - 10:31 pm
ORF
-
DFW
10h 11m
1 stop
$137Frontier
Thu, Sep 10 - Sat, Sep 12
Multiple Airlines Logo
2:07 pm - 9:06 pm
DFW
-
ORF
5h 59m
1 stop
Multiple Airlines Logo
4:45 pm - 7:00 am
ORF
-
DFW
15h 15m
1 stop
$163Multiple Airlines
Thu, Sep 10 - Tue, Sep 15
Multiple Airlines Logo
2:07 pm - 9:06 pm
DFW
-
ORF
5h 59m
1 stop
Multiple Airlines Logo
1:18 pm - 6:43 pm
ORF
-
DFW
6h 25m
1 stop
$169Multiple Airlines
Sat, Sep 5 - Thu, Sep 10
United Airlines Logo
9:25 pm - 11:02 pm
EWR
-
ORF
1h 37mnonstop
United Airlines Logo
6:02 am - 7:25 am
ORF
-
EWR
1h 23mnonstop
$249United Airlines
Sat, Sep 5 - Tue, Sep 8
United Airlines Logo
9:25 pm - 11:02 pm
EWR
-
ORF
1h 37mnonstop
United Airlines Logo
10:49 am - 12:14 pm
ORF
-
EWR
1h 25mnonstop
$249United Airlines
Wed, Sep 9 - Sat, Sep 12
JetBlue Logo
4:35 pm - 6:23 pm
BOS
-
ORF
1h 48mnonstop
JetBlue Logo
7:27 pm - 9:46 pm
ORF
-
BOS
2h 19mnonstop
$255JetBlue
Sat, Sep 12 - Sat, Sep 19
JetBlue Logo
4:35 pm - 6:23 pm
BOS
-
ORF
1h 48mnonstop
JetBlue Logo
7:27 pm - 9:46 pm
ORF
-
BOS
2h 19mnonstop
$255JetBlue
Sat, Sep 26 - Tue, Sep 29
Delta Logo
3:15 pm - 5:14 pm
BOS
-
ORF
1h 59mnonstop
Delta Logo
11:40 am - 1:37 pm
ORF
-
BOS
1h 57mnonstop
$257Delta
Wed, Sep 23 - Tue, Sep 29
Delta Logo
9:05 am - 10:58 am
BOS
-
ORF
1h 53mnonstop
Delta Logo
11:40 am - 1:37 pm
ORF
-
BOS
1h 57mnonstop
$257Delta
Useful Info

Good to know - Book Cheap Chesapeake Plane Tickets

Low season

January

Cheapest flight

$68
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Dallas 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 Tampa2h 07m
    Flights from Dallas/Fort Worth Airport2h 56m
    Flights from Boston1h 43m
    Flights from New York3h 11m
    Flights from Atlanta1h 35m
  • What is the cheapest flight to Norfolk?

    In the last 5 days, the cheapest flight deal to Norfolk was found on the route from Dallas, at $137 return. The most popular connection is from New York to Norfolk and KAYAK users have found round-trip deals for as low as $170 in the last 5 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 Fort Lauderdale $179, from Miami $205, from Los Angeles $245
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chesapeake flight deals.

Everything you need to know for your flight to Chesapeake