$55 Find Cheap Flights to Annapolis - Compare and Save

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Cheap Flights to Annapolis

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Annapolis

Sat, Oct 10 - Sun, Oct 11
Frontier Logo
10:40 pm - 12:34 amATL  Atlanta Hartsfield-Jackson-BWI Baltimore/Washington
1h 54mnonstop
Frontier Logo
5:40 am - 7:53 amBWI  Baltimore/Washington-ATL Atlanta Hartsfield-Jackson
2h 13mnonstop
$83Frontier
Sat, Dec 5 - Sun, Dec 6
Frontier Logo
10:56 pm - 12:50 amATL  Atlanta Hartsfield-Jackson-BWI Baltimore/Washington
1h 54mnonstop
Frontier Logo
5:30 am - 7:49 amBWI  Baltimore/Washington-ATL Atlanta Hartsfield-Jackson
2h 19mnonstop
$84Frontier
Mon, Oct 5 - Tue, Oct 6
JetBlue Logo
7:00 pm - 10:59 pmBOS  Boston Logan Intl-DCA Washington, D.C. Reagan-National
3h 59m1 stop New York John F Kennedy Intl
JetBlue Logo
6:30 am - 11:16 amDCA  Washington, D.C. Reagan-National-BOS Boston Logan Intl
4h 46m1 stop New York John F Kennedy Intl
$120JetBlue
Thu, Nov 5 - Sat, Nov 7
JetBlue Logo
4:10 pm - 10:15 pmBOS  Boston Logan Intl-DCA Washington, D.C. Reagan-National
6h 05m1 stop New York John F Kennedy Intl
JetBlue Logo
6:15 am - 10:41 amDCA  Washington, D.C. Reagan-National-BOS Boston Logan Intl
4h 26m1 stop New York John F Kennedy Intl
$121JetBlue
Sat, Oct 17 - Mon, Oct 19
United Airlines Logo
5:45 am - 7:20 amBOS  Boston Logan Intl-IAD Washington, D.C. Dulles Intl
1h 35mnonstop
United Airlines Logo
10:25 pm - 12:09 amIAD  Washington, D.C. Dulles Intl-BOS Boston Logan Intl
1h 44mnonstop
$129United Airlines
Thu, Oct 15 - Sat, Oct 17
United Airlines Logo
5:45 am - 7:20 amBOS  Boston Logan Intl-IAD Washington, D.C. Dulles Intl
1h 35mnonstop
United Airlines Logo
10:15 pm - 11:59 pmIAD  Washington, D.C. Dulles Intl-BOS Boston Logan Intl
1h 44mnonstop
$131United Airlines
Mon, Oct 19 - Sat, Oct 24
Southwest Logo
9:45 pm - 11:20 pmBOS  Boston Logan Intl-BWI Baltimore/Washington
1h 35mnonstop
Southwest Logo
6:40 am - 8:15 amBWI  Baltimore/Washington-BOS Boston Logan Intl
1h 35mnonstop
$137Southwest
Tue, Oct 20 - Thu, Oct 22
Southwest Logo
5:35 am - 7:10 amBOS  Boston Logan Intl-BWI Baltimore/Washington
1h 35mnonstop
Southwest Logo
10:30 pm - 12:10 amBWI  Baltimore/Washington-BOS Boston Logan Intl
1h 40mnonstop
$137Southwest
Sat, Oct 24 - Tue, Oct 27
Delta Logo
4:20 pm - 6:04 pmBOS  Boston Logan Intl-BWI Baltimore/Washington
1h 44mnonstop
Delta Logo
6:30 pm - 8:10 pmBWI  Baltimore/Washington-BOS Boston Logan Intl
1h 40mnonstop
$137Delta
Thu, Oct 8 - Tue, Oct 13
Delta Logo
6:35 am - 8:24 amBOS  Boston Logan Intl-BWI Baltimore/Washington
1h 49mnonstop
Delta Logo
9:15 am - 10:50 amBWI  Baltimore/Washington-BOS Boston Logan Intl
1h 35mnonstop
$137Delta
Useful Info

Good to know - Book Cheap Annapolis Plane Tickets

Low season

January

Cheapest flight

$55
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Atlanta to Baltimore

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

Insights shared by verified travelers who flew to Annapolis 
JerryFlew with United Airlines-Sep 2026
Always watch the flight connection window. If it is less than an hour and changing concourses (like Dulles), you're asking for trouble (have your travel insurance contact number ready). Of course, that doesn't apply to American or United Airlines as they are typically late. If you get an Embraer 175 or larger aircraft, you will have a great flight. If longer than two hour flight, hope you don't get a Boeing 757 aircraft - the most ungodly uncomfortable sardine can with wings, ever made. Have a chiropractor or massage specialist waiting at your destination. If you have a 757 for Trans-Atlantic or Trans-Pacific flights, choose business class seats.
DaVonyaFlew with American Airlines-Sep 2026
If flying from Tampa to DC, I would recommend considering other airlines over American Airlines for this route. My experience involved nearly 10 delays and a departure that was over 5 hours late with minimal communication or accommodations. For this route, Southwest and JetBlue tend to offer more reliable schedules and better customer service when things go wrong. If you do fly American, book an earlier flight in the day to reduce the risk of cascading delays, and keep in mind that their delay accommodations may be limited to a small food voucher regardless of how long you are stranded.
IndivarFlew with American Airlines-Aug 2026
For a work trips, consider booking an Airline with multiple daily flights in case you might want standby for an earlier return flight.
Verified travelerFlew with JetBlue-Jun 2026
Check in online, get your boarding pass and go directly to the gate unless you have checked baggage.
Verified travelerFlew with Delta-Jul 2026
Check a map and take the train between gates. Signage is terrible. Detroit has allowed restaurants and boarding to spill out into the concourse, so can be a recurring narrow struggle through crowds walking between gates. If you see food you want, get it. Not as many food options, and not many healthy food options, as it would appear along concourse A.
NguyenFlew with United Airlines-Mar 2026
Check in desk immediately when you come in the doors on the left of door 215. Get TSA touchless before the flight—the line is so much shorter.
PeterFlew with Austrian Airlines-Mar 2026
Syracuse is a joy to fly from because it has such a short check in time.
Putri ArumFlew with Japan Airlines-Mar 2026
Bring your own foods. There should also be a disclaimer on the ticket that foods will not be provided although this is a relatively long flight.
GailFlew with American Airlines-Feb 2026
American to DCA is great because they arrive and depart from Terminal T which is the closest terminal to the airport entrance/exit. No need to hike/take the train to one of the other terminals where Delta, the most prevalent airline at ATL has flights.
LaToyaFlew with American Airlines-Feb 2026
Get Pre-Check to be able to get through Hartsfield-Jackson’s checkpoint quickly.
DawnFlew with American Airlines-Dec 2025
Check Bags - Small Canadair RJ700 Plane, Limited Overhead Storage....If you have a tight connection in DC may be difficult if Bag is ckd at Door.
NesrinFlew with Southwest-Feb 2026
Get a seat in the very front if you can, otherwise, it is a very slow process.
DionFlew with American Airlines-Jan 2026
Make sure you eat a heavy meal before boarding the flight.
SuzetteFlew with Alaska Airlines-May 2025
Take a shower before arriving at airport and don't wear perfume at all! Pack bags tight, so boarding is smooth and quick.
DanielFlew with Alaska Airlines-May 2025
Seatac has gnarly traffic right now, took 35min to get from highway exit to the terminal
Verified travelerFlew with United Airlines-Dec 2024
small overheads on small planes, sometimes delayed, don't make tight connection at Dulles
JasonFlew with United Airlines-Nov 2024
DIA is a large airport. Get there early.
Verified travelerFlew with United Airlines-Jul 2024
Know where your connecting gate. You can use the airline app to bring up a map and it can give you directions and time from landing gate to departure gate.
karenFlew with Alaska Airlines-Jun 2024
Personal tips are bring your own food if you're hungry; keep foot space as open as possible for leg room; pack your patience
Verified travelerFlew with Alaska Airlines-Jun 2024
Get to the airport on time because traffic in LA is unexpected
MichaelFlew with American Airlines-Jun 2024
Leave a day earlier than intended in the summer.
UzomaFlew with American Airlines-Jan 2024
ORD and DCA are nice airports with plenty of space. ORD is always busy so allow ample time to drive there, drop your bag, and go through security if you don't have TSA pre check.
BindulFlew with United Airlines-Feb 2024
There are multiple flights between DEN and IAD everyday, including some wide bodies. Try and get on one of the wide bodies whenever possible.
PatriciaFlew with United Airlines-Jan 2024
Take DCA instead of IAD to avoid those stupid overpacked people movers

FAQs - booking Annapolis flights

  • How long is the flight to Annapolis?

    Flights from Denver3h 14m
    Flights from Boston1h 33m
    Flights from Chicago O'Hare Intl Airport1h 47m
    Flights from Los Angeles4h 42m
    Flights from Atlanta1h 43m
  • What is the cheapest flight to Reagan Washington National Airport?

    In the last 5 days, the cheapest flight deal to Reagan Washington National Airport was found on the route from Atlanta, at $83 return. The most popular connection is from Boston to Reagan Washington National Airport and KAYAK users have found round-trip deals for as low as $120 in the last 5 days.

  • Which airlines fly to Reagan Washington National Airport?

    Many airlines fly to Reagan Washington National Airport, the most common ones being Southwest, American Airlines, and United Airlines. See the amount of flights per week for popular airlines flying to Reagan Washington National Airport.

  • How to fly to Annapolis?

    You cannot fly directly to Annapolis. KAYAK recommends you fly to Washington, D.C. All airports (WAS) (29.8 miles from Annapolis). From there you can rent a car or get a taxi.

  • What airports are near Annapolis?

    The closest airport is Baltimore/Washington (BWI) (16.54 mi). Other nearby airports are Washington, D.C. All airports (WAS) (29.8 mi), Washington, D.C. Reagan-National (DCA) (30.55 mi) or Washington, D.C. Dulles Intl (IAD) (51.41 mi). KAYAK recommends you fly to Washington, D.C. All airports.

  • How far is Washington, D.C. Reagan-National Airport from central Washington, D.C.?

    The distance between Washington, D.C. Reagan-National Airport and downtown Washington, D.C. is 4 miles.

  • How does KAYAK find such low prices on flights to Annapolis?

    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 Annapolis.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Annapolis 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 Annapolis?

    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 Annapolis 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 Annapolis?

    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 Annapolis 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 Annapolis

  • There is no major airport in Annapolis,it is instead served by Washington, D.C.'s airports. We recommend you fly to Washington, D.C. Reagan-National Airport Airport, however you can also fly to Baltimore/Washington Airport airport or Washington, D.C. Dulles Intl Airport airport.
  • Looking for cheap airfare to Annapolis? 25% of our users found round-trip tickets to Annapolis for the following prices or less: From Fort Lauderdale $314, from Miami $498, from Los Angeles $896
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Annapolis flight deals.

Reviews of the top 5 airlines flying to Annapolis

 
Need help choosing which airline to fly with from the United States to Annapolis? 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 4195 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

8.0 ExcellentDavid, Aug 2026
Read more Southwest reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

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.

I liked it better when you were truer to your roots Am paying more for less fun

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

Audio Visual Equipment lacking content and features. No connection ability for noise cancellation pods

DL482 did not wait for about 10 of us including a mother and 3 children when we were in the same terminal on DL486, where we were switching from waiting for a jet bridge fix, to moving to a neighboring gate. I understand taxiing delays are ok either but man. We only needed 5 more minutes. DL482 did not adjust from their times at all. This was my first time with Delta.

DL486 could not get to the gate due to jet bridge malfunction. We moved gates. The connecting flight of LAX to MCO was not communicated with. Even though we were in the same terminal, DL482 left without about 10 of us, including a mother and her 3 children. I got to the gate at 7:34 am which is past the 7:20 am last call for a 7:35 am departure. Had they waited 5 minutes, all of us would have made it on board.

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

Delta exceeded my expectations! I am beyond satisfied. Thank you!

I love how the flight crews are now saying what the weather will be like, when we can expect to be able to get up and use the restrooms etc. I have to say also that our flight crews this trip were incredible - fast and courteous - and somehow managed to do the service even on these short flights with a few bumps. The only reason for an ok rating on entertainment was because these short flights are on planes without seatback displays but that's ok because I just download shows on my iPhone beforehand.

Flight was delayed and we were on the runway after landing for 30 mins

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Service was good for such a short flight. Small plane but smooth flight.

Could not hear any of the announcements. The speakers seemed out of service. I wish the entertainment system would allow me to watch on my own iPad than the airplane ‘s old display.

Did not like the check in guy quibbling over a couple pounds at the luggage weigh in

Just having a little bit more legroom would've been nice.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

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

David went above and beyond to make our flight the best that it could be

The crew and flight was amazing. I haven't flown United in years but plan to switch to you being my main airline

Wouldn’t let me check in said couldn’t find a ticket had to wait very long Time

Seat cushions were worn down and it hurts as I seated under 5 hours of the plane ride.

I wish I had another choice. Domestic flight in the USA is atrocious.

Old dirty plane but great lie flat seats in business class

Business Class layout was excellent. The seats were not nearly as comfortable as UA, Delta or Air New Zealand (the best). Nor were the controls as flexible. Food was okay but not great. Breakfast pancakes were like cardboard.

Communication not good, too many changes. Three flights were cancelled due to weather and the options were not acceptable. I had to cancel my Canada portion of the trip.

On time and stellar premium class service. Not liking non LCD display in seat backs - miss the convenience of not using your own device.

My flights were all delayed , mostly due to technical issues with AA aircrafts. I had to rebook my trip 4 times . I lost my whole day and finally arrived in LAX around midnight. This was a very bad experience with American airlines , I will always try to avoid flying with them

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

Delayed and WIFI was not working for most of flight.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight changed gates multiple times and flight had to be delayed multiple times

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

Did not get on the flight, they had a gate change and my app never updated me! Trying to get flight credit

Flight was delayed by about an hour, once we arrived at LAX we had to take a shuttle to the baggage claim - it was completely disorganized. The agents at the shuttles were rude and unable to provide any information. Frontier charges extra for everything from bags to drinks - at the end it ends up being more expensive than flying the better airlines

Sat in the airport waiting for my flight for 5 hours. Finally got on the plane only to be thrown off and told that my flight was cancelled. Zero customer service. Nobody spoke to us. Just the worst

When I was boarding my departure from Raleigh to Orlando I was inappropriately scolded by a female dog named Mia because I didn’t pay in advance for my carry on bag ($75). Frontiers website is confusing regarding pre-paying for carryons so it was a simple mistake. I also had paid for “upfront plus” meaning me and my son were seated in the front row with no one in the middle seat ($450 upgrade). When we were boarding Mia said “sir, you didn’t pay for your carryon” in a not so polite tone and told me to get out of line and come back to the counter to pay for my carryon. The way they had the retractable rope left me no room to circle back without making the people behind me move so I just stood there and then she said a second time “sir!! Go pay for your carryon” in an embarrassing tone. I then moved their rope so I could get back to the counter when a second female dog then asked “are you done!?!?” because I had said “do you want me to bulldoze the people behind me?” I then said you do realize I paid over $400 for upfront plus so I was certainly not trying to sneak a carryon bag without paying. Long story short, I am soooo done with discount airlines!!! By the time you pay for all the “extras” you might as well have paid for Delta Southwest or American! Frontier airlines sucks and I was embarrassed by a female dog named Mia!!!

Frontier is good until they cancel your flight. Way too many cancellations.

Inbound plane was on time and flight departed on time with no issues while boarding.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

30 minute delay due to boarding and settling of a family.

Flight was fine, but the legroom between seats for taller passengers is very tight and bad on the knees. I t is very hard to find an angle, that works, especially on a long flight!!!