$273 Cheap flight deals from Charleston (CRW) to Gloucester (BOS)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Airfares from $273 One Way, $308 Round Trip from Charleston to Gloucester

Prices starting at $308 for return flights and $273 for one-way flights to Gloucester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 29 - Wed, Oct 21
CRW
Charleston
BOS
Boston
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 29 from Charleston to Boston, returning Wed, Oct 21, priced at $308 found 1 day ago
Tue, Sep 29 - Wed, Oct 21
CRW
Charleston
BOS
Boston
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 29 from Charleston to Boston, returning Wed, Oct 21, priced at $308 found 1 day ago
Fri, Sep 11 - Sun, Sep 13
CRW
Charleston
BOS
Boston
$313 Roundtrip, found 12 hours ago
$313
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Fri, Sep 11 from Charleston to Boston, returning Sun, Sep 13, priced at $313 found 12 hours ago
Tue, Sep 29 - Wed, Oct 21
CRW
Charleston
BOS
Boston
$323 Roundtrip, found 1 day ago
$323
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 29 from Charleston to Boston, returning Wed, Oct 21, priced at $323 found 1 day ago
Tue, Sep 29 - Wed, Oct 21
CRW
Charleston
BOS
Boston
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 29 from Charleston to Boston, returning Wed, Oct 21, priced at $353 found 1 day ago

Gloucester economy flight packages

Price found within the past 48 hours. Click for updated prices.
enVision Hotel Boston Everett
2.0-star property

enVision Hotel Boston Everett

8.4/10 Very Good! (1,015 reviews)

Oct 5 - Oct 10

5 night stay

Charleston (CRW) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Price was $1,196, price is now $1,007 per person
$1,007
per person
found 1 day ago
This is uniquely decorated hotel to fit the theme of a warehouse being turned into a hotel. It’s a unique location in the quaint Chelsea neighborhood. We loved the giant Scrabble board in the lobby and the mattresses are very comfortable. However, it’s a very busy loud neighborhood! I recommend ear plugs. When we arrived in the room there were food crumbs on the floor. The shower pressure was non-existent and the tub doesn’t drain properly. We didn’t have the room clean our first two days but did ask for it on the 3rd although it was an afternoon request we were asked to confirm the room number a twice, but still didn’t receive a cleaning. We ran out of toilet paper, Shower gel and towels on our check out day, so I had to go ask for these items, and that was disappointing. If you’re trying to save money as were by going to outskirts of city…don’t! Pay to stay downtown. You’ll save on the Uber/Lyfts which you can add to getting a better hotel in the city limits and walk or trolley to sites and also you may be able to sleep in!

Reviewed on Aug 19, 2026

Arcadian Hotel
3.5-star property

Arcadian Hotel

8.2/10 Very Good! (4,382 reviews)

Oct 5 - Oct 10

5 night stay

Charleston (CRW) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,377, price is now $1,052 per person
$1,052
per person
found 1 day ago
Les points positifs: . Le stationnement intérieur, très pratique car très difficile d’avoir du stationnement à Boston. . Métro en face de l’Hôtel, une fois la voiture au parking, plus besoin de la sortir. Ligne direct pour Fenway (20 min de marche), Back Bay et Centre-Ville. Points négatifs: . Déjeuner très très basic, selon avantage sauver un repas dans le calcul des dépenses

Reviewed on Aug 19, 2026

Hotel AKA Boston Common
4.0-star property

Hotel AKA Boston Common

9/10 Wonderful! (1,732 reviews)

Oct 5 - Oct 10

5 night stay

Charleston (CRW) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,007, price is now $1,676 per person
$1,676
per person
found 1 day ago
Hotel is very nice! Location is great, super walkable. A few things to look out for though: Parking isn’t available at this hotel other than valet and city parking isn’t close by, a good 10 minute walk. We got a knock at the door from cleaning staff trying to come and clean the room at 9 am both days which was way too early. We would’ve appreciated if they waited until at least 10 am.

Reviewed on Aug 19, 2026

Don't see what you're looking for?
See all available trips from Charleston to Gloucester
View all trips

More About Flying To Gloucester from Charleston

Route Information for Flights from Charleston to Gloucester

Origin Airport IATA Code
CRW
Destination Airport IATA Code
BOS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Charleston to Gloucester

Searching for deals for cheap flights from Charleston to Gloucester? Orbitz has your guaranteed low prices and offers cutting-edge mobile tools to make it easy to find bargain air tickets.

Use Orbitz Apps to Find Charleston to Gloucester Flights

Smartphone users can download the Orbitz app for Android and iPhone devices to get information on low fare deals for flights from Charleston to Gloucester anytime. These apps allow users to not only book tickets but check on their flight status and get the details they need to find the right departure gate—right on their mobile device.

Earn Miles on Your Cheap Flight

Orbitz makes it simple to earn points for your frequent flyer program when you book certain flights from Charleston to Gloucester. Just enter the account number associated with your frequent flyer program during the booking process, and your points or miles will be added after you complete your flight.

Orbitz Flight Alerts Keep You Updated

Along with offering bargain prices for Charleston to Gloucester flights, Orbitz also features free flight alerts that inform you of any abrupt changes to your travel itinerary. You can opt to have your alerts sent by email, voice, or text message. Orbitz will even forward the alerts to your contacts, who may need to adjust their plans for picking you up at the terminal.

Get Bargain Fares for Charleston to Gloucester Flights

Orbitz makes it quick and easy to find airfare sales and low fare tickets. Decide which airline and flight times you want or, if your schedule is flexible, choose a range of dates to see the best prices.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.