Cheap flights To Dover (BOS) from $39

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Cheap Flights to Dover from $39 One Way, $78 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 20 - Wed, May 27
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 20 from Raleigh - Durham Intl. to Logan Intl., returning Wed, May 27, priced at $78 found 2 days ago
Sat, May 23 - Mon, Jun 1
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 23 from Raleigh - Durham Intl. to Logan Intl., returning Mon, Jun 1, priced at $98 found 3 days ago
Sun, May 3 - Sat, May 9
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, May 3 from Raleigh - Durham Intl. to Logan Intl., returning Sat, May 9, priced at $100 found 2 days ago
Thu, Apr 9 - Sun, Apr 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$105 Roundtrip, found 5 days ago
$105
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 9 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Apr 12, priced at $105 found 5 days ago
Mon, May 4 - Wed, May 13
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, May 4 from Raleigh - Durham Intl. to Logan Intl., returning Wed, May 13, priced at $106 found 6 days ago
Thu, Apr 9 - Sun, Apr 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 9 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Apr 12, priced at $109 found 6 days ago
Sat, May 30 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, May 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 6, priced at $117 found 5 days ago
Sat, Apr 4 - Tue, May 5
MCO
Orlando Intl.
BOS
Logan Intl.
$121 Roundtrip, found 16 hours ago
$121
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sat, Apr 4 from Orlando Intl. to Logan Intl., returning Tue, May 5, priced at $121 found 16 hours ago
Sat, Aug 29 - Sat, Sep 5
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Aug 29 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Sep 5, priced at $122 found 2 days ago
Wed, Aug 26 - Wed, Aug 26
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 26, priced at $140 found 2 days ago

Dover Flight Information

Traveling To
Dover
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Breeze Airways
Flight Price
$78
Earliest Departing Flight
Latest Departing Flight

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Dover economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Boxboro Regency
3.0-star property

The Boxboro Regency

May 15 - May 19

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Price was $530, price is now $408 per person
$408
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Apr 24 - Apr 26

2 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,207, price is now $773 per person
$773
per person
found 1 day ago
The Inn at Hastings Park, Relais & Chateaux - Boston
4.0-star property

The Inn at Hastings Park, Relais & Chateaux - Boston

May 15 - May 19

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,515, price is now $1,127 per person
$1,127
per person
found 1 day ago
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See all available trips from Chicago to Dover
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Dover first class flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Parker House
4.5-star property

Omni Parker House

9/10 Wonderful! (3,322 reviews)

Apr 28 - Apr 30

2 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $854, price is now $708 per person
$708
per person
found 1 day ago
The room was very small and the bathroom was smaller. It was fine because it was just one night and in the winter, so we got a great rate. We just kept saying thank goodness we didn't pay the high season rate. Location is amazing!

Reviewed on Mar 4, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Apr 28 - Apr 30

2 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,111, price is now $1,365 per person
$1,365
per person
found 1 day ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

Club Quarters Hotel Faneuil Hall, Boston
4.0-star property

Club Quarters Hotel Faneuil Hall, Boston

9/10 Wonderful! (2,995 reviews)

Apr 28 - Apr 30

2 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $904, price is now $769 per person
$769
per person
found 1 day ago
Staff was great and this is a great location for seeing all the things you want to see in Boston. Issues: Room was hot, elevator was under repair and no fridges in room

Reviewed on Nov 11, 2025

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Dover

Snag some “suite” deals when you add cheap hotel rooms to Dover flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

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Fun for All

While shopping Orbitz sales on Dover flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Dover flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Dover. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

Frequently asked questions

Which airlines fly to Dover?
Look for a flight that suits your schedule among the 20 airlines that run services to and from Portland Intl. Jetport Airport (PWM). The best way to save on ticket fares is to book in advance. Take a look at these reputable domestic air carriers and lock in a great deal today:

  • Delta - 168 flights to Dover per month
  • American Airlines - 136 flights to Dover per month
  • United Airlines - 114 flights to Dover per month

How much is a flight to Dover?
Last week, prices hovered between $78 and $140 for a return fare to Dover. One-way tickets departing from Raleigh (RDU) dipped as low as just $39 over the same period.
How to book the cheapest flight to Dover?
Landing cheap flights to Dover is as easy as booking your ticket with Orbitz. But if you'd like to make sure you're grabbing the best flight deals around, here are a few tips to keep your wallet happy:

  • Taking off from or landing at other airports may help you cut costs. Enter your preferred departure and arrival points. Next, click on the 'Nearby airports' function below the form fields to look through your options.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' option. You'll see the flight deals for the days either side of your chosen departure. Fares often vary depending on what day of the week it is.
  • To refine your results, click on 'Show options.' You can search based on seating class, airlines, and nonstop and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird gets the most rewarding savings, so book as soon as you know your travel dates. The most affordable fares get snapped up fast and prices rise as the departure date nears.
  • Think about bundling your flights, hotels and car rentals into one convenient package deal to save cash.
  • Don't travel during the busy season if possible. By steering clear of summer and school vacations, you can save plenty on your airfare.

What is the best time to book a flight to Dover?
Land a bargain and book your tickets to Dover in January. If you've missed this month, don't stress. February and August often have low airfares available. Just make sure you don't sleep on a sale though — cheap flights pop up and disappear in the click of a mouse!
What day of the week is the cheapest to book a flight to Dover?
Make a booking on a Tuesday, Wednesday or Saturday. Typically, these are the cheapest days of the week to purchase airfares to Dover. The getaway of your dreams starts with a fantastic flight deal!
What is the cheapest day of the week to fly to Dover?
Everybody enjoys a great deal, so think about setting off earlier in the week to nab cheap flights to Dover. Orbitz data from 2020 suggests you can lock in the best deals on flights leaving on Mondays. Tuesdays are the next most affordable day, while Saturdays are the costliest. Many passengers like to travel when the working week is over, so leave those Saturdays for checking in with friends.
What is the cheapest month to fly to Dover?
We won't keep you in suspense — based on Orbitz data, August is generally the most affordable month to fly. Perfect for those who want to sneak in a weekend getaway or just an escape from it all before the weather changes. Be aware that the costliest time to fly is the height of summer, with airfares peaking in June.
Which airlines allow free cancellation?
If you're concerned your travel plans may change, Orbitz will help you find a flexible ticket. All you need to do is choose "Filter by flexible change policies" when searching for your Dover flights. We'll show you airlines that include free cancellation and no change fees — all on top of irresistibly low prices.
What do I need for the flight to Dover?
Flying doesn't have to be a drag. In fact it can be fun with a little pre-planning! Make your flight a total breeze with these practical tips:

  • Your travel documents are the most important things you'll need to take on your flight. To avoid any confusion at the time of check-in, make sure that the name on your ticket corresponds with your government-issued photo ID.
  • Take some activities to keep you busy on your journey to Dover. Books, magazines and electronic gadgets like e-readers and laptops are perfect. Remember to take a water bottle as well. Even on short flights, it's important to stay well-hydrated.
  • Even if you're traveling when it's sweltering outside, take a hoodie or sweater on board with you. Cabins are notorious for getting a bit chilly!

How do I get cheap first-class/business deals to Dover?
There are ways of booking first or business-class fares to Dover that won't burn a hole through your wallet. Find a seat at the front of the plane for less with these handy hints:

  • Flexibility isn't just for the gym. Have some room to move around your travel dates so you can pick up more affordable airfares when a huge sale drops.
  • Budget airlines offer business-class seats at a fraction of the usual cost. Ditch the full-service carriers and look up these cheaper options.
  • Take advantage of your airline's frequent flyer program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction.

What is the best time to go to Dover?
Dover is popular in March, April and July. If you're thinking of visiting during these months, it would be wise to book in advance to ensure you score the greatest deals. Curious to know what summer's like in Dover? Average daily temperatures generally hover between 60 ºF and 75 ºF. Like most of the Northern Hemisphere, summer kicks off June 20 here.

More to Explore

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.