Cheap flights To Dover (BOS) from $50

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Cheap Flights to Dover from $50 One Way, $100 Round Trip

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

Fri, Oct 17 - Mon, Oct 20
BNA
Nashville Intl.
BOS
Logan Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Oct 17 from Nashville Intl. to Logan Intl., returning Mon, Oct 20, priced at $100 just found
Tue, Sep 2 - Tue, Sep 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Tue, Sep 9, priced at $114 just found
Wed, Sep 3 - Tue, Sep 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$116 Roundtrip, found 14 hours ago
$116
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Logan Intl., returning Tue, Sep 9, priced at $116 found 14 hours ago
Thu, Sep 4 - Wed, Sep 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Wed, Sep 10, priced at $117 found 3 hours ago
Sun, Oct 19 - Thu, Oct 23
BNA
Nashville Intl.
BOS
Logan Intl.
$120 Roundtrip, found 12 hours ago
$120
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Sun, Oct 19 from Nashville Intl. to Logan Intl., returning Thu, Oct 23, priced at $120 found 12 hours ago
Wed, Sep 3 - Tue, Sep 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$126 Roundtrip, found 14 hours ago
$126
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Logan Intl., returning Tue, Sep 9, priced at $126 found 14 hours ago
Wed, Sep 3 - Tue, Sep 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$126 Roundtrip, found 14 hours ago
$126
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Logan Intl., returning Tue, Sep 9, priced at $126 found 14 hours ago
Tue, Sep 2 - Tue, Sep 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$128 Roundtrip, just found
$128
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Tue, Sep 9, priced at $128 just found
Tue, Oct 7 - Tue, Oct 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$131 Roundtrip, found 5 days ago
$131
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Oct 7 from O'Hare Intl. to Logan Intl., returning Tue, Oct 7, priced at $131 found 5 days ago
Thu, Oct 30 - Mon, Nov 3
ORD
O'Hare Intl.
BOS
Logan Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Delta flight, departing Thu, Oct 30 from O'Hare Intl. to Logan Intl., returning Mon, Nov 3, priced at $137 just found

Dover Flight Information

Traveling To
Dover
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Spirit Airlines, JetBlue Airways, Delta, United, American Airlines, Southwest Airlines
Flight Price
$100
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.
Parker Beach Lodge
3.0-star property

Parker Beach Lodge

Sep 22 - Sep 26

4 night stay

Dallas (DFW) to Boston (BOS)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 15 hours ago
YOTEL Boston
4.0-star property

YOTEL Boston

Sep 17 - Sep 23

6 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 15 hours ago
Raffles Boston
5.0-star property

Raffles Boston

Sep 17 - Sep 23

6 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 15 hours ago
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Dover premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston
4.0-star property

YOTEL Boston

8.6/10 Excellent! (2,098 reviews)

Sep 24 - Sep 30

6 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 4 hours ago
The room was clean, had everything we needed and the location was amazing. Excellent food options and so much to walk around and see.

Reviewed on Jul 13, 2025

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (132 reviews)

Sep 24 - Sep 30

6 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 4 hours ago
Excellent services.

Reviewed on Dec 29, 2024

citizenM Boston North Station
4.0-star property

citizenM Boston North Station

9.2/10 Wonderful! (3,586 reviews)

Sep 24 - Sep 30

6 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 4 hours ago
Awesome location, great views from room. Economical

Reviewed on Jul 6, 2025

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

Dover first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Charles Hotel
4.0-star property

The Charles Hotel

9.2/10 Wonderful! (1,007 reviews)

Sep 24 - Sep 28

4 night stay

Detroit (DTW) to Boston (BOS)

United • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Great Cambridge hotel. Close to T stop and great location in Harvard Square. Lobby is a great place to read or get some work done. Rooms very comfortable.

Reviewed on Mar 31, 2025

Sands by the Sea Motel
2.5-star property

Sands by the Sea Motel

8.2/10 Very Good! (306 reviews)

Sep 19 - Sep 27

8 night stay

Dallas (DFW) to Boston (BOS)

Delta • Non-stop • FirstClass

Boston (BOS) to Dallas (DFW)

American Airlines • Non-stop • FirstClass
per person
just found
Lady at checkin was extremely nice. It was clean and bed was good.

Reviewed on Oct 8, 2023

The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,016 reviews)

Sep 24 - Sep 28

4 night stay

Detroit (DTW) to Boston (BOS)

United • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Was hoping for more.

Reviewed on Jul 31, 2025

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See all available trips from Detroit to Dover
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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.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Dover.

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 $100 and $137 for a return fare to Dover. One-way tickets departing from Nashville (BNA) dipped as low as just $50 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.

Nearby

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.