BOS
Cheap flights from Boston
Compare fares from Boston to destinations worldwide from airlines and travel agencies, then book directly with the seller.
BOS → CHI
FROM $91 · 1 STOP
Search not showing? Compare fares on our partner Aviasales →
- No booking fees
- Prices updated daily
- Secure partner checkout
Where to fly from Boston
These are the cheapest round trips from Boston found in travelers' recent searches, across 12 destinations. The lowest is Fort Lauderdale at $98 round trip, leaving January 9, 2027. Next come Washington ($130) and Orlando ($160). 8 of these fares are non-stop.
Popular routes from Boston
One-way fares, with month-by-month prices on each route page.
Cheapest round trips from Boston
Lowest round-trip economy fare per adult found in recent searches, in US dollars, checked October 26, 2026. Select a destination to search those dates.
| To | Round trip | Dates | Airline | Stops |
|---|---|---|---|---|
| Fort Lauderdale United States | $98 | January 9, 2027 – January 21, 2027 | Allegiant Air | Non-stop |
| Washington United States | $130 | January 20, 2027 – January 23, 2027 | jetBlue | Non-stop |
| Orlando United States | $160 | December 6, 2026 – December 14, 2026 | Breeze Airways | Non-stop |
| Miami United States | $208 | December 7, 2026 – December 9, 2026 | American Airlines | Non-stop |
| Chicago United States | $210 | December 18, 2026 – December 20, 2026 | Southwest Airlines | Non-stop |
| New York United States | $230 | October 28, 2026 – October 30, 2026 | jetBlue | Non-stop |
| Raleigh United States | $238 | December 10, 2026 – December 28, 2026 | Breeze Airways | Non-stop |
| San Diego United States | $267 | December 22, 2026 – January 8, 2027 | Alaska Airlines | Non-stop |
| San Francisco United States | $268 | December 4, 2026 – December 7, 2026 | jetBlue | 1 stop |
| Nashville United States | $298 | December 30, 2026 – January 4, 2027 | Southwest Airlines | 1 stop |
| Atlanta United States | $303 | December 1, 2026 – January 6, 2027 | Southwest Airlines | 1 stop |
| Phoenix United States | $304 | December 17, 2026 – December 23, 2026 | jetBlue | 1 stop |
Flights from Boston: FAQ
Where can I fly cheaply from Boston?
In our latest data the cheapest round trips from Boston go to Fort Lauderdale, Washington and Orlando, starting at $98. Fares change daily; the list above shows the latest price for each destination.
Are these prices one-way or round trip?
The destinations list shows round-trip fares found in recent searches. The route pages linked from this page show one-way fares. The final price is always confirmed on the airline's or agency's website.
Are there non-stop flights from Boston?
Yes. Non-stop fares from Boston appear in our data to Fort Lauderdale, Washington, Orlando, Miami and Chicago.
Does Flicket sell the tickets?
No. Flicket is a flight search site. We compare fares from airlines and travel agencies through our partner Aviasales, and you book directly with the airline or agency you choose, on their website and under their terms. Flicket adds no fee to the fare.