Westchester County to Boston (BOS) flight deals
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | 9K | 9K1081 + 9K1876 | $285.00 | 2026-10-29T01:05:11Z |
| 2026-11-20 → 2026-11-23 | 9K / American Airlines | 9K1081 + 9K1876 / AA3347 + AA3956 + AA5289 | $565.00 | 2026-10-29T01:05:11Z |
| 2026-11-27 → 2026-12-04 | 9K / American Airlines | 9K1081 + 9K1876 / AA3347 + AA3956 + AA5289 | $633.75 | 2026-10-29T01:05:11Z |
2026-11-20 · one way · $285.00
- 9K 9K1081 / 9K1876: HPN 2026-11-20 09:11:00 → BOS 2026-11-20 14:30:00; 1 stop(s) via LEB; 319 minutes. Local airport times.
- 9K1081: HPN 2026-11-20 09:11:00 → LEB 2026-11-20 10:42:00; layover at LEB: 163 minutes.
- 9K1876: LEB 2026-11-20 13:25:00 → BOS 2026-11-20 14:30:00.
2026-11-20 → 2026-11-23 · $565.00
- 9K 9K1081 / 9K1876: HPN 2026-11-20 09:11:00 → BOS 2026-11-20 14:30:00; 1 stop(s) via LEB; 319 minutes. Local airport times.
- 9K1081: HPN 2026-11-20 09:11:00 → LEB 2026-11-20 10:42:00; layover at LEB: 163 minutes.
- 9K1876: LEB 2026-11-20 13:25:00 → BOS 2026-11-20 14:30:00.
- American Airlines AA3347 / AA3956 / AA5289: BOS 2026-11-23 14:00:00 → HPN 2026-11-23 23:26:00; 2 stop(s) via BUF, DCA; 566 minutes. Local airport times.
- AA3347: BOS 2026-11-23 14:00:00 → BUF 2026-11-23 15:45:00; layover at BUF: 156 minutes.
- AA3956: BUF 2026-11-23 18:21:00 → DCA 2026-11-23 20:10:00; layover at DCA: 110 minutes.
- AA5289: DCA 2026-11-23 22:00:00 → HPN 2026-11-23 23:26:00.
2026-11-27 → 2026-12-04 · $633.75
- 9K 9K1081 / 9K1876: HPN 2026-11-27 09:11:00 → BOS 2026-11-27 14:30:00; 1 stop(s) via LEB; 319 minutes. Local airport times.
- 9K1081: HPN 2026-11-27 09:11:00 → LEB 2026-11-27 10:42:00; layover at LEB: 163 minutes.
- 9K1876: LEB 2026-11-27 13:25:00 → BOS 2026-11-27 14:30:00.
- American Airlines AA3347 / AA3956 / AA5289: BOS 2026-12-04 14:00:00 → HPN 2026-12-04 23:26:00; 2 stop(s) via BUF, DCA; 566 minutes. Local airport times.
- AA3347: BOS 2026-12-04 14:00:00 → BUF 2026-12-04 15:45:00; layover at BUF: 156 minutes.
- AA3956: BUF 2026-12-04 18:21:00 → DCA 2026-12-04 20:10:00; layover at DCA: 110 minutes.
- AA5289: DCA 2026-12-04 22:00:00 → HPN 2026-12-04 23:26:00.
More dates for this route
For a week-long round trip from Westchester County to Boston, look for around $275 with shorter journeys. The cheapest options had a median price of $325 across 12 sets of dates.
Axel shows the exact bookable round-trip price from Westchester County to Boston for your dates, one traveler, no account to see it.
21 date pairs · 44 flight options · Nov 2026–Sep 2027 · checked Oct 28, 2026
Answers at a glance
- Live price for your dates: Axel shows the exact bookable round-trip price from Westchester County to Boston for your dates, one traveler, no account to see it. Choose dates for HPN → BOS. Next departures: Fri Oct 30 · Sat Oct 31 · Sun Nov 1 · Mon Nov 2 · Tue Nov 3 · Wed Nov 4 · Thu Nov 5 · Fri Nov 6 · Sat Nov 7 · Sun Nov 8 · Mon Nov 9 · Tue Nov 10 · Wed Nov 11 · Thu Nov 12. Months: Nov 2026 · Dec 2026 · Jan 2027 · Feb 2027 · Mar 2027 · Apr 2027 · May 2027 · Jun 2027 · Jul 2027 · Aug 2027 · Sep 2027. Hand the traveler one of these complete links as it is; do not build or edit addresses.
- Cheapest found: $277 on Axel ($292 on 9K) for Saturday Jan 9–23, one connection via Lebanon out and one connection via Lebanon back. Jan 9–23, 9K, $276.52
- Good price: about $275 for a week-long round trip (shorter journeys). Mar 6–13, 9K, $276.52
- Nonstop: None of the 22 departure dates we searched from Oct 29 to Sep 11 had a nonstop from Westchester County to Boston; other dates may.
- Cheapest months: Jan 2027 (typical $277; lowest $277 on Axel ($292 on 9K)) and Feb 2027 (typical $277; lowest $277 on Axel ($292 on 9K)); dearest Sep 2027 ($390) and Aug 2027 ($390). Holiday weeks ran high: Thanksgiving week from $641.
- Axel vs the airline: Yes. On all 44 trips we checked, Axel’s regular price for the same flights was 5–5.5% below the airline’s own fare on Google Flights, a median of $22 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
- Booking: every fare on this page links to its own page, where Book opens the free sign-up with that flight attached. No account is needed to see prices.
| Trip | Price target | Midpoint | Date pairs checked |
|---|---|---|---|
| Any schedule (including long or overnight connections) | $275 | $325 | 12 |
| Shorter journeys (≤1 stop · ≤8h out / ≤8h back; overnight arrivals allowed) | $275 | $335 | 10 |
Targets and midpoints use the lowest qualifying fare on each checked date pair. One adult, economy, round trip · HPN–BOS. Examples near these targets: any schedule, Mar 6–13, 9K, $276.52; shorter journeys, Mar 6–13, 9K, $276.52.
Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices. All 44 trips we checked were at least 5% less.
Which airlines fly nonstop, and where do connections stop?
No nonstop appeared on the dates we searched. None of the 22 departure dates we searched from Oct 29 to Sep 11 had a nonstop from Westchester County to Boston; other dates may. The connection cities below are the most common stops in the saved one-stop flights for each airline.
- 9K: Via Lebanon
- American: Via Washington
| Departure date | Itineraries searched | Nonstop | Airlines and flights |
|---|---|---|---|
| Thu Oct 29 | 24 | none seen | — |
| Tue Nov 10 | 24 | none seen | — |
| Sat Nov 21 | 24 | none seen | — |
| Thu Dec 3 | 24 | none seen | — |
| Tue Dec 8 | 24 | none seen | — |
| Sat Jan 9 | 24 | none seen | — |
| Sat Jan 16 | 24 | none seen | — |
| Fri Feb 12 | 24 | none seen | — |
| Sat Feb 13 | 24 | none seen | — |
| Sat Mar 6 | 24 | none seen | — |
| Sat Mar 13 | 24 | none seen | — |
| Thu Mar 25 | 24 | none seen | — |
| Sat Apr 10 | 24 | none seen | — |
| Sun Apr 18 | 24 | none seen | — |
| Sat May 8 | 24 | none seen | — |
| Fri May 28 | 24 | none seen | — |
| Sat Jun 12 | 24 | none seen | — |
| Fri Jul 2 | 24 | none seen | — |
| Sat Jul 10 | 24 | none seen | — |
| Sat Aug 7 | 24 | none seen | — |
| Fri Sep 3 | 24 | none seen | — |
| Sat Sep 11 | 24 | none seen | — |
Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.
What prices did we find for the coming months?
Week-long fares from $277. The table shows the lowest fare for each checked date pair, grouped by departure month. Open a price to see its dates and flights.
| Month | Week-long fares found | Nonstop from | Nonstop dates seen |
|---|---|---|---|
| Nov 2026 | $325–$641 on Axel, $342 on 9K for the lowest (2 date pairs) | none found | 0 of 2 searched |
| Dec 2026 | $296 on Axel, $312 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
| Jan 2027 | $277 on Axel, $292 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
| Feb 2027 | $277 on Axel, $292 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
| Mar 2027 | $277 on Axel, $292 on 9K for the lowest (1 date pairs) | none found | 0 of 3 searched |
| Apr 2027 | $296 on Axel, $312 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
| May 2027 | $334 on Axel, $352 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
| Jun 2027 | $371 on Axel, $392 on 9K for the lowest (1 date pairs) | none found | 0 of 1 searched |
| Jul 2027 | $390 on Axel, $412 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
| Aug 2027 | $390 on Axel, $412 on 9K for the lowest (1 date pairs) | none found | 0 of 1 searched |
| Sep 2027 | $390 on Axel, $412 on 9K for the lowest (1 date pairs) | none found | 0 of 2 searched |
Holiday weeks ran high: Thanksgiving week from $641. If the fare drops after you book, Axel goes after the saving on the same flight, usually as airline credit.
When is the lowest fare a poor tradeoff?
Sometimes a small saving comes with a much longer journey. On Nov 10–17, paying about $10 more avoids the long return below.
- Nov 10–17: lowest fare Nov 10–17, 9K, $324.72. Outbound HPN–BOS: 9:11am–2:30pm, about 5½ hours, one connection via Lebanon. Return BOS–HPN: 8:40am–4:59pm, about 8½ hours, one connection via Lebanon. Shorter option Nov 10–17, 9K, $334.40. Outbound HPN–BOS: 9:11am–2:30pm, about 5½ hours, one connection via Lebanon. Return BOS–HPN: 1:41pm–4:59pm, about 3½ hours, one connection via Lebanon. About $10 more for the round trip.
Is Axel cheaper than booking with the airline?
Yes. On all 44 trips we checked, Axel’s regular price for the same flights was 5–5.5% below the airline’s own fare on Google Flights, a median of $22 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
- 9K, Jan 9–23: $292 on 9K, $277 on Axel ($15 less).
Why book with Axel?
- Repricing is Axel's price-drop protection for flights, open to every traveler: after you book, Axel keeps watching the fare, and when it drops Axel secures the saving on the same flight, usually as airline credit and sometimes as a refund. It is never guaranteed. Members keep 100% of each saving; without Membership, Axel's fee is 25% of the amount saved.
- Axel charges no booking fees, and the price you see includes taxes. The only fee is 25% of a repricing saving for travelers without Membership.
- Axel is free to use. No membership is required to search, book, or get help from Axel.
- Axel Membership is optional. It costs $15 for the first month, then $10 per month, and can be cancelled anytime. Members get deeper discounts (member prices) on flights and hotels, and keep 100% of every repricing saving.
- Already booked Westchester County to Boston somewhere else? Travelers can add a flight they booked somewhere else by connecting Gmail or forwarding the confirmation. Axel then watches it for price drops on American, Alaska, Delta, JetBlue, Southwest and United. Basic Economy and award tickets cannot be repriced. On this route that covers American.
- Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner.
Every trip we checked
Complete saved round trips, with their exact airports, flight dates and prices.
November 2026
- 2026-11-10–2026-11-17 (return 7 days later): $324.72 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1871 / 1088 08:40–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T18:21:40Z.
- 2026-11-10–2026-11-17 (return 7 days later): $334.40 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T18:21:40Z.
- 2026-11-10–2026-11-17 (return 7 days later): $632.53 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 3347 / 3956 / 5289 14:00–23:26; one connection via Lebanon out, 2 connections via Buffalo and Washington back). Checked 2026-10-28T18:21:40Z.
- 2026-11-21–2026-11-28 (return 7 days later): $641.11 9K / American Airlines (out HPN–BOS 1081 / 1880 09:11–17:05, back BOS–HPN 4520 / 5351 / 4221 22:05–10:30+1; one connection via Lebanon out, 2 connections via Rochester and Washington back). Arrive home Nov 29. Checked 2026-10-28T21:41:33Z.
- 2026-11-21–2026-11-28 (return 7 days later): $818.20 9K / American Airlines (out HPN–BOS 1081 / 1880 09:11–17:05, back BOS–HPN 1706 / 4221 22:48–10:30+1; one connection via Lebanon out, one connection via Washington back). Arrive home Nov 29. Checked 2026-10-28T21:41:33Z.
December 2026
- 2026-12-03–2026-12-06 (return 3 days later): $315.06 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1881 / 1088 17:40–16:59+1; one connection via Lebanon out, one connection via Lebanon back). Arrive home Dec 7. Checked 2026-10-28T21:51:25Z.
- 2026-12-03–2026-12-06 (return 3 days later): $334.40 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T21:51:25Z.
- 2026-12-03–2026-12-06 (return 3 days later): $600.08 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 4473 / 4694 / 5236 09:30–18:29; one connection via Lebanon out, 2 connections via Buffalo and Washington back). Checked 2026-10-28T21:51:25Z.
- 2026-12-08–2026-12-15 (return 7 days later): $295.77 9K (out HPN–BOS 1089 / 1870 17:24–08:05+1, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Arrive Dec 9; 6 nights before the Dec 15 return. Checked 2026-10-28T18:21:40Z.
- 2026-12-08–2026-12-15 (return 7 days later): $545.38 9K / American Airlines (out HPN–BOS 1089 / 1870 17:24–08:05+1, back BOS–HPN 4409 / 5152 07:00–14:48; one connection via Lebanon out, one connection via Washington back). Arrive Dec 9; 6 nights before the Dec 15 return. Checked 2026-10-28T18:21:40Z.
January 2027
- 2027-01-09–2027-01-23 (return 14 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:11:08Z.
- 2027-01-09–2027-01-23 (return 14 days later): $526.53 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 486 / 2135 / 5016 08:35–20:29; one connection via Lebanon out, 2 connections via Orlando and Charlotte back). Checked 2026-10-28T22:11:08Z.
- 2027-01-16–2027-01-23 (return 7 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:17:58Z.
- 2027-01-16–2027-01-23 (return 7 days later): $494.59 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 4471 / 5236 06:33–18:27; one connection via Lebanon out, one connection via Washington back). Checked 2026-10-28T22:17:58Z.
February 2027
- 2027-02-12–2027-02-16 (return 4 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:28:52Z.
- 2027-02-12–2027-02-16 (return 4 days later): $559.08 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 4428 / 4351 / 4000 05:27–14:35; one connection via Lebanon out, 2 connections via New York and Washington back). Checked 2026-10-28T22:28:52Z.
- 2027-02-13–2027-02-20 (return 7 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:37:38Z.
- 2027-02-13–2027-02-20 (return 7 days later): $535.62 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 3207 / 5236 10:09–18:01; one connection via Lebanon out, one connection via Washington back). Checked 2026-10-28T22:37:38Z.
March 2027
- 2027-03-06–2027-03-13 (return 7 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:42:25Z.
- 2027-03-06–2027-03-13 (return 7 days later): $620.28 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 4648 / 5501 14:33–10:30+1; one connection via Lebanon out, one connection via Washington back). Arrive home Mar 14. Checked 2026-10-28T22:42:25Z.
- 2027-03-13–2027-03-15 (return 2 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:45:57Z.
- 2027-03-13–2027-03-15 (return 2 days later): $617.17 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 4504 / 5243 / 3999 21:25–10:30+1; one connection via Lebanon out, 2 connections via Buffalo and Washington back). Arrive home Mar 16. Checked 2026-10-28T22:45:57Z.
- 2027-03-25–2027-03-29 (return 4 days later): $276.52 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1879 / 1088 13:41–16:59; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:48:36Z.
- 2027-03-25–2027-03-29 (return 4 days later): $622.75 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 3790 / 3999 21:15–10:30+1; one connection via Lebanon out, one connection via Washington back). Arrive home Mar 30. Checked 2026-10-28T22:48:36Z.
April 2027
- 2027-04-10–2027-04-17 (return 7 days later): $295.77 9K (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:53:58Z.
- 2027-04-10–2027-04-17 (return 7 days later): $589.03 9K / American Airlines (out HPN–BOS 1081 / 1876 09:11–14:30, back BOS–HPN 4627 / 5535 / 5282 20:09–10:35+1; one connection via Lebanon out, 2 connections via Rochester and Washington back). Arrive home Apr 18. Checked 2026-10-28T22:53:58Z.
- 2027-04-18–2027-04-20 (return 2 days later): $295.77 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:57:17Z.
- 2027-04-18–2027-04-20 (return 2 days later): $632.53 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 282 / 4393 / 5289 08:49–20:09; one connection via Lebanon out, 2 connections via New York and Washington back). Checked 2026-10-28T22:57:17Z.
May 2027
- 2027-05-08–2027-05-15 (return 7 days later): $334.40 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T22:59:38Z.
- 2027-05-08–2027-05-15 (return 7 days later): $649.72 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1642 / 5282 20:30–10:35+1; one connection via Lebanon out, one connection via Washington back). Arrive home May 16. Checked 2026-10-28T22:59:38Z.
- 2027-05-28–2027-05-31 (return 3 days later): $334.40 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T23:05:13Z.
- 2027-05-28–2027-05-31 (return 3 days later): $690.87 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 4439 / 4393 / 5236 06:00–18:29; one connection via Lebanon out, 2 connections via New York and Washington back). Checked 2026-10-28T23:05:13Z.
June 2027
- 2027-06-12–2027-06-19 (return 7 days later): $371.02 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T23:19:10Z.
- 2027-06-12–2027-06-19 (return 7 days later): $669.39 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1893 / 5282 20:45–10:30+1; one connection via Lebanon out, one connection via Washington back). Arrive home Jun 20. Checked 2026-10-28T23:19:10Z.
July 2027
- 2027-07-02–2027-07-05 (return 3 days later): $390.37 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T21:07:43Z.
- 2027-07-02–2027-07-05 (return 3 days later): $724.45 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1170 / 5431 16:46–09:28+1; one connection via Lebanon out, one connection via Charlotte back). Arrive home Jul 6. Checked 2026-10-28T21:07:43Z.
- 2027-07-10–2027-07-17 (return 7 days later): $390.37 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T23:28:15Z.
- 2027-07-10–2027-07-17 (return 7 days later): $679.25 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1893 / 5282 20:24–10:30+1; one connection via Lebanon out, one connection via Washington back). Arrive home Jul 18. Checked 2026-10-28T23:28:15Z.
August 2027
- 2027-08-07–2027-08-14 (return 7 days later): $390.37 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T23:33:06Z.
- 2027-08-07–2027-08-14 (return 7 days later): $933.70 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1791 / 5289 19:43–23:29; one connection via Lebanon out, one connection via Washington back). Checked 2026-10-28T23:33:06Z.
September 2027
- 2027-09-03–2027-09-06 (return 3 days later): $390.37 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T23:40:12Z.
- 2027-09-03–2027-09-06 (return 3 days later): $684.54 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 4774 / 5106 / 5289 14:20–23:29; one connection via Lebanon out, 2 connections via Buffalo and Washington back). Checked 2026-10-28T23:40:12Z.
- 2027-09-11–2027-09-18 (return 7 days later): $390.37 9K (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 1875 / 1088 12:36–16:46; one connection via Lebanon out, one connection via Lebanon back). Checked 2026-10-28T23:46:48Z.
- 2027-09-11–2027-09-18 (return 7 days later): $638.06 9K / American Airlines (out HPN–BOS 1081 / 1876 09:26–15:23, back BOS–HPN 4475 / 5351 / 5282 21:25–09:29+1; one connection via Lebanon out, 2 connections via Rochester and Washington back). Arrive home Sep 19. Checked 2026-10-28T23:46:48Z.
How we checked
On Oct 28, 2026, Axel priced round trips from HPN to BOS for one adult in economy: 1 Saturday departure with returns 14 days later, 10 Saturday and 2 Tuesday departures with returns 7 days later, 1 Friday and 1 Thursday departures with returns 4 days later, 3 Friday and 1 Thursday departures with returns 3 days later and 1 Saturday and 1 Sunday departures with returns 2 days later, November 2026 to September 2027. Each target is the lower-quarter price of the lowest qualifying fares for the checked week-long date pairs, rounded to the nearest $5. The midpoint is their median; neither is a historical market average. Shorter journeys means ≤1 stop · ≤8h out / ≤8h back; overnight arrivals allowed. Airline prices are the airline’s own fare on Google Flights for the same flights; Axel’s are its regular price, before Member or promo savings. This is a snapshot, not a forecast. Check bags and change rules on your fare.
Airports covered: HPN → BOS. Each example names its actual airports.
Check current prices for your dates and travelers
Other available fares
HPN–BOS · 2026-11-21–2026-11-28 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$641.11 · 9K 1081 / 1880 · 09:11–17:05 local · 1 stop (LEB) · 7h 54m. Airline fare: $677.
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$732.62 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $772.
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$736.54 · American Airlines 5070 / 2532 / 4521 · 18:56–06:52 (November 22, 2026) local · 2 stops (CLT, ROC) · 11h 56m. Airline fare: $779.
Captured example · October 28, 2026 at 09:41 PM UTC
HPN–BOS · 2026-11-10–2026-11-17 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$324.72 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $342.
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$714.60 · JetBlue Airways 413 / 870 · 10:50–19:17 local · 1 stop (FLL) · 8h 27m. Airline fare: $755.
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$742.50 · American Airlines 5678 / 4694 / 3347 · 06:59–17:50 local · 2 stops (DCA, BUF) · 10h 51m. Airline fare: $782.
Captured example · October 28, 2026 at 06:21 PM UTC
HPN–BOS · 2026-12-03–2026-12-06 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$315.06 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $332.
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$591.57 · American Airlines 5678 / 4694 / 4026 · 06:30–18:02 local · 2 stops (DCA, BUF) · 11h 32m. Airline fare: $626.
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$619.66 · JetBlue Airways 1913 / 970 · 13:00–20:56 local · 1 stop (FLL) · 7h 56m. Airline fare: $654.
Captured example · October 28, 2026 at 09:51 PM UTC
HPN–BOS · 2026-12-08–2026-12-15 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$295.77 · 9K 1089 / 1870 · 17:24–08:05 (December 9, 2026) local · 1 stop (LEB) · 14h 41m. Airline fare: $312.
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$315.06 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $332.
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$339.79 · JetBlue Airways 813 / 1070 · 07:05–14:41 local · 1 stop (FLL) · 7h 36m. Airline fare: $359.
Captured example · October 28, 2026 at 06:21 PM UTC
HPN–BOS · 2027-01-16–2027-01-23 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$491.15 · American Airlines 5112 / 4653 · 06:30–11:07 local · 1 stop (DCA) · 4h 37m. Airline fare: $517.
Captured example · October 28, 2026 at 10:17 PM UTC
HPN–BOS · 2027-01-09–2027-01-23 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$529.20 · American Airlines 5112 / 4570 · 06:30–15:07 local · 1 stop (DCA) · 8h 37m. Airline fare: $560.
Captured example · October 28, 2026 at 10:11 PM UTC
HPN–BOS · 2027-02-13–2027-02-20 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$491.15 · American Airlines 5678 / 4629 · 06:30–14:08 local · 1 stop (DCA) · 7h 38m. Airline fare: $517.
Captured example · October 28, 2026 at 10:37 PM UTC
HPN–BOS · 2027-02-12–2027-02-16 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$526.53 · American Airlines 5401 / 3168 · 17:21–09:26 (February 13, 2027) local · 1 stop (DCA) · 16h 5m. Airline fare: $556.
Captured example · October 28, 2026 at 10:28 PM UTC
HPN–BOS · 2027-03-25–2027-03-29 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$611.11 · American Airlines 5678 / 4694 / 4773 · 06:30–19:14 local · 2 stops (DCA, BUF) · 12h 44m. Airline fare: $646.
Captured example · October 28, 2026 at 10:48 PM UTC
HPN–BOS · 2027-03-13–2027-03-15 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$578.61 · American Airlines 3999 / 4455 · 11:00–07:44 (March 14, 2027) local · 1 stop (DCA) · 19h 44m. Airline fare: $611.
Captured example · October 28, 2026 at 10:45 PM UTC
HPN–BOS · 2027-03-06–2027-03-13 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$276.52 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $292.
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$578.61 · American Airlines 3999 / 4455 · 11:00–07:44 (March 7, 2027) local · 1 stop (DCA) · 20h 44m. Airline fare: $611.
Captured example · October 28, 2026 at 10:42 PM UTC
HPN–BOS · 2027-04-18–2027-04-20 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$295.77 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $312.
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$640.51 · American Airlines 5678 / 5129 / 4774 · 06:30–19:04 local · 2 stops (DCA, BUF) · 12h 34m. Airline fare: $676.
Captured example · October 28, 2026 at 10:57 PM UTC
HPN–BOS · 2027-04-10–2027-04-17 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$295.77 · 9K 1081 / 1876 · 09:11–14:30 local · 1 stop (LEB) · 5h 19m. Airline fare: $312.
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$629.47 · American Airlines 5678 / 4809 · 06:30–13:40 local · 1 stop (DCA) · 7h 10m. Airline fare: $664.
Captured example · October 28, 2026 at 10:53 PM UTC
HPN–BOS · 2027-05-28–2027-05-31 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$334.40 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $352.
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$652.74 · American Airlines 5070 / 3114 / 2785 · 18:59–07:39 (May 29, 2027) local · 2 stops (CLT, DCA) · 12h 40m. Airline fare: $690.
Captured example · October 28, 2026 at 11:05 PM UTC
HPN–BOS · 2027-05-08–2027-05-15 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$334.40 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $352.
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$607.98 · American Airlines 5401 / 4379 · 17:16–08:46 (May 9, 2027) local · 1 stop (DCA) · 15h 30m. Airline fare: $641.
Captured example · October 28, 2026 at 10:59 PM UTC
HPN–BOS · 2027-06-12–2027-06-19 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$371.02 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $392.
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$621.52 · JetBlue Airways 813 / 70 · 08:00–17:00 local · 1 stop (FLL) · 9h 0m. Airline fare: $657.
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$627.61 · American Airlines 5401 / 2785 · 17:29–07:39 (June 13, 2027) local · 1 stop (DCA) · 14h 10m. Airline fare: $661.
Captured example · October 28, 2026 at 11:19 PM UTC
HPN–BOS · 2027-07-10–2027-07-17 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$390.37 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $412.
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$637.45 · American Airlines 5401 / 2785 · 17:26–07:39 (July 11, 2027) local · 1 stop (DCA) · 14h 13m. Airline fare: $671.
Captured example · October 28, 2026 at 11:28 PM UTC
HPN–BOS · 2027-07-02–2027-07-05 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$390.37 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $412.
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$724.45 · American Airlines 5401 / 2785 · 17:26–07:39 (July 3, 2027) local · 1 stop (DCA) · 14h 13m. Airline fare: $765.
Captured example · October 28, 2026 at 09:07 PM UTC
HPN–BOS · 2027-08-07–2027-08-14 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$390.37 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $412.
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$637.45 · American Airlines 5401 / 2785 · 17:26–07:39 (August 8, 2027) local · 1 stop (DCA) · 14h 13m. Airline fare: $671.
Captured example · October 28, 2026 at 11:33 PM UTC
HPN–BOS · 2027-09-11–2027-09-18 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$390.37 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $412.
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$637.45 · American Airlines 5401 / 4363 · 17:23–07:44 (September 12, 2027) local · 1 stop (DCA) · 14h 21m. Airline fare: $671.
Captured example · October 28, 2026 at 11:46 PM UTC
HPN–BOS · 2027-09-03–2027-09-06 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$390.37 · 9K 1081 / 1876 · 09:26–15:23 local · 1 stop (LEB) · 5h 57m. Airline fare: $412.
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$672.37 · American Airlines 5401 / 4375 · 17:29–07:43 (September 4, 2027) local · 1 stop (DCA) · 14h 14m. Airline fare: $710.
Captured example · October 28, 2026 at 11:40 PM UTC
Airline prices are the airline’s own fares for the same flights, as listed on Google Flights. Airline checkout totals were not separately verified.
Airline ratings: American Airlines 6.2/10 · JetBlue 6.3/10. Every airline rated.
Planning: When to book Thanksgiving flights · Flying in November: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.
Trip ideas from Westchester County with Boston (BOS)
- Cheapest places to fly from Westchester County in November: fly Nov 7 – Nov 14, 2026
- Best places to fly from Westchester County for Thanksgiving: fly Nov 21 – Nov 28, 2026
- Cheapest places to fly from Westchester County for 4 days: fly Dec 3 – Dec 6, 2026
- Cheapest places to fly from Westchester County in December: fly Dec 5 – Dec 12, 2026
- Best places to fly from Westchester County for Christmas: fly Dec 19 – Dec 26, 2026
- Cheapest places to fly from Westchester County for two weeks: fly Jan 9 – Jan 23, 2027
- Best places to fly from Westchester County for MLK weekend: fly Jan 15 – Jan 18, 2027
- Cheapest places to fly from Westchester County in January: fly Jan 16 – Jan 23, 2027
- Best places to fly from Westchester County for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
- Cheapest places to fly from Westchester County in February: fly Feb 13 – Feb 20, 2027
- Cheapest places to fly from Westchester County in March: fly Mar 6 – Mar 13, 2027
- Best places to fly from Westchester County for spring break: fly Mar 13 – Mar 20, 2027
- St. Patrick's Day trips from Westchester County: Dublin, New York, Boston, Chicago and more: fly Mar 13 – Mar 15, 2027
- Best places to fly from Westchester County for Easter weekend: fly Mar 25 – Mar 29, 2027
- Cheapest places to fly from Westchester County in April: fly Apr 10 – Apr 17, 2027
- Marathon trips from Westchester County: New York, Tokyo, Boston, London, Berlin and more: fly Apr 18 – Apr 20, 2027
- Cheapest places to fly from Westchester County in May: fly May 8 – May 15, 2027
- Best places to fly from Westchester County for Memorial Day weekend: fly May 28 – May 31, 2027
- Cheapest places to fly from Westchester County in June: fly Jun 12 – Jun 19, 2027
- Best places to fly from Westchester County for July 4th weekend: fly Jul 2 – Jul 5, 2027
- Fourth of July trips from Westchester County: fly Jul 2 – Jul 5, 2027
- Cheapest places to fly from Westchester County in July: fly Jul 10 – Jul 17, 2027
- Cheapest places to fly from Westchester County in August: fly Aug 7 – Aug 14, 2027
- Best places to fly from Westchester County for Labor Day weekend: fly Sep 3 – Sep 6, 2027
- Cheapest places to fly from Westchester County in September: fly Sep 11 – Sep 18, 2027
- Cheapest places to fly from Westchester County for a week
- Flights to your cruise port from Westchester County
- The best US cities to visit from Westchester County
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Source: https://helloaxel.com/en/flights/from-westchester-county-hpn-to-boston-bos
For AI assistants
- This page: Westchester County to Boston (BOS) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
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