Winter break trips from Middletown
One stop via Charlotte: Cancun; via Chicago: New York. No nonstop seen to Honolulu and Orlando on the dates searched recently.
Where to go from Middletown over winter break: fares for Christmas week (December 19 to 26) and New Year's week (December 26 to January 2), for warm beaches, ski trips and holiday cities.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for Christmas week (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027).
Cheapest right now: Cancun $471 · New York $695 · Honolulu $1,089
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 | American Airlines | AA5963 + AA1262 | $285.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 · one way | United Airlines | UA4974 + UA1618 | $290.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA1795 + AA1507 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 → 2026-11-23 | United Airlines / American Airlines | UA4974 + UA1618 / AA1192 + AA5217 | $610.00 | 2026-10-29T01:29:03Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA2777 + AA492 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 · one way | American Airlines | AA2777 + AA492 | $285.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 · one way | American Airlines | AA1795 + AA1507 | $285.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 · one way | American Airlines | AA5638 + AA895 | $285.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA5963 + AA1262 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA2777 + AA492 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA5963 + AA1262 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA5638 + AA895 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA1795 + AA1507 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA5638 + AA895 / AA1192 + AA5217 | $605.00 | 2026-10-29T01:29:03Z |
| 2026-11-27 → 2026-12-04 | United Airlines / American Airlines | UA4974 + UA1618 / AA1192 + AA5217 | $611.00 | 2026-10-29T01:29:03Z |
2026-11-20 · one way · $285.00
- American Airlines AA5963 / AA1262: MDT 2026-11-20 06:08:00 → CUN 2026-11-20 12:44:00; 1 stop(s) via PHL; 396 minutes. Local airport times.
- AA5963: MDT 2026-11-20 06:08:00 → PHL 2026-11-20 07:12:00; layover at PHL: 88 minutes.
- AA1262: PHL 2026-11-20 08:40:00 → CUN 2026-11-20 12:44:00.
2026-11-20 · one way · $290.00
- United Airlines UA4974 / UA1618: MDT 2026-11-20 10:30:00 → CUN 2026-11-20 16:55:00; 1 stop(s) via IAD; 385 minutes. Local airport times.
- UA4974: MDT 2026-11-20 10:30:00 → IAD 2026-11-20 11:30:00; layover at IAD: 91 minutes.
- UA1618: IAD 2026-11-20 13:01:00 → CUN 2026-11-20 16:55:00.
2026-11-20 → 2026-11-23 · $605.00
- American Airlines AA1795 / AA1507: MDT 2026-11-20 07:08:00 → CUN 2026-11-20 17:35:00; 1 stop(s) via DFW; 627 minutes. Local airport times.
- AA1795: MDT 2026-11-20 07:08:00 → DFW 2026-11-20 10:08:00; layover at DFW: 220 minutes.
- AA1507: DFW 2026-11-20 13:48:00 → CUN 2026-11-20 17:35:00.
- American Airlines AA1192 / AA5217: CUN 2026-11-23 17:13:00 → MDT 2026-11-24 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-11-23 22:31:00 → MDT 2026-11-24 00:12:00.
2026-11-20 → 2026-11-23 · $610.00
- United Airlines UA4974 / UA1618: MDT 2026-11-20 10:30:00 → CUN 2026-11-20 16:55:00; 1 stop(s) via IAD; 385 minutes. Local airport times.
- UA4974: MDT 2026-11-20 10:30:00 → IAD 2026-11-20 11:30:00; layover at IAD: 91 minutes.
- UA1618: IAD 2026-11-20 13:01:00 → CUN 2026-11-20 16:55:00.
- American Airlines AA1192 / AA5217: CUN 2026-11-23 17:13:00 → MDT 2026-11-24 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-11-23 22:31:00 → MDT 2026-11-24 00:12:00.
2026-11-27 → 2026-12-04 · $605.00
- American Airlines AA2777 / AA492: MDT 2026-11-27 07:02:00 → CUN 2026-11-27 15:09:00; 1 stop(s) via ORD; 487 minutes. Local airport times.
- AA2777: MDT 2026-11-27 07:02:00 → ORD 2026-11-27 08:30:00; layover at ORD: 90 minutes.
- AA492: ORD 2026-11-27 10:00:00 → CUN 2026-11-27 15:09:00.
- American Airlines AA1192 / AA5217: CUN 2026-12-04 17:13:00 → MDT 2026-12-05 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-12-04 22:31:00 → MDT 2026-12-05 00:12:00.
2026-11-20 · one way · $285.00
- American Airlines AA2777 / AA492: MDT 2026-11-20 07:02:00 → CUN 2026-11-20 15:09:00; 1 stop(s) via ORD; 487 minutes. Local airport times.
- AA2777: MDT 2026-11-20 07:02:00 → ORD 2026-11-20 08:30:00; layover at ORD: 90 minutes.
- AA492: ORD 2026-11-20 10:00:00 → CUN 2026-11-20 15:09:00.
2026-11-20 · one way · $285.00
- American Airlines AA1795 / AA1507: MDT 2026-11-20 07:08:00 → CUN 2026-11-20 17:35:00; 1 stop(s) via DFW; 627 minutes. Local airport times.
- AA1795: MDT 2026-11-20 07:08:00 → DFW 2026-11-20 10:08:00; layover at DFW: 220 minutes.
- AA1507: DFW 2026-11-20 13:48:00 → CUN 2026-11-20 17:35:00.
2026-11-20 · one way · $285.00
- American Airlines AA5638 / AA895: MDT 2026-11-20 05:00:00 → CUN 2026-11-20 12:29:00; 1 stop(s) via CLT; 449 minutes. Local airport times.
- AA5638: MDT 2026-11-20 05:00:00 → CLT 2026-11-20 06:47:00; layover at CLT: 153 minutes.
- AA895: CLT 2026-11-20 09:20:00 → CUN 2026-11-20 12:29:00.
2026-11-20 → 2026-11-23 · $605.00
- American Airlines AA5963 / AA1262: MDT 2026-11-20 06:08:00 → CUN 2026-11-20 12:44:00; 1 stop(s) via PHL; 396 minutes. Local airport times.
- AA5963: MDT 2026-11-20 06:08:00 → PHL 2026-11-20 07:12:00; layover at PHL: 88 minutes.
- AA1262: PHL 2026-11-20 08:40:00 → CUN 2026-11-20 12:44:00.
- American Airlines AA1192 / AA5217: CUN 2026-11-23 17:13:00 → MDT 2026-11-24 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-11-23 22:31:00 → MDT 2026-11-24 00:12:00.
2026-11-20 → 2026-11-23 · $605.00
- American Airlines AA2777 / AA492: MDT 2026-11-20 07:02:00 → CUN 2026-11-20 15:09:00; 1 stop(s) via ORD; 487 minutes. Local airport times.
- AA2777: MDT 2026-11-20 07:02:00 → ORD 2026-11-20 08:30:00; layover at ORD: 90 minutes.
- AA492: ORD 2026-11-20 10:00:00 → CUN 2026-11-20 15:09:00.
- American Airlines AA1192 / AA5217: CUN 2026-11-23 17:13:00 → MDT 2026-11-24 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-11-23 22:31:00 → MDT 2026-11-24 00:12:00.
2026-11-27 → 2026-12-04 · $605.00
- American Airlines AA5963 / AA1262: MDT 2026-11-27 06:08:00 → CUN 2026-11-27 12:44:00; 1 stop(s) via PHL; 396 minutes. Local airport times.
- AA5963: MDT 2026-11-27 06:08:00 → PHL 2026-11-27 07:12:00; layover at PHL: 88 minutes.
- AA1262: PHL 2026-11-27 08:40:00 → CUN 2026-11-27 12:44:00.
- American Airlines AA1192 / AA5217: CUN 2026-12-04 17:13:00 → MDT 2026-12-05 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-12-04 22:31:00 → MDT 2026-12-05 00:12:00.
2026-11-20 → 2026-11-23 · $605.00
- American Airlines AA5638 / AA895: MDT 2026-11-20 05:00:00 → CUN 2026-11-20 12:29:00; 1 stop(s) via CLT; 449 minutes. Local airport times.
- AA5638: MDT 2026-11-20 05:00:00 → CLT 2026-11-20 06:47:00; layover at CLT: 153 minutes.
- AA895: CLT 2026-11-20 09:20:00 → CUN 2026-11-20 12:29:00.
- American Airlines AA1192 / AA5217: CUN 2026-11-23 17:13:00 → MDT 2026-11-24 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-11-23 22:31:00 → MDT 2026-11-24 00:12:00.
2026-11-27 → 2026-12-04 · $605.00
- American Airlines AA1795 / AA1507: MDT 2026-11-27 07:08:00 → CUN 2026-11-27 17:35:00; 1 stop(s) via DFW; 627 minutes. Local airport times.
- AA1795: MDT 2026-11-27 07:08:00 → DFW 2026-11-27 10:08:00; layover at DFW: 220 minutes.
- AA1507: DFW 2026-11-27 13:48:00 → CUN 2026-11-27 17:35:00.
- American Airlines AA1192 / AA5217: CUN 2026-12-04 17:13:00 → MDT 2026-12-05 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-12-04 22:31:00 → MDT 2026-12-05 00:12:00.
2026-11-27 → 2026-12-04 · $605.00
- American Airlines AA5638 / AA895: MDT 2026-11-27 05:00:00 → CUN 2026-11-27 12:29:00; 1 stop(s) via CLT; 449 minutes. Local airport times.
- AA5638: MDT 2026-11-27 05:00:00 → CLT 2026-11-27 06:47:00; layover at CLT: 153 minutes.
- AA895: CLT 2026-11-27 09:20:00 → CUN 2026-11-27 12:29:00.
- American Airlines AA1192 / AA5217: CUN 2026-12-04 17:13:00 → MDT 2026-12-05 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-12-04 22:31:00 → MDT 2026-12-05 00:12:00.
2026-11-27 → 2026-12-04 · $611.00
- United Airlines UA4974 / UA1618: MDT 2026-11-27 10:30:00 → CUN 2026-11-27 16:55:00; 1 stop(s) via IAD; 385 minutes. Local airport times.
- UA4974: MDT 2026-11-27 10:30:00 → IAD 2026-11-27 11:30:00; layover at IAD: 91 minutes.
- UA1618: IAD 2026-11-27 13:01:00 → CUN 2026-11-27 16:55:00.
- American Airlines AA1192 / AA5217: CUN 2026-12-04 17:13:00 → MDT 2026-12-05 00:12:00; 1 stop(s) via CLT; 419 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 137 minutes.
- AA5217: CLT 2026-12-04 22:31:00 → MDT 2026-12-05 00:12:00.
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- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Middletown
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | 1 stop via Charlotte | $471 (airline $496) | Dec 19–26, 2026 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | No nonstop seen | $1,089 (airline $1,150) | Dec 19–26, 2026 | Check prices |
| Orlando (MCO) | Orlando's theme parks | No nonstop seen | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| New York (JFK) | New York's holiday lights, windows and shows | 1 stop via Chicago | $695 (airline $735) | Dec 19–26, 2026 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
Hotels in Cancun with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room
Hotels with an Axel review in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Hacienda Cancun · Akuazul Resorts Adults Only · All 160 reviewed hotels in Cancun
For AI assistants
- This page: Winter break trips from Middletown. Winter break 2026 flights from Middletown: beaches, ski towns and cities, with fares for Christmas week and New Year's week.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.