Winter break trips from Charlottesville
One stop via Charlotte: Cancun and Orlando; via Chicago: Honolulu and New York.
Where to go from Charlottesville 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: Orlando $504 · Cancun $571 · New York $607
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 | AA5969 + AA1778 | $335.00 | 2026-10-29T00:55:15Z |
| 2026-11-20 · one way | United Airlines | UA5372 + UA1671 | $350.00 | 2026-10-29T00:55:15Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA5969 + AA1778 / AA792 + AA5862 | $697.60 | 2026-10-29T00:55:15Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA4281 + UA1618 / UA1672 + UA5565 | $724.85 | 2026-10-29T00:55:15Z |
| 2026-11-20 · one way | United Airlines | UA4281 + UA1618 | $350.00 | 2026-10-29T00:55:15Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA5969 + AA1778 / AA792 + AA5862 | $697.60 | 2026-10-29T00:55:15Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA5372 + UA1671 / UA1672 + UA5565 | $724.85 | 2026-10-29T00:55:15Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA4281 + UA1618 / UA1672 + UA5565 | $724.85 | 2026-10-29T00:55:15Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA5372 + UA1671 / UA1672 + UA5565 | $724.85 | 2026-10-29T00:55:15Z |
2026-11-20 · one way · $335.00
- American Airlines AA5969 / AA1778: CHO 2026-11-20 09:00:00 → CUN 2026-11-20 16:10:00; 1 stop(s) via CLT; 430 minutes. Local airport times.
- AA5969: CHO 2026-11-20 09:00:00 → CLT 2026-11-20 10:32:00; layover at CLT: 157 minutes.
- AA1778: CLT 2026-11-20 13:09:00 → CUN 2026-11-20 16:10:00.
2026-11-20 · one way · $350.00
- United Airlines UA5372 / UA1671: CHO 2026-11-20 10:45:00 → CUN 2026-11-20 20:44:00; 1 stop(s) via ORD; 599 minutes. Local airport times.
- UA5372: CHO 2026-11-20 10:45:00 → ORD 2026-11-20 11:59:00; layover at ORD: 227 minutes.
- UA1671: ORD 2026-11-20 15:46:00 → CUN 2026-11-20 20:44:00.
2026-11-20 → 2026-11-23 · $697.60
- American Airlines AA5969 / AA1778: CHO 2026-11-20 09:00:00 → CUN 2026-11-20 16:10:00; 1 stop(s) via CLT; 430 minutes. Local airport times.
- AA5969: CHO 2026-11-20 09:00:00 → CLT 2026-11-20 10:32:00; layover at CLT: 157 minutes.
- AA1778: CLT 2026-11-20 13:09:00 → CUN 2026-11-20 16:10:00.
- American Airlines AA792 / AA5862: CUN 2026-11-23 15:25:00 → CHO 2026-11-23 22:07:00; 1 stop(s) via CLT; 402 minutes. Local airport times.
- AA792: CUN 2026-11-23 15:25:00 → CLT 2026-11-23 18:30:00; layover at CLT: 136 minutes.
- AA5862: CLT 2026-11-23 20:46:00 → CHO 2026-11-23 22:07:00.
2026-11-27 → 2026-12-04 · $724.85
- United Airlines UA4281 / UA1618: CHO 2026-11-27 10:35:00 → CUN 2026-11-27 16:55:00; 1 stop(s) via IAD; 380 minutes. Local airport times.
- UA4281: CHO 2026-11-27 10:35:00 → IAD 2026-11-27 11:31:00; layover at IAD: 90 minutes.
- UA1618: IAD 2026-11-27 13:01:00 → CUN 2026-11-27 16:55:00.
- United Airlines UA1672 / UA5565: CUN 2026-12-04 08:15:00 → CHO 2026-12-04 18:09:00; 1 stop(s) via ORD; 594 minutes. Local airport times.
- UA1672: CUN 2026-12-04 08:15:00 → ORD 2026-12-04 11:11:00; layover at ORD: 234 minutes.
- UA5565: ORD 2026-12-04 15:05:00 → CHO 2026-12-04 18:09:00.
2026-11-20 · one way · $350.00
- United Airlines UA4281 / UA1618: CHO 2026-11-20 10:35:00 → CUN 2026-11-20 16:55:00; 1 stop(s) via IAD; 380 minutes. Local airport times.
- UA4281: CHO 2026-11-20 10:35:00 → IAD 2026-11-20 11:31:00; layover at IAD: 90 minutes.
- UA1618: IAD 2026-11-20 13:01:00 → CUN 2026-11-20 16:55:00.
2026-11-27 → 2026-12-04 · $697.60
- American Airlines AA5969 / AA1778: CHO 2026-11-27 09:00:00 → CUN 2026-11-27 16:10:00; 1 stop(s) via CLT; 430 minutes. Local airport times.
- AA5969: CHO 2026-11-27 09:00:00 → CLT 2026-11-27 10:32:00; layover at CLT: 157 minutes.
- AA1778: CLT 2026-11-27 13:09:00 → CUN 2026-11-27 16:10:00.
- American Airlines AA792 / AA5862: CUN 2026-12-04 15:25:00 → CHO 2026-12-04 22:07:00; 1 stop(s) via CLT; 402 minutes. Local airport times.
- AA792: CUN 2026-12-04 15:25:00 → CLT 2026-12-04 18:30:00; layover at CLT: 136 minutes.
- AA5862: CLT 2026-12-04 20:46:00 → CHO 2026-12-04 22:07:00.
2026-11-27 → 2026-12-04 · $724.85
- United Airlines UA5372 / UA1671: CHO 2026-11-27 10:45:00 → CUN 2026-11-27 20:44:00; 1 stop(s) via ORD; 599 minutes. Local airport times.
- UA5372: CHO 2026-11-27 10:45:00 → ORD 2026-11-27 11:59:00; layover at ORD: 227 minutes.
- UA1671: ORD 2026-11-27 15:46:00 → CUN 2026-11-27 20:44:00.
- United Airlines UA1672 / UA5565: CUN 2026-12-04 08:15:00 → CHO 2026-12-04 18:09:00; 1 stop(s) via ORD; 594 minutes. Local airport times.
- UA1672: CUN 2026-12-04 08:15:00 → ORD 2026-12-04 11:11:00; layover at ORD: 234 minutes.
- UA5565: ORD 2026-12-04 15:05:00 → CHO 2026-12-04 18:09:00.
2026-11-20 → 2026-11-23 · $724.85
- United Airlines UA4281 / UA1618: CHO 2026-11-20 10:35:00 → CUN 2026-11-20 16:55:00; 1 stop(s) via IAD; 380 minutes. Local airport times.
- UA4281: CHO 2026-11-20 10:35:00 → IAD 2026-11-20 11:31:00; layover at IAD: 90 minutes.
- UA1618: IAD 2026-11-20 13:01:00 → CUN 2026-11-20 16:55:00.
- United Airlines UA1672 / UA5565: CUN 2026-11-23 08:15:00 → CHO 2026-11-23 18:09:00; 1 stop(s) via ORD; 594 minutes. Local airport times.
- UA1672: CUN 2026-11-23 08:15:00 → ORD 2026-11-23 11:11:00; layover at ORD: 234 minutes.
- UA5565: ORD 2026-11-23 15:05:00 → CHO 2026-11-23 18:09:00.
2026-11-20 → 2026-11-23 · $724.85
- United Airlines UA5372 / UA1671: CHO 2026-11-20 10:45:00 → CUN 2026-11-20 20:44:00; 1 stop(s) via ORD; 599 minutes. Local airport times.
- UA5372: CHO 2026-11-20 10:45:00 → ORD 2026-11-20 11:59:00; layover at ORD: 227 minutes.
- UA1671: ORD 2026-11-20 15:46:00 → CUN 2026-11-20 20:44:00.
- United Airlines UA1672 / UA5565: CUN 2026-11-23 08:15:00 → CHO 2026-11-23 18:09:00; 1 stop(s) via ORD; 594 minutes. Local airport times.
- UA1672: CUN 2026-11-23 08:15:00 → ORD 2026-11-23 11:11:00; layover at ORD: 234 minutes.
- UA5565: ORD 2026-11-23 15:05:00 → CHO 2026-11-23 18:09:00.
More dates for this route
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- The Northeast: in fall · in summer · for Thanksgiving · for Christmas · for spring break · for 3 days · for 4 days · for a week
- 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 – 29, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Charlottesville
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 | $571 (airline $604) | Dec 19–26, 2026 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | 1 stop via Chicago | from $1,109 (airline $1,170) | Dec 19–26, 2026 | Check prices |
| Orlando (MCO) | Orlando's theme parks | 1 stop via Charlotte | $504 (airline $531) | Dec 19–26, 2026 | Check prices |
| New York (JFK) | New York's holiday lights, windows and shows | 1 stop via Chicago | $607 (airline $639) | 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
Hotel details in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Express Hotel · Adhara Hacienda Cancun · All 172 hotels in Cancun
For AI assistants
- This page: Winter break trips from Charlottesville. Winter break 2026 flights from Charlottesville: 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.