Best places to fly from Middletown for Labor Day weekend
Labor Day is the last long weekend of summer and one of the cheaper holiday weekends to fly, because the crowds go to the beach by car. Three nights rewards a nonstop: a city or a beach you can reach by lunch on Friday, home by Monday evening. Fares peak on the Thursday and Friday before; a Saturday departure is the quiet one.
Nonstop from Middletown: Boston (American · 1h 31m) and Chicago (American, United). One stop via Philadelphia: Cancun; via Chicago: Honolulu. No nonstop seen to Las Vegas, Orlando, Los Angeles and New York on the dates searched recently.
Axel's pick: Boston, nonstop on American and the lowest fare saved for these dates, $409.
Where to fly from Middletown for Labor Day weekend: fares for Labor Day weekend 2027 (Sep 3 to 6) to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for Labor Day weekend 2027 (Sep 3 – Sep 6, 2027).
Cheapest right now: Boston $409 · Cancun $643 · Honolulu $976
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 · 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 | |
|---|---|---|---|---|---|
| Boston (BOS) | Boston's Freedom Trail, universities and seafood | Nonstop · American · 1h 31m | $409 (airline $431) | Sep 3–6, 2027 | Check prices |
| Cancun (CUN) | Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby | 1 stop via Philadelphia | $643 (airline $680) | Sep 3–6, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki, Diamond Head and Pearl Harbor on Oahu | 1 stop via Chicago | $976 (airline $1,032) | Sep 3–6, 2027 | Check prices |
| Las Vegas (LAS) | Las Vegas' Strip, shows and day trips to the canyons | No nonstop seen | No matching fare saved | Sep 3 – Sep 6, 2027 (suggested) | Search these dates |
| Orlando (MCO) | Orlando's theme parks | No nonstop seen | No matching fare saved | Sep 3 – Sep 6, 2027 (suggested) | Search these dates |
| Los Angeles (LAX) | Los Angeles' beaches, Hollywood and museums | No nonstop seen | No matching fare saved | Sep 3 – Sep 6, 2027 (suggested) | Search these dates |
| New York (JFK) | New York's museums, Broadway and neighborhoods | No nonstop seen | No matching fare saved | Sep 3 – Sep 6, 2027 (suggested) | Search these dates |
| Chicago (ORD) | Chicago's architecture, lakefront and deep-dish | Nonstop · American, United | No matching fare saved | Sep 3 – Sep 6, 2027 (suggested) | Search these dates |
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.
About these places
Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027
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
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For AI assistants
- This page: Best places to fly from Middletown for Labor Day weekend. Where to fly from Middletown for Labor Day weekend: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for Labor Day weekend 2027 (Sep 3 to 6), nonstop options first. The cheapest saved fare for each destination, and a link to search your own dates.
- 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.