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Westchester County → Chicago

Dec 21, 2026 · return Dec 26, 2026

HPN → ORD1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 – Sat, Dec 26

American Airlines
12:13 pmHPN
2h 46m
Nonstop
1:59 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
7:29 amHPN
2h 55m
Nonstop
9:24 amORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Sat, Dec 26

Delta Air Lines
12:30 pmHPN
7h
DTW · 3h 28m
6:30 pmORD
Delta Air Lines
8:29 amORD
6h 18m
DTW · 3h 9m
3:47 pmHPN

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Make this trip yours

HPN ⇄ ORD

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-26American AirlinesAA3812 / AA4200$455.002026-10-29T01:05:11Z
2026-12-21 → 2026-12-26Delta Air LinesDL4645 + DL1084 / DL3841 + DL4658$442.002026-10-29T01:05:11Z
2026-12-21 → 2026-12-26American AirlinesAA3496 / AA4200$455.002026-10-29T01:05:11Z
2026-12-21 → 2026-12-26American AirlinesAA5431 + AA2509 / AA4200$438.752026-10-29T01:05:11Z
2026-12-21 → 2026-12-26American AirlinesAA5678 + AA2612 / AA4200$438.752026-10-29T01:05:11Z

2026-12-21 → 2026-12-26 · $455.00

  • American Airlines AA3812: HPN 2026-12-21 12:13:00 → ORD 2026-12-21 13:59:00; nonstop; 166 minutes. Local airport times.
  • American Airlines AA4200: ORD 2026-12-26 12:45:00 → HPN 2026-12-26 15:59:00; nonstop; 134 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $442.00

  • Delta Air Lines DL4645 / DL1084: HPN 2026-12-21 12:30:00 → ORD 2026-12-21 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
    • DL4645: HPN 2026-12-21 12:30:00 → DTW 2026-12-21 14:28:00; layover at DTW: 208 minutes.
    • DL1084: DTW 2026-12-21 17:56:00 → ORD 2026-12-21 18:30:00.
  • Delta Air Lines DL3841 / DL4658: ORD 2026-12-26 08:29:00 → HPN 2026-12-26 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
    • DL3841: ORD 2026-12-26 08:29:00 → DTW 2026-12-26 10:52:00; layover at DTW: 189 minutes.
    • DL4658: DTW 2026-12-26 14:01:00 → HPN 2026-12-26 15:47:00.

2026-12-21 → 2026-12-26 · $455.00

  • American Airlines AA3496: HPN 2026-12-21 07:29:00 → ORD 2026-12-21 09:24:00; nonstop; 175 minutes. Local airport times.
  • American Airlines AA4200: ORD 2026-12-26 12:45:00 → HPN 2026-12-26 15:59:00; nonstop; 134 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $438.75

  • American Airlines AA5431 / AA2509: HPN 2026-12-21 10:00:00 → ORD 2026-12-21 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2026-12-21 10:00:00 → CLT 2026-12-21 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2026-12-21 14:45:00 → ORD 2026-12-21 16:00:00.
  • American Airlines AA4200: ORD 2026-12-26 12:45:00 → HPN 2026-12-26 15:59:00; nonstop; 134 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $438.75

  • American Airlines AA5678 / AA2612: HPN 2026-12-21 06:30:00 → ORD 2026-12-21 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2026-12-21 06:30:00 → DCA 2026-12-21 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2026-12-21 11:46:00 → ORD 2026-12-21 13:08:00.
  • American Airlines AA4200: ORD 2026-12-26 12:45:00 → HPN 2026-12-26 15:59:00; nonstop; 134 minutes. Local airport times.

More dates for this route