Westchester County (HPN) to Chicago (ORD) · Dec 30, 2026 · return Dec 31, 2026

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

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Westchester County to Chicago (ORD) flight deals

2026-12-30 → 2026-12-31 · Axel-exclusive $455.00

• American Airlines AA3496: HPN 2026-12-30 07:02:00 → ORD 2026-12-30 09:00:00; nonstop; 178 minutes. Local airport times.
• American Airlines AA4200: ORD 2026-12-31 12:45:00 → HPN 2026-12-31 15:59:00; nonstop; 134 minutes. Local airport times.

2026-12-30 → 2026-12-31 · Axel-exclusive $442.00

• Delta Air Lines DL4645 / DL1084: HPN 2026-12-30 12:30:00 → ORD 2026-12-30 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
  • DL4645: HPN 2026-12-30 12:30:00 → DTW 2026-12-30 14:28:00; layover at DTW: 208 minutes.
  • DL1084: DTW 2026-12-30 17:56:00 → ORD 2026-12-30 18:30:00.
• Delta Air Lines DL3841 / DL4658: ORD 2026-12-31 08:29:00 → HPN 2026-12-31 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
  • DL3841: ORD 2026-12-31 08:29:00 → DTW 2026-12-31 10:52:00; layover at DTW: 189 minutes.
  • DL4658: DTW 2026-12-31 14:01:00 → HPN 2026-12-31 15:47:00.

2026-12-30 → 2026-12-31 · Axel-exclusive $455.00

• American Airlines AA4179: HPN 2026-12-30 17:47:00 → ORD 2026-12-30 19:43:00; nonstop; 176 minutes. Local airport times.
• American Airlines AA4200: ORD 2026-12-31 12:45:00 → HPN 2026-12-31 15:59:00; nonstop; 134 minutes. Local airport times.

2026-12-30 → 2026-12-31 · Axel-exclusive $438.75

• American Airlines AA5431 / AA2509: HPN 2026-12-30 10:00:00 → ORD 2026-12-30 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
  • AA5431: HPN 2026-12-30 10:00:00 → CLT 2026-12-30 12:09:00; layover at CLT: 156 minutes.
  • AA2509: CLT 2026-12-30 14:45:00 → ORD 2026-12-30 16:00:00.
• American Airlines AA4200: ORD 2026-12-31 12:45:00 → HPN 2026-12-31 15:59:00; nonstop; 134 minutes. Local airport times.

2026-12-30 → 2026-12-31 · Axel-exclusive $438.75

• American Airlines AA5678 / AA2612: HPN 2026-12-30 06:30:00 → ORD 2026-12-30 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
  • AA5678: HPN 2026-12-30 06:30:00 → DCA 2026-12-30 08:10:00; layover at DCA: 216 minutes.
  • AA2612: DCA 2026-12-30 11:46:00 → ORD 2026-12-30 13:08:00.
• American Airlines AA4200: ORD 2026-12-31 12:45:00 → HPN 2026-12-31 15:59:00; nonstop; 134 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Westchester County (HPN) to Chicago (ORD) · Dec 30, 2026 · return Dec 31, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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