# Westchester County (HPN) to Chicago (ORD) · Dec 28, 2026 · return Dec 30, 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.

| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
| --- | --- | --- | ---: | --- |
| 2026-12-28 → 2026-12-30 | American Airlines | AA4179 / AA3812 | [Axel-exclusive $455.00](https://helloaxel.com/en/f/start/from/hpn/to/ord/depart/december-28-2026/return/december-30-2026/adults/1/cabin/economy) | 2026-10-29T01:05:11Z |
| 2026-12-28 → 2026-12-30 | Delta Air Lines | DL4645 + DL1084 / DL3841 + DL4658 | [Axel-exclusive $442.00](https://helloaxel.com/en/f/start/from/hpn/to/ord/depart/december-28-2026/return/december-30-2026/adults/1/cabin/economy) | 2026-10-29T01:05:11Z |
| 2026-12-28 → 2026-12-30 | American Airlines | AA3496 / AA3812 | [Axel-exclusive $455.00](https://helloaxel.com/en/f/start/from/hpn/to/ord/depart/december-28-2026/return/december-30-2026/adults/1/cabin/economy) | 2026-10-29T01:05:11Z |
| 2026-12-28 → 2026-12-30 | American Airlines | AA5431 + AA2509 / AA3812 | [Axel-exclusive $438.75](https://helloaxel.com/en/f/start/from/hpn/to/ord/depart/december-28-2026/return/december-30-2026/adults/1/cabin/economy) | 2026-10-29T01:05:11Z |
| 2026-12-28 → 2026-12-30 | American Airlines | AA5678 + AA2612 / AA3812 | [Axel-exclusive $438.75](https://helloaxel.com/en/f/start/from/hpn/to/ord/depart/december-28-2026/return/december-30-2026/adults/1/cabin/economy) | 2026-10-29T01:05:11Z |

[Route overview: Westchester County to Chicago (ORD) flight deals](/en/flights/from-westchester-county-hpn-to-chicago-ord)

### 2026-12-28 → 2026-12-30 · Axel-exclusive $455.00

- American Airlines AA4179: HPN 2026-12-28 17:47:00 → ORD 2026-12-28 19:43:00; nonstop; 176 minutes. Local airport times.
- American Airlines AA3812: ORD 2026-12-30 08:14:00 → HPN 2026-12-30 11:29:00; nonstop; 135 minutes. Local airport times.

### 2026-12-28 → 2026-12-30 · Axel-exclusive $442.00

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

### 2026-12-28 → 2026-12-30 · Axel-exclusive $455.00

- American Airlines AA3496: HPN 2026-12-28 07:02:00 → ORD 2026-12-28 09:00:00; nonstop; 178 minutes. Local airport times.
- American Airlines AA3812: ORD 2026-12-30 08:14:00 → HPN 2026-12-30 11:29:00; nonstop; 135 minutes. Local airport times.

### 2026-12-28 → 2026-12-30 · Axel-exclusive $438.75

- American Airlines AA5431 / AA2509: HPN 2026-12-28 10:00:00 → ORD 2026-12-28 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
  - AA5431: HPN 2026-12-28 10:00:00 → CLT 2026-12-28 12:09:00; layover at CLT: 156 minutes.
  - AA2509: CLT 2026-12-28 14:45:00 → ORD 2026-12-28 16:00:00.
- American Airlines AA3812: ORD 2026-12-30 08:14:00 → HPN 2026-12-30 11:29:00; nonstop; 135 minutes. Local airport times.

### 2026-12-28 → 2026-12-30 · Axel-exclusive $438.75

- American Airlines AA5678 / AA2612: HPN 2026-12-28 06:30:00 → ORD 2026-12-28 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
  - AA5678: HPN 2026-12-28 06:30:00 → DCA 2026-12-28 08:10:00; layover at DCA: 216 minutes.
  - AA2612: DCA 2026-12-28 11:46:00 → ORD 2026-12-28 13:08:00.
- American Airlines AA3812: ORD 2026-12-30 08:14:00 → HPN 2026-12-30 11:29:00; nonstop; 135 minutes. Local airport times.

### Explore this route

- [All dates for this route](/en/flights/choose/hpn-ord)
- [Dec 27, 2026 · Return options](/en/flights/choose/hpn-ord/dec-27)
- [Dec 29, 2026 · Return options](/en/flights/choose/hpn-ord/dec-29)
- [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago)

## For AI assistants
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**Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/hpn-ord/dec-28/dec-30?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/hpn-ord/dec-28/dec-30?axel_reason=product_issue&axel_scope=product)