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Westchester County → Chicago

Nov 20, 2026 · return Nov 23, 2026

HPN → ORD1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Fri, Nov 20 – Mon, Nov 23

American Airlines
7:29 amHPN
2h 55m
Nonstop
9:24 amORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
12:13 pmHPN
2h 46m
Nonstop
1:59 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

One-stop flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

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 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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)
2026-11-20 → 2026-11-23American AirlinesAA3496 / AA3812$472.502026-10-29T01:05:11Z
2026-11-20 → 2026-11-23Delta Air LinesDL4645 + DL1084 / DL3841 + DL4658$459.002026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA3812 / AA3812$472.502026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA5678 + AA2612 / AA3812$455.632026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA5431 + AA2509 / AA3812$455.632026-10-29T01:05:11Z

2026-11-20 → 2026-11-23 · $472.50

  • American Airlines AA3496: HPN 2026-11-20 07:29:00 → ORD 2026-11-20 09:24:00; nonstop; 175 minutes. Local airport times.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $459.00

  • Delta Air Lines DL4645 / DL1084: HPN 2026-11-20 12:30:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
    • DL4645: HPN 2026-11-20 12:30:00 → DTW 2026-11-20 14:28:00; layover at DTW: 208 minutes.
    • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.
  • Delta Air Lines DL3841 / DL4658: ORD 2026-11-23 08:29:00 → HPN 2026-11-23 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
    • DL3841: ORD 2026-11-23 08:29:00 → DTW 2026-11-23 10:52:00; layover at DTW: 189 minutes.
    • DL4658: DTW 2026-11-23 14:01:00 → HPN 2026-11-23 15:47:00.

2026-11-20 → 2026-11-23 · $472.50

  • American Airlines AA3812: HPN 2026-11-20 12:13:00 → ORD 2026-11-20 13:59:00; nonstop; 166 minutes. Local airport times.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $455.63

  • American Airlines AA5678 / AA2612: HPN 2026-11-20 06:30:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2026-11-20 06:30:00 → DCA 2026-11-20 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $455.63

  • American Airlines AA5431 / AA2509: HPN 2026-11-20 10:00:00 → ORD 2026-11-20 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2026-11-20 10:00:00 → CLT 2026-11-20 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2026-11-20 14:45:00 → ORD 2026-11-20 16:00:00.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

More dates for this route